Bad, bad, bad, bad boy. You make Puff feel so good. Bad, bad, bad, bad boy. He wouldn't change you if he could. (Eh-eh, eh-eh!)

C'mon now, We never took Ma$e seriously as a rap artist, did we? During the Puffy-tization of pop radio in the mid- to late-90s, we were well aware that Sean Combs' main goal was to get us to move our feet and sing along to the hooks, and it didn't matter too much who did the rhyming. There was something charismatic about Ma$e but in a Muppet Show kind of way. We danced the night away to this songs in the Gay Black clubs, yes, but did I ever spend a dime on his mu$ic?

Eh-eh, eh-eh!

"Her face is really hairy, and you can say it's scary. She lives in Mt. Airy, her father's a fairy."

There was a time when that was considered a pretty cool rhyme.

This is the song that started a whole answer record craze in the 80s and we were all in. The story line about a stuck up woman named Roxanne and how she dissed these fine, upstanding fellas kept us running to the store looking to snap up any single or compilation with the word "Roxanne" on it. Most of it was trash. At the end of the day, of all the folks involved in this whole mess, only Roxanne Shanté felt like the real deal, and she wasn't even the "Roxanne" U.T.F.O. was rapping about.

And: Why was Kangol Kid wearing a Samurai sword on the record cover?

When this song rocked Black Teen Night, I don't remember anyone actually doing Pee-Wee's Dance, but this was a beat we did the Fila to like tomorrow was never gonna come. (It did.) Unfortunately, there wasn't a tomorrow for Joeski Love's career as this was his only jam anyone cared about. And we even though we cared a lot, we didn't care for long.

Still, though...Can someone take a minute to at least dedicate a Wiki entry to this one-hit wonder? I would do it myself, but I'm too busy acting like Pee Wee Herman very "stupid-ily".

I got one question and one question only:

What man opens a song about other men's penises with the line "Dave, drop a load on 'em"? I don't know who Dave is, but I would've been down with getting a load from any one of them Naughty By Nature bruthaz back in the day. Phoine! I'm down with O.P.P. as long as one of the Ps belong to 90s-era Treach or Vin Rock. Naturally naughty!

Is it penises or peni? Not sure.

(OK, that was two questions. Forgive me.)

"Crush, kill, destroy, stress!"

Pretty much sums what it must have been like growing up in Queens in the 70s and 80s.

I don't know anything else about Organized Konfusion except that they were out of Queens and that there was something kind of Wu-Tang-y about "Stress", a song that came out one year after Wu's landmark debut.

(And if the group had been called Disorganized Konfusion, that would have also described growing up in Queens.)

Not as talented as Two Tons o' Fun, but for a minute there, The Fat Boys were the biggest rap act out there in both size and popularity. So big were they that they made music with the both Chubby Checker and the Beach Boys. In 1987, they also starred in their own movie "Disorderlies", which unveiled the fraudulent and discriminatory practices in the healthcare system or something. (I'm not sure because I had already tuned the Fat Boys out by '85.).

Most producers sampled "Blind Alley" from The Emotions but producer extraordinaire RZA went with the much more obscure "If You Think It (You May as Well Do It)" for that little twiddling hook throughout the song. (Much-lauded MC Nas was invited to rap and he ends up stealing the show, as he often did back then.)

("Only Built 4 Cuban Linx..." is a fine album, by the way.)

Hey! Look at this—an L.A. rap group with a white guy tucked way in the back. I’m guessing that’s the DJ (Nu-Mark). Nice to see that race relations in the city made some kind of progress after the Rodney King verdict, the L.A. riots and the O.J. Simpson thing-a-majig. Without Jurassic 5's open display of racial harmony, we may have never gotten the historic Kim Kardashian-Ray J. sex tape. You gotta love progress.

There was a time when Timbaland could do no wrong—every beat he dropped sounded like it was beamed in from some distant, impossibly cool planet in the future. That's the planet I always wanted to live on, not this one where a Swedish meatball named PewDiePie is more important than Marcus Garvey. (And Timbaland was the ruler of this cool planet before he met Nelly Furtado who sent his productions down a black hole.)

As for Bubba Sparxxx? He on the record flossin' about something or the other. I’m not about to research who he is or his story, and I’m definitely not wasting time trying to tell him and Fred Durst apart.

I'm just gonna sit back and let this jam launch me into a funky fresh orbit.

“Tell the truth, James Brown was old, ’til Eric and Ra came out with ‘I Got Soul.’” Rude!

That line used to offend me when I was a teenager. The whole point of the song was to defend sampling and show respect for the old-school soul and R&B records that gave hip-hop its backbone. So why take a cheap shot at James Brown—the Godfather, the most sampled man in music history? To me, it felt like blasphemy.

But time and maturity have a way of humbling you. These days I understand the bigger picture…mainly that nobody ever gave a fucc about my opinion on the matter in the first place.

Highly influenced by Schoolly D's "P.S.K. What Does It Mean", Ice-T brought what would be called gangsta rap to the West Coast with "6 in the Morning". N.W.A. and everyone else who clamped on to the so-called gangsta rap subgenre of hip hop owes a debt of gratitude to this Teddy Graham, though many reference Schoolly and Too $hort as the architects of gangsta rap while forgetting to mention T. Before "Straight Outta Compton", "Rhyme Pays" was the cassette we West Coasters rocked that had my parents clutching their pearls in horror. (Just kidding. My folks couldn't have cared less about cursing in my music. They were much more concerned about me going out in public wearing a Guns N Roses t-shirt.).

Along with some members of N.W.A., Ice-T went on to become a mainstay in other genres like thrash metal (as a member of Body Count) and as a television actor. And he's still married Coco, the woman with the huge knockers who graced the cover of T's albums, the same album covers LL said he took "right home to the bathroom" on his magnificent diss track "Break of Dawn". Burn!

These were such innocent times—Roxanne was out here proudly flossin' about rockin’ Reeboks. A few years later, Foxy Brown would be clowning her rivals as nothing but “Reebok broads.” I’m honestly surprised Roxanne didn’t storm the studio with an answer record. Then again, maybe her manager at Forever 21 wouldn’t give her the afternoon off.

Really, including this track is more of a nod to the late, great Howie Tee than anything else, because the song itself hasn’t aged all that gracefully.

But listen close and you’ll catch something interesting: this and Janet Jackson’s “If” both pulled from the same source—John McLaughlin’s “Honky-Tonk Haven.” But more importantly, you can really Reebok to "Bang Zoom". So take THAT, Foxy!

Young MC never got much respect from the hardcore hip-hop crowd, but his Fisher-Price style of rap made a massive dent on pop radio. He opened the floodgates for kids in places like Des Moines to blow their allowance money on cassettes by rap artists instead of Def Leppard. (Well, they still bought the Leppard tapes, too.)

And let’s be real: when his songs came on at the Black Teen Dance, even the hardest ruffnecks couldn’t resist busting a move and doing a hearty Smurf across the floor. I’m not exaggerating—I saw it with my own eyes!

The Irish answer to Cypress Hill, House of Pain surfed the unstoppable Pop Rap wave of the early ’90s—especially across college campuses. Their big hit was basically the soundtrack for frat life, a perfect storm of everything white kids loved: pounding beers, jumping around while spilling those beers on the guy next to them, and sparking bar brawls that left thousands of dollars in property damage.

Us black kids thought twice before we dared jump around, but because those kids were white—nobody went to jail. Nobody even got community service. Just another night of “boys will be boys” in White America with Everlast on the mic.

That friggedy-riggedy rhyming thing Das EFX used to do could tap out your last good nerve after a while—but you’ve got to admit, there was something kinda cool about it too. Borrowing their cadence from Redman and soaking up the production influence of EPMD (who also executive produced their debut), Das EFX hit like a bomb for a hot minute. Both this single and “Mic Checka” shot straight to #1 on the Rap charts, making them feel like the next big thing.

And then, just as suddenly as they ziggedy-zagged onto the scene…they were higgedy-giggedy gone.

I don’t know what Too $hort’s been up to lately, but I’m glad to see he finally spent some $ on dental work he'd been putting off earlier in his career. And I know folks are gonna be grossed out by what I'm about to say, but Imma say it anyway: watching the "Life Is…Too Short" video created some tingling in my loins. I realize if I’d seen him back in the day in one of the cruising bathrooms on campus rocking those tight jeans, I would’ve definitely stepped to him, snaggle-toofs and all. There was something low-key sexy about him—and I’ve always had a weakness for a shorty with a perky little booty in tight jeans.

If we had gotten down, though, I’d have had just one request: skip the BJ. Too many dangerously jagged edges in that mouf. And lucky for him: what I had to give him ain't too $hort.

This is where Kool Moe Dee and Spoonie Gee got their start, though Spoonie bounced before this track was even laid down. Originally released in 1980, right in the thick of the Disco Rap era, “The Body Rock” was one of the first rap records to weave in rock guitars—years before Run-D.M.C. were anointed the Kings of Rock.

But inner turmoil derailed the group, delaying their only album until 1984, by which time Moe Dee was already eyeing a solo lane that would eventually make him a star. Still, “The Body Rock” had legs: Mariah Carey later sampled it for what’s arguably her best single, the Diddy-“produced” Honey. And I use “produced” with air quotes, because we all know Puff was far too busy purchasing baby oil to be spending any real time in the studio.

1988 was a banner year for rap, but the budgets for music videos clearly weren’t keeping pace. Case in point: “Funky Dividends,” which looks like it was storyboarded in a 9th-grade art class. Love it! The track, built around Delegation’s “Oh Honey,” only climbed to #22 on the rap charts, but it made enough noise to get me to buy the parent album "Original Stylin’". I remember absolutely nothing about that record—outside of EST's kooky haircut and the cover art collecting dust on my shelf.

Philly-based rapper EST (real name Robert Waller—I still have no clue what the initials stand for) regularly hyped himself as “the greatest man alive,” and honestly, that swagger worked out for him. When Three Times Dope folded, he pivoted behind the boards and became a sought-after, award-winning producer for acts like Eve, Britney Spears, Beyoncé and Brooke Hogan. (OK, I added that last one just for laughs.)

“I live for the funk, I die for the funk!”

I’m starting to feel a little duped. While digging for this column, I keep uncovering that a surprising number of “hardcore” rappers didn’t come together in some grimy basement with rats and roaches for roommates, but in the cozy dorm rooms of the country's colleges and universities. Turns out the cipher might’ve been held in a rec room, not a housing project hallway. Were their lives as hard-knock as their image suggested? Maybe not. But if this was fraud, it was the good kind—because a lot of these brothers needed those degrees to fall back on once the rap game stopped paying the rent.

Take Lords of the Underground, who formed at Shaw University. Once Marley Marl got involved, they dropped "Here Come the Lords"—a frenetic, near-classic debut that spun off at least four charting singles, including “Funky Child” and “Psycho.” Those tracks hit hard in the streets but also found a home in the gay Black clubs of the Bronx and Manhattan, where the beats and the energy mattered way more than anyone’s backstory.

Heavy D was Pete Rock’s cousin, both of them repping Mount Vernon. In 1990, dancer “Trouble” T Roy (Troy Dixon) died tragically after an accident on tour with his group Heavy D & the Boyz. Pete Rock and CL Smooth immortalized him two years later with “They Reminisce Over You (T.R.O.Y.),” one of hip-hop’s most poignant tributes.

Now, my old roommate swore up and down that Mary J. Blige was the one who taught inner-city kids the word "reminisce". But a little digging shows otherwise: Pete Rock & CL dropped their classic in April 1992, a few months before Mary’s debut album landed in July. And let’s not forget—Blige was from Yonkers, just a stone’s throw from Mount Vernon. Maybe “reminisce” was already floating through Black Westchester slang before they passed it along to the wider world. We salute them for that.

Either way, both camps deserve credit. After all, they didn’t just bless us with timeless music—they probably bumped our SAT scores up a few points, too.

To this day, the only album I’ve ever listened to by the Fugees—or any of its members—is "The Miseducation of Lauryn Hill". And honestly? It’s just aiight. Meanwhile, Pras and Wyclef both have critically acclaimed solo projects, and "The Score" sold a few zillion copies, yet somehow I’ve remained completely unmoved. Am I missing something?

Of all the big singles off "The Score", the only one that ever grabbed me was “Ready or Not”—mostly because of that gorgeous Delfonics lift (“Ready or Not, Here I Come…”) and Wyclef’s delightfully crooked line, “the robbe-REE that I did last WEEK.” A couple of songs from the fellas here and there I can vibe with, but that’s about as far as my Fugees fandom goes.

I know, I know—I’m ridiculously late getting on board with the Fugees. Like, Lauryn-Hill-showing-up-to-the-concert-three-hours-late late. But hey, I’ll get there. Just be patient. Lauryn Hill–fan patient.

Latinos should rap—but just not in Spanish. I’ve wrestled with this for years, trying to figure out why rap en español so often falls flat. My theory? Spanish words almost always end in “a,” “o,” or “-ión,” which makes rhyming child’s play. And when rhyming is too easy, the art suffers—creativity gets lazy because there’s no challenge. Spanish speakers tend to use language to express emotion, while in English rap, the game is all about wordplay acrobatics. The more intricate the lyricism, the more respect you earn. Latinos, by and large, haven’t shown much interest in that kind of linguistic trickery.

But when Latinos rap in English? Está bueno. Big Pun, B-Real, Noreaga and Immortal Technique proved it beyond question. And then you’ve got the Beatnuts—JuJu from the D.R. and Psycho Les from Colombia—holding their own. Still, when you get those two together, throw in Cuban Linx (from Cuba, I'm guessing) and line them up next to Big Pun on “Off the Books,” there's no contest. Pun’s charisma and effortless flow steamrolled everybody. The beat already had extra sauce thanks to samples from The Electric Company and Mabel King (via Melvin Van Peebles), but Big Pun’s verses elevated it into something untouchable.

And a quick word to ICE agents: keep your greasy mitts off bilingual Latinos, or hip-hop’s gonna lose a whole generation of talented rappers.

P.S. Does the name “Beatnuts” sound like a euphemism for bopping the baloney? Am I alone in this?

While everybody in ’88 was busy blasting Public Enemy, Slick Rick, and Big Daddy Kane, MC Hammer was off to the side quietly outselling all of them. His sophomore album "Let’s Get It Started" somehow went double platinum while nobody was paying attention. I look at the four singles from the record and I know them all, but I don’t recall hearing them on the radio, catching a single video on TV, or even once hearing them spun in a club. Outside of “Turn This Mutha Out,” none of the singles made much chart noise.

And here’s the kicker: Hammer’s first album had gone cardboard, yet suddenly he’s racking up two American Music Awards and moving two million copies of a follow-up album that—honestly—feels like it just materialized out of thin air. Where did it come from? How long had it been there before anyone took notice? And why does no one seem to remember it being there?

I don’t have the answers. What I do have, however, is the original "Let’s Get It Started" cassette sitting in my closet, and I have no idea how it got there. I’ve always had a soft spot for “Pump It Up,” but not enough to actually spend money on Hammer.

This situation is starting to feel less like music history and more like some ol' voodoo. And Hammer did call himself the Funky Headhunter at one point...

...this whole thing is starting to freak me out...

Keith Murray’s name pops up absolutely everywhere, yet I still can’t figure out why he’s supposed to be so popular. Sure, he had “The Most Beautifullest Thing in This World,” and that’s all fine and dandy—but beyond that? I’m left scratching my head.

I own the Def Squad CD "El Niño" and it’s a blast, but I naturally gravitate toward Redman’s wildman delivery and Erick Sermon’s production choices. Murray, on the other hand, always struck me more as the jovial sidekick who's always riding shotgun because he doesn't have a car of his own. Murray's probably a great hang—un Niño who’s fun to party with—but his actual legacy as a rapper? That part’s fuzzy. Half the time, I even forget he’s in the group.

Sorry, Keith. I don’t mean to “step through your business and hurt your feelings.”

So Lauryn and Wyclef didn’t exactly part on the best of terms. I once caught an interview with Pras where he played the clueless middleman—claiming he didn’t know what was going down between his bandmates, while slyly admitting he’d “gotten his matters in order” in anticipation of the inevitable breakup. (I guess these matters included the millions of dollars he received from shady foreign sources to make political contributions in the U.S., earning him a 14-year bid in the pokey for illegal lobbying.). I don’t know either Wyclef or Lauryn personally, but if you asked me to weigh in on the drama, I’d have no problem placing the blame squarely on Lauryn.

Every time she pops up in the news, I find myself asking, “Who does she think she is?” Yes, she was a crucial part of the Fugees’ monster success. Yes, she owns the only diamond-certified album by a female rapper. And yes, she delivered this itchy, funky, defiant jam called “Lost Ones” that still bangs to this day. Credit where credit is due. But let’s keep it real—she’s not Shania Twain, she’s not Beyoncé, and she’s not Rihanna. Those women built legacies over decades, taking risks, sometimes even dropping a flop along the way. Lauryn? She’s been living off one project—and a fairly standard one at that—for more than two decades.

Now, I love and respect everyone who considers "The Miseducation of Lauryn Hill" the holy grail of rap and has the patience (and disposable income) to stand around for three hours while she waits for the ghost of Bob Marley to give permission to hit the stage. God bless you all. But me? “Lost Ones” is all the education I need from Lauryn Hill.

And who woulda thunk that Wyclef would end up being the voice of reason among the Fugee members?

I just don’t get why Blacks and Mexicans can’t just drop all the B.S. and get along. One look at the "Gin and Juice" video and it’s obvious the cultures overlap in more ways than one. Sitting drunk in the front yard. Restoring old cars with shiny rims and hydraulics. Grown men cruising around on children's bicycles. The two cultures are almost identical!

There was never any question that Snoop Doggy Dogg (as he was once known) was destined to be a rap star. He stole the show on Dr. Dre’s "The Chronic" in 1991, the same record that poured gasoline on the idiotic—and deadly—East Coast/West Coast feud. In the aftermath of Biggie’s murder, Snoop looked like the next man in line. Some swore his Crip ties protected him, while others doubted his gang credentials altogether. And let’s be honest: pulling cranberry muffins out of the oven with Martha Stewart doesn’t exactly scream “street-certified.”

In the end, the East Coast/West Coast war left no winners: 2Pac, dead. Biggie, dead. Suge and Diddy, locked up. Snoop, Dre, Jay-Z, and Nas eventually morphed into elder statesmen, trading in the street corners for boardrooms and brand deals. I was never the biggest fan of Snoop’s catalog, but I’m glad he dodged the graveyard that executives seemed to think was the best marketing plan for a hip hop artist. Too many other rappers weren’t so lucky.

If anything, we Black folks could stand to emulate the peace-loving spirit of our Mexican cousins—minus that dumb tradition where full-grown men ride double on BMX handlebars. No está bueno.

I know for sure that BT-N-H be saying, “And we pray and we pray every day, every day.” When it comes to the rest of the lyrics, your guess is as good as mine.

Here we are talking about Ohio again—a strange land known as the cradle of funk. But “Tha Crossroads” ain’t that. In fact, when this song dropped, nothing else sounded like it. The prominent rimshot, the slow, haunted rhythm, the lightning-speed harmonic rapping, and that funereal vibe made it feel like a dirge for the seriously smoked out. I might not have known at the time it was a tribute to Eazy-E, but I knew it was about somebody’s dead homiez somewhere.

The style was so unique that even The Notorious B.I.G. had to hop on that shuffling, rapid-fire, tongue-twisting flow for “Notorious Thugs.” I’m not convinced it was his best-est idea ever, but hindsight is 20/20, ain't it? Plenty of folks are still rapping in this style today, but none of them hit the speed, precision, or weird creativity of the original Bone flow.

And what must Bone Thugs-N-Harmony concerts have been like? I imagine you’d need to bring a whole napsack of lighters just to hold up from start to finish.

Again, I have to call out the fact that not all hip-hoppers came from the mean streets. Dead Prez are ultra-political and revolutionary, so of course these viewpoints were fortified in the Black Student Union of an HBCU. (FAMU to be exact). Brooklyn's M-1 and Atlanta's stic.man met on the university campus in the 90s and by 2000, they had released the near-classic "Let's Get Free" containing earlier released singles and new material produced by them, including the charging and bombastic "I'm a African" and a different take on "Hip Hop", "It's Bigger than Hip-Hop" with production by Kanye West, which is just as good as the original. The groove here buzzes near your ear like a hornet's nest, but in the best way possible.

[I often wonder what my life would be like if I had known what a HBCU was when I lived in Arizona. I sometime get a heavy sense of having missed out on a lot...(insert sad face emoji here).].

Back in the day, I wasn't familiar with this brand of bright, granola-inspired rap spearheaded by the Native Tongue consortium, as the narrative in 1988 was ruled by confrontational artists like N.W.A. and Public Enemy. Still, groups like De La Soul, A Tribe Called Quest, Mos Def and Black Sheep gave us some of the era's best albums while the Jungle Brothers contributed with solid singles like "Because I Got It Like That" with its prominent Sly and the Family Stone sample, and pro-Black anthems like "Doin' Our Own Dang".

When you listen to "Because I Got It Like That", they shout out all the cities that got it like that, and you might notice that my hometown of Phoenix was conspicuously left off the list. I'm here to tell you that we definitely didn't have it like that as I can't imagine the Jungle Brothers selling a single record in the 1980s Arizona, Home of the anti-MLK Holiday government. If we couldn't get one lousy Monday off to celebrate Dr. King, there was no way a Jungle Brother would get played on the radio.

“Buffalo Gals” was produced by Trevor Horn, the same (white) guy who produced “A Kiss from a Rose.” How is that possible?

This is one of those videos that convinced me everybody in New York was breakdancing at all times, which honestly terrified me because I absolutely stunk at it. I figured if I ever moved to that city, I’d need to live on the block where everybody was doing the Reebok.

Rap music felt like a dream to us back then—the whole hip hop culture did. My brother watched "Beat Street" about a thousand times and still, to this day, dreams of visiting New York City in hopes that it's still gritty and raw. It isn't. When I worked in East New York back in 2019, he used to ask if I ever ran into Jeru the Damaja. If Jeru was making egg, bacon and cheese sammitches at the bodega on Pennsylvania Ave, then yeah—maybe I did.

“Buffalo Gals,” created and conceptualized by two white Brits in collaboration with New York’s World’s Famous Supreme Team, is a perfect example of Europe’s fascination with Black American cultural expression. People say the Brits and the French are rude to Americans, and that’s only partially true. They’re rude to white Americans. They often treat us Black folks like the Kings and Queens we are.

De La Soul did a bang-up job representing the Funny Black consortium long before anybody had the language to define it. Cerebral and cheeky, songs like “Me Myself and I” announced to the world that—just like white folks—the Black population also included dudes who were awkward, introspective, and sometimes felt like aliens on their own planet. This off-kilter rap eventually sparked a lot of pushback from people who were uncomfortable with Black men not sticking to the routine, ghetto-inspired imagery hip hop was expected to churn out.

Most folks couldn’t be bothered to understand the D.A.I.S.Y. philosophy, so they just called De La a bunch of hippies and kept it moving. (The literal daisies in their artwork didn’t help their case.)

Today it’s hard to understand why this deviation from the norm caused such a fuss, but it did—enough that De La ditched the whole D.A.I.S.Y. motif for their sophomore album, "De La Soul Is Dead."

And look, De La Soul caught a lot of flak back then, but let’s be honest: it was really those copycat, sissy-poo P.M. Dawn boys who ruined everything for them and everybody else because De La Soul's music--especially their debut record--was the real deal. And still is.

Yum! I love lox—especially with cream cheese and capers on a bagel, paired with a hot cup of coffee and…

What?
What’s that you say?
The Lox is an American hip hop trio composed of East Coast rappers Sheek Louch, Styles P, and Jadakiss?

Oh. Well, I do like Jadakiss’ flow, and I genuinely did not know The LOX were made up of three people—but OK, noted.

And honestly, why did people keep inviting DMX onto their records? The man steps on a track and sucks up all the attention with all that charismatic barking and growling.

On this track, are Tek and Steele referring to Bucktown in Iowa, that historic little pocket on the east end of downtown Davenport?
Probably not.

Tek and Steele first hit the scene as part of Black Moon’s "Enta Da Stage", then branched out for their own 1995 debut, "Dah Shinin’". Their arrival helped solidify that mid-90s “intelligent gangsta” movement—dark, unvarnished, matte-finished hip hop that reflected the bleak realities of New York just as the city was morphing into the Disney-fied playground we know today.

Smif-N-Wessun famously caught a cease-and-desist from the Smith & Wesson firearms company, which forced them to change their name to Cocoa Brovaz in 1996—a name they used on their 1998 album "The Rude Awakening".

I don’t know if Palmer’s (makers of that cocoa butter we all loved) ever sent a letter too over their new name, but the duo eventually went right back to being Smif-N-Wessun for their later releases. And I’m still waiting to hear if Stephen King plans to sue over their first album title.

With all those spelling acrobatics in their song titles, Webster’s Dictionary probably should’ve filed paperwork as well.

During this era, DJs—whose bones had grown strong from sucking at the now-sagging teats of George Clinton and James Brown—started branching out, digging deeper into the crates of their uncles’ jazz collections for new flavors to sample. In O.C.’s case, he leaned on Les DeMerle’s A Day in the Life, an early-’70s gem from the Brooklyn-based jazz fusion drummer and vocalist.

Kool G Rap-esque in delivery and orbiting the same circles as Nas—with DJ Premier in his corner—O.C. somehow never became a household name. Brooklyn in the mid-90s was bursting at the seams with razor-sharp MCs, so it’s no surprise that O.C., and this excellent single, slipped through the cracks.

It’s a hot track, no question. But my personal #1 from O.C. will always be “Return of the Crooklyn Dodgers,” alongside Jeru and Chubb Rock, produced by DJ Premier and sounding like peak New York bottled in three minutes.

“Check baby, check baby 1-2-3-4.”

This Teddy Riley–produced joint used to absolutely detonate the club. And this was at the white club where I worked as a bouncer, of all things. The white girls would shake whatever they had (which wasn’t much), and the drunk white boys would creep up behind them and rub their little penises against the general region where an ass was supposed to be. Me and the other Black guys working the floor would point, cackle, and pretend we were too busy protecting their lives to notice. But trust—we noticed.

“Rump Shaker” is a pure party record—not designed to heal the racial wounds of the last three or four centuries—but it definitely did its part in bringing folks together for some wholesome, vertical dry-humping in public spaces.

Man! Those were the dayz. Thank you, Teddy, for supplying the soundtrack that gave the handful of Black dudes at the Uni some truly unforgettable bonding moments.

Special Ed—not to be confused with late, shirtless hunk Big Ed the Assassin or Special K, the cereal—hit the scene with the Howie Tee–produced “I Got It Made,” boasting about his treaty with Tahiti and his fleet of 74 Honda scooters. The video was shot all around Brooklyn: the Public Library, Grand Army Plaza, what looks suspiciously like Riis Beach, and even a high school in session. In my humble opinion, those kids should’ve been in class learning what a treaty actually is instead of outside doing the Roger Rabbit, but hey—Brooklyn gon' be Brooklyn.

Special Ed came to us with his Indo-Caribbean good looks and the tight, uncomplicated rhymes of the era. “I Got It Made” was catchy as all get-out, but neither the track nor the artist were really built to survive beyond those first few singles. Hip hop was sprinting away from the non-aggressive, relatively insipid stylings of Ed, Joeski Love, and Kwamé with those fuckin’ polka dots. We know Kwamé reinvented himself and became a successful producer. As for Special Ed, I just hope he managed to sell those scooters or land a diplomatic gig in Tahiti—as per the terms of their agreement.

Just because “Rapper’s Delight” is a pioneering rap single doesn’t mean it’s the best. But like every other genre’s “first,” it deserves its flowers. Nobody’s placing Big Bank Hank on the same lyrical tier as Eminem or Jay-Z, but let’s be real: those giants don’t climb as high without “Rapper’s Delight” laying the the groundwork to the pop charts.

The track is basically three neighborhood dudes tossing funhouse rhymes over the breakdown of Chic’s “Good Times.” They brag about dressing “viciously” like Muhammad Ali and complain about soggy macaroni at a friend’s house—lightyears away from the ultra-curated menace, trauma, and flexing that fill the genre today. And as simple as their bars sound, we now know that many were bitten from other local MCs.

“Rapper’s Delight” didn’t instantly blow the doors open for pop crossover—neither for the group nor for rap as a whole. What it did do was till the soil. It made space for Kurtis Blow to sign to a major label, for Whodini to go platinum, for Run-DMC to hit regular rotation on MTV. The record itself isn’t some avant-garde masterpiece, but Sugarhill Records president Sylvia Robinson pulled off one of the savviest marketing moves in pop-music history. It’s a true David-and-Goliath moment where the underdog actually wins.

The Sugarhill Gang would go on to release tighter singles like “Jump On It” and "Apache" but “Rapper’s Delight” lives forever—not only for what it kicked off, but for how future hits (hello, “Aserejé” by Las Ketchup) used it as DNA. And honestly, what would the English language even be without “hotel, motel, Holiday Inn”?

Preemo rules over this list, just as he should. And here we have DJ Premier linking up with Mos Def from the Planet of Brooklyn—a cosmic alignment of boom-bap precision grounded in streetwise wisdom.

Mos Def, now known as Yasiin Bey, always carried a strident but non-confrontational rap style. As the oldest of twelve children, you can almost hear the big-brother energy in his delivery: firm, patient, instructive. That tone runs all through “Mathematics” and stretches across his breakthrough debut "Black on Both Sides."

On “Mathematics,” Bey breaks down the plight of Black folks, poor folks, and poor Black folks through a barrage of statistics we gloss over every day. He built his name on observational, educational rap— the kind of truth-telling that might get waved off today as conspiratorial or “fake news,” especially by those who prefer to believe Black people are the sole architects of every problem we face. Bey pushes back with receipts. The numbers are there, he says, if you’re willing to look, willing to interpret, willing to see beyond your own comfort.

But he also knows the trick: an unequal, segregationist education system trains poor and Black kids to fear numbers before they’ve even mastered them. And when you’re taught to avoid the math, you’re that much more likely to become part of it—another data point in someone else’s chart, another statistic in a country that pretends numbers don’t lie even when the people reporting them do.

Common wrote this one about sexual fantasies while hanging around pre-mental-Blitzkrieg Kanye and John Mayer—yes, Taylor Swift's former sperm donor—who croons the “go!” hook and somehow walks away with a songwriting credit for it. At the time, Common was still licking his wounds after the commercial and critical wobble of his bloated, overly-ambitious "Electric Circus", an album many felt proved he’d wandered too far into the abstract. (And not the good Abstract, like Q-Tip.) His 2005 comeback "Be" was the antidote: lean, focused, and unmistakably grounded, thanks to Ye's steady hand behind the boards.

“Go!” arrived as the album’s third single and its breakout success, propelled by Linda Lewis samples and a clean loop from DJ Paul Nice. But the real engine is that jittery, kinetic drum pattern—always moving, always nudging Common forward—giving him room to deliver his verses with real spark.

Now, Common is undeniably a cute Teddy Graham, but I’ve never clocked him as a sexual figure, which makes the lyrical content—raw bathroom sex, threesomes, the whole horny vignette—feel slightly left of center compared to his earlier, more cerebral work. Still, everything locks perfectly into place here. Even John Mayer’s cameo didn't bug me...somehow.

Our first knee-jerk reaction to the tough, beautiful Eve was that she was the new Little Red Rappin’ Dyke on the hip-hop block. But as time went on, she softened her image and joined the ranks of talented women like Latifah, Lyte, and Missy—women who practically had to put in hundreds of overtime hours just to swat away the ever-circulating lesbian rumors. (Well, Latifah didn't work so hard.) In rap, if you didn’t go full on Lil’ Kim Slutbucket, folks were ready to stamp you with the L-word before the second verse even hit.

Or—you could just drop a bomb-ass single produced by a nigga with attitude Dr. Dre, who’s also had to shimmy around gay rumors his entire illustrious career. “Let Me Blow Ya Mind” is pure Dre magic: sparse, itchy, irresistible production with that slow-burn confidence he perfected. And then Gwen Stefani pops up—literally rolling in on the back of an ATV—to lace the hook. The whole thing is a win from every angle.

Eve never let the lesbian chatter bother her. She eventually married her longtime sugar daddy, a super-rich Brit entrepreneur whose net worth is right there in his first name: Maximillion Cooper. Some folks side-eyed her for going Hollywood and marrying a white man, but listen—this man founded a half-a-billion-dollar company. If you’re clowning Eve for securing that level of financial bliss, you need to fall back and take a knee, jerk.

First and foremost, Busta’s vocal-cord-shredding delivery—whether with Leaders of the New School or during those early solo years—was thrilling, bombastic, and absolutely impossible to sustain over a whole career. There isn't enough lemon tea with honey on earth that can let your throat scream with that level of intensity through three presidencies.

I’m not sure Busta’s name belongs in the cathedral of the all-time MCs, but I’ve always loved the way he’d run entire stanzas off the same rhyme—Tom Cruise, fuse, who’s, ill street blues, residues—. Those were fun as hell to rap along to while Bankheading across a sticky club floor at 2 a.m.

“Woo Hah!!” was one of those wonderfully weird club grenades that detonated the moment the DJ set the needle down. It was a real shift from the more socially conscious vibe of Leaders of the New School, but strategically? Brilliant. It helped launch Busta into full-on modern rap stardom.

And of course the video came straight out of the era when every hip-hop visual that mattered was directed by Blatino auteur Hype Williams, who crafted sixteen of Busta’s videos (and twenty for Ye). The whole thing is dipped in that late-90s/early-2000s cartoon-bling aesthetic—fish-eye lenses, curved-camera sweeps, and enough gloss to laminate a Buick. Or the pouty lips of a room full of drag queens.

Busta became essential to hip hop’s mainstream takeover in the nineties, giving us dancefloor gems like “Woo Hah!!,” “Dangerous,” and “Put Your Hands Where My Eyes Could See.” But he also found himself in controversy when, after being asked about homosexuality in hip hop, he shut the whole thing down, voiced his disapproval, and stormed off. Oh, the drama!

Now, I’m not saying anything about anybody, but when a man performs an exit that dramatic when asked about gay shit, it leads me to believe that being in "Flipmode" just might be code for one's willingness to top or bottom with equal dexterity. Just sayin'.

BTW, Busta did come out later to publicly support Frank Ocean, so he gets his propers. Also, we know Busta isn't gay because he didn't keep his waistline in check over the years, a serious no-no for a true gay daddy.

Here we are talking about Howie Tee once again—a major glow-up from the clankity-clank work he did with The Real Roxanne.

Music is stuffed to the rafters with one-hit wonders, and rap is no exception. Luckily, Chubb Rock dodged that fate with four respectable #1s on the Rap charts, including the groovy-ass “Just the Two of Us,” released before “Treat ’Em Right.” But it was that second single that turned Chubb into a bona fide rap star—and introduced me to First Choice’s “Love Thang” in the process.

Chubb belonged to that small-but-mighty consortium of artists pushing positive rap: low on cussing, high on optimism, but still fully Running-Man-able thanks to Tee’s sample of James Brown’s “There Was a Time.” And Brooklyn’s own Chubb Rock wasn’t just book-smart—he actually left Brown University to pursue rap. Early success came fast, but once the momentum cooled, he transitioned into radio, showed up on television and found a second act down in Hotlanta.

I’ve said it before, but it deserves instant replay: Chubb pops up on “Return of the Crooklyn Dodgers,” a scorching Preemo-produced track from the "Clockers" soundtrack. He was part of the rotating roster for the second iteration of Crooklyn Dodgers, alongside O.C. and Jeru the Damaja. (And yes—Chubb curses on it!)

Whether Chubb should’ve stayed at one of the world’s most prestigious universities is a debate scholars will dispute over for years to come. But one thing is certain: when he linked up with Howie Tee and later with Preemo, Chubb was one of the important Rocks out there—right up there with Chris, Kid, and “The.”

When Mix-A-Lot talks about being on Broadway but the Taco Bell is closed, the girly on his tip suggests, “Go back the other way, we’ll stop and eat at Dick’s.” Then he delivers the immortal line: “Dick’s is the place where the cool hang out.”

This always struck me as hilarious because after the Black Teen Dance in Arizona, we would all pile into our cars, drive straight to Dick’s, and hang out eating burgers while blasting music as loud as our subwoofers allowed. So imagine my surprise when digging around for this song, I learned that the inspiration actually came from a trip Sir Mix-a-Lot took to Arizona. Could this be the only known instance of Arizona having a positive impact on rap? The state might want to put that on a license plate.

Sir Mix-A-Lot hails from Seattle—a city not exactly known for hip hop in the late ’80s—but his music definitely carried that West Coast DNA: sparse production, earthquake bass, lyrics sprinkled with little pockets of goofball brilliance. His songs were built for cruising the ave “with five fellas and 22 freaks.” I just checked the math and that’s 27 people, Sir Mix. Was your posse rolling down Broadway in a school bus?

But the details don’t matter—the vibe does. And the vibe on “Posse on Broadway” is undeniable. Sir Mix’s nasal monotone fits the bottom-heavy groove like custom upholstery. It’s a song engineered to blow out the speakers in your Jeep and to make every parking lot feel like a block party. Forget “Smells Like Teen Spirit”—this is what put Seattle on the musical map.

Of course, Sir Mix-A-Lot is best known for 1992’s “Baby Got Back,” which snagged a Grammy for Best Solo Rap Performance. People love to clown that win, but let’s examine what it was up against: MC Hammer’s “Addams Groove,” Queen Latifah’s “Latifah’s Had It Up 2 Here,” LL Cool J’s “Strictly Business,” and Marky Mark and the Funky Bunch’s “You Gotta Believe.” I woulda also picked "Baby Got Back" out of that pitiful line-up.

Meanwhile, the Recording Academy completely ignored these other singles that came out in 1992:
• “Tennessee” – Arrested Development
• “Jump” – Kris Kross
• “Mind Playing Tricks on Me” – Geto Boys (a masterpiece!)

("Nuthin' But a 'G' Thang" was released as a single in January of 1993, making it ineligible for Grammy consideration that year, though "Let Me Ride" took home the award in '94.)

But the Grammy committee? Ugh. What a bunch of Dick's.

We were country folk, so we didn’t suffer from the breaks the way kids growing up in the inner city did—or at least that’s how it felt at the time. In fact, kids my age didn’t even know what the word meant. One kid in my grade just substituted the only word he did know, running around the playground chanting, “These are the boogies! Break it up, break it up, break it up, break down!”

I knew damn well that wasn’t what Kurtis Blow was saying, but I wasn’t exactly in a position to correct him. Truth is, I didn’t know what “the breaks” were either.

What I did know is that we somehow had two or three Kurtis Blow albums in the house, which was a real coup considering how hard it was back then to get anything from a rap artist that wasn’t a random 12-inch single. Rap wasn’t what it is now—far from it. Blow was the face of disco rap, a style built with analog instruments, live musicians, and background singers, closer to dance-pop than street reportage.

So it’s no mystery why “The Breaks” cracked the Top 100, climbed to #4 on the R&B charts, and became the first rap single to go gold. This was a full-on dance record: catchy hook, undeniable groove, and a beat engineered to move feet. Kurtis delivered it all with a friendly, open charisma that didn’t send white radio listeners scrambling for the dial. In that sense, he was a more palatable ambassador for rap than the Sugarhill Gang, whose rhymes—fair or not—could come off a little cartoonish to mainstream ears.

Eventually, technology arrived, producers evolved, and disco rap was wiped off the map. But not before it gave us rap’s first true superstar in Kurtis Blow—a man with the magnetism, intelligence, and good looks that made him the perfect recipient of Mercury Records’ promotional dollars. When his moment passed, he handed the baton to Run-D.M.C., who would push rap into louder, harder, and far more revolutionary territory.

Yes, the ’80s were a time of some major boogies indeed.

My first exposure to Salt-N-Pepa came via “The Show Stoppa (Is Stupid Fresh),” buried on a rap compilation album that somehow found its way into our house. At the time, they called themselves Super Nature, having recorded the track as a class project for Hurby “Luv Bug” Azor. The song eventually landed in Marley Marl’s hands, got spun during his radio sets, and—against all odds—turned into a modest hit.

The first time I saw Salt-N-Pepa, though, was with the video for “Tramp” on BET (or possibly Night Trax—the memory’s fuzzy). I was instantly hooked. I had already been introduced to Roxanne Shanté on record, but I hadn’t really seen her—or any other female rappers—on television yet. With their short haircuts swept dramatically to the left, Salt, Pepa, Spinderella, and Hurby Luv Bug presented something visually and sonically new, and it didn’t take long for that image to make waves across multiple charts.

The remix of “Push It” belongs on the short list of rap’s true crossover flashpoints—right up there with “Walk This Way” and “U Can’t Touch This”—moments that snapped hip hop straight into Walkmans everywhere, even places as desolate as Des Moines.

But before any of that could happen, Salt-N-Pepa needed a record to crack Black radio, and “Tramp” did the job—at least briefly. Built on the Otis Redding and Carla Thomas version of Lowell Fulson’s 1966 hit, the song gave them their first real foothold and set the stage for what was coming next. It was fun, funky and catch as all get-out. I absolutely loved this song!

Salt-N-Pepa never really positioned themselves as rappers chasing street credibility the way MC Lyte, Queen Latifah, or Yo-Yo did. Their lyrical approach was lighter, more accessible, and aimed squarely at the pop charts from jump. Rap purists may still debate that strategy, but there’s no denying its effectiveness. Salt-N-Pepa played a major role in expanding rap’s crossover appeal, and without “Tramp,” there likely wouldn’t have been a “Push It.”

Ironically, “Push It” started life as the B-side to “Tramp,” a quick dance track the group slapped together. DJs, however, gravitated to the flip, prompting a more radio-friendly remix by Cameron Paul. Once “Push It” exploded, “Tramp” was quietly swept out to sea in its wake—but its role as the spark that lit the fuse shouldn’t be forgotten.

Salt-N-Pepa went on to much bigger things after "Tramp", eventually being enshrined in the Rock and Roll Hall of Fame in the Musical Influence category in 2025. Whenever rap artists are inducted into the RRHOF, it's like getting the Accountant of the Year plaque even though you've worked in the marketing department all these years. But an honor is an honor, and S-N-P are definitely deserved of all the accolades they've received.

Due to sampling clearance issues, the song didn’t receive an official release until a full decade later, finally surfacing in 2017 on Tragedy Khadafi’s album "The Kuwait Tapes". (What kind of stage name is Tragedy Khadafi? Does he realize that Muammar al Khadafi was still alive when they fucked him with a bayonette after being pulled him from a sewage pipe? He shoulda stuck with his original stage name, Intelligent Rapper.)

“Calm Down” is yet another Marley Marl gem, built around a tinkling piano line that drops you straight into the overwrought drama of a daytime soap opera. It sounds melodramatic because it is—the sample comes from a song produced by certified swish-master Barry Manilow. Leave it to Marley to turn middle-of-the-road adult contemporary into street-level tension.

N.O.R.E. (and yes, I only recently learned that N.O.R.E. was once Noreaga—I know, I know…) was embroiled in a beef with Nas at the time. But honestly, has there ever been a moment in hip-hop history when Nas wasn’t beefing with somebody? The man has more beef than that old Wendy's woman.

What really surprised me was learning that the sparse, skeletal beat came from Marley Marl. This sound is worlds away from the dense, layered productions he crafted years earlier for Kane, Kool G Rap, and LL Cool J. It’s minimalist, tense, and confident—proof that Marley didn’t need clutter to command attention.

Black Puerto Rican Noreaga drops a Spanglish-laced verse that works better than expected, adding texture and personality. Still, Nas does what Nas always does: steals the show effortlessly. His intricate yet unbothered delivery reminds you why he’s a permanent fixture in rap’s upper echelon—calm, precise, and untouchable. And his off-key singing is kinda fun, too.

One of my favorite YouTube rabbit holes is listening to artists recount everything they had to endure just to get Ol’ Dirty Bastard into the studio to bless their singles—or, in some cases, out of it. Pras’ experience while recording “Ghetto Supastar” falls squarely into the latter category.

You really can’t blame Dirty for wanting to jump on a record this funky. Even the decision to flip the Dolly Parton/Kenny Rogers country-pop crossover classic for the hook was inspired. If there’s a weak link here, it’s Mýa’s eek!-a-mouse vocals, which I found annoying even back then. I know she was considered hot at the time, but the exact reasons have always escaped me.

What makes the story even better is Pras openly admitting that he didn’t want ODB on the record at all. The problem was that Dirty showed up at Pras’ studio completely unannounced—and then simply refused to leave. When ODB heard the backing track, he decided on the spot that he was going to be on it, finished or not. End of discussion.

The wildest part? ODB wasn’t just in the wrong studio that day—he was in the wrong city. Pras was recording in Los Angeles. ODB was supposed to be in New York. Somehow, Dirty ended up on the opposite coast and didn’t appear to realize it. How he got to L.A., why no one stopped him, and how he didn’t notice he was 3,000 miles off course is anybody’s guess. But stories like that are exactly why people still love ODB long after he’s gone.

ODB died far too young, and Pras later found himself serving a lengthy prison sentence for white-collar crimes that plenty of other folks—especially white folks—often skate past with little more than a wrist slap, if that. Superstar status didn’t protect him; in the end, Pras got treated like a straight-up 'fugee’d by the Trump-annointed U.S. court judges.

Hip hop history is cruel like that—but I'll be damned if it isn’t unforgettable.

A cousin of Marvin Gaye and an almost auxiliary member of the Wu-Tang Clan, I have to admit that while I clocked how much of "Made in Brooklyn" sounded Tang-adjacent, I wasn’t fully aware at the time that Masta Killa was actually an official member of the group. That confusion is understandable: on "Enter the Wu-Tang (36 Chambers)", he only shows up for a single verse on a single track. Back then, he was very much a rapper-in-development, quietly being groomed under the watchful eye of the GZA.

While it doesn’t enjoy the same acclaim as his 2004 debut "No Said Date", "Made in Brooklyn" is a solid outing, and a big reason why is the raw, demo-like feel of “Brooklyn King.” The rapping cuts out abruptly in spots, and the drumming sounds like it might’ve been handled by a high school drum majorette trying to impress an onlooker. It’s pure throwback—Rakim energy filtered through early Def Jam minimalism: just drums and bars, no frills, no polish.

“Brooklyn King” technically lives as the B-side to “It’s What It Is” (featuring Raekwon and Ghostface Killah), which means it probably shouldn’t qualify for this list. But given how often my negligent ass has ignored that rule, you’d be forgiven for thinking my last name is Nixon.

But Anita Baker said it back in 1988 and Auntie Nita never lies: "rules are made to be broken." And when a track bangs this hard, the rule-breaker that lives in me deserves a full pardon, just like Tricky Dick got back in the day.

Some of y’all may not remember (or ever know) Group Home, but once you lay eyes on one half of that duo—aspiring boxer with the aggressively Christmas-coded stage name Malachi the Nutcracker—you’ll immediately think: forget that holiday-ass nickname. A nigga that fine should’ve been called Malachi the Nutbusser. He might have you remixing old-time church standards into something a little more… personal, singing “O Cum On Me, Faithful, boy-ful and triumphant!” as he slides down your chimney.

Malachi was literally taken off the street and absorbed into the Gang Starr Foundation, and according to hip-hop lore, DJ Premier played a pivotal role in keeping him out of prison. The story goes that Preemo made a deal with the judge: he’d keep Malachi out of trouble by putting him to work—cutting an album around him—even though Malachi had never rapped a day in his life. Whether that’s courtroom fact or hip-hop mythology, what is true is that everything worked out.

The result was 1995’s "Livin’ Proof", an album that quietly stands as one of the most underrated releases of the era. Malachi avoided prison time, Group Home entered the rap conversation, and Premier delivered a masterclass in stripped-down boom bap. Though Group Home never reached the same level of notoriety as other New York duos of the mid-’90s, Premier himself has cited "Livin’ Proof" as one of his strongest full-album productions—and the title track is a huge reason why.

“Livin’ Proof” is classic Preemo minimalism: cold drums, moody loops, no wasted space. And while Lil’ Dap handled most of the lyrical heavy lifting, Malachi’s presence—both visual and otherwise—was undeniable. If you need proof (no pun intended), check out their “Supa Star” video for some preemo eye candy. Good Lord ah-mighty what a nut-crackin' good time to watch Melachi in those old videos.

Beyond the visuals, the entire "Livin’ Proof" album is essential listening for anyone who worships at the altar of DJ Premier, by the wau.

And if you want to go deeper, definitely check out the “So Wassup?” YouTube series, where Preemo breaks down how he crafted his magic on classic tracks. Watching him dissect records like these only reinforces why "Livin’ Proof" still lives up to its name.

Music really does save lives, and even better if doing so sets fine-ass boxers who accidentally become rappers under our Christmas tree. Hallelujah!

I’m not sure this is my favorite Brand Nubian song. For example, the first single and DJ Premier–produced “The Return” might actually be more enjoyable on a purely visceral level. But “Don’t Let It Go to Your Head” is one of those iconic rap records where leaving it off a list like this would feel downright sacrilegious.

And trust me, omitting “The Return” was not easy. That Preemo beat knocks, and it’s packed with classic Grand Puba one-liners like “rhyme flow stay off the meter, tight like two-seaters / make y’all get nuts like a cell block filled with dick beaters.” Lines like that make me seriously question my curatorial integrity, but I'm gonna stick with "Don't Let It Go to Your Head".

“Don’t Let It Go to Your Head” earns its place by being a sharp cautionary tale aimed at rap crews who achieve quick, Hammer-like fame—warning them that sustained success in the music business is even more fleeting than a gay sauna romance, and only about half as satisfying. Taking from the 1978 Jean Carn gem of the same name, the song is not a club banger, but rather a laid back groove meant to be bumped as you chill in a quiet lounge or while cruising up the FDR on a warm summer night with your main squeeze, Big Booty Rudy.

A Tribe Called Quest had already explored this territory with their 1991 gem “Show Business” from "The Low End Theory", but Brand Nubian approached the topic with a sharper edge and a heavier dose of grown-man wisdom. The MC Hammer phenomenon had flipped the entire rap industry on its head, prompting artists like Public Enemy and Ice Cube to loudly declare they’d rather “get the hell out before they sell out.”

Chuck D largely stayed true to that promise. Flava Flav… well, Flav eventually became a cheese-doodl reality TV mascot. And Ice Cube pulled off one of the most jaw-dropping career pivots in popular culture, going from “I Wanna Kill Sam” (referring to our Uncle) to engaging with Trump.

Actually, scratch that—the Trump thing ain't no real biggie. It was the “Are We There Yet?” films that marked the final destination on Cube’s road Sell-Out Country.

That said, Cube wasn’t one of the artists Brand Nubian had in mind when they recorded “Don’t Let It Go to Your Head.” At the time, he was still very much aligned with the militant, uncompromising image he helped create. This song was aimed squarely at the Johnny-come-latelies—the rappers who caught one or two hits, started believing their own hype, and let all the adulation mess up their brains.

In that sense, “Don’t Let It Go to Your Head” isn’t just a song—it’s a sermon. And like all good sermons, it still hits uncomfortably close to home for many decades later.

Busta Rhymes was never built to be a solo artist—at least not with that rapping style. When you’re young, hungry, and trying to separate yourself from the pack, you’re willing to burst a blood vessel just to get noticed. But even back then, Busta seemed to understand that going full Tasmanian Devil for an entire album would be unsustainable. Sixteen bars? Perfect. Sixty minutes? Somebody gonna end up in I.C.U.

Before he went out on his own, Busta was part of Long Island's Leaders of the New School, a group rooted in that earthy, around-the-way, Afrocentric rap that defined the Native Tongues movement. That whole vibe felt especially foreign to those of us who grew up on the HBCU-less side of the Ole Mississip. Tracks like “Classic Material” knocked hard thanks to their Ohio Players and Young-Holt Unlimited samples—key ingredients in the jazz-fusion-heavy rap sound of the early ’90s. This was a sound equally suitable for the dancefloor and a night out with the boys.

And, as usual, Busta steals the show. Something everyone knew—except Charlie Brown—from jump street.

In fact, L.O.N.S. had already broken up several times before they even got out the gate properly. Internal tension was constant, largely because Charlie Brown saw himself as the group’s leader—a role Busta also claimed. According to the unwritten laws of pop culture, Charlie should have been the focal point: He had hair blessed with loose curls. He was lighter-skindid. He was more conventionally attractive and clearly comfortable taking his shirt off in videos (a practice he honestly should have leaned into a lot more).

But charisma doesn’t follow logic. Busta’s wild energy, unmistakable voice, and rapidly evolving style—plus his constant cameos on scorching A Tribe Called Quest tracks—made him the obvious star. Soon enough, he was commanding attention at shows and press appearances, which ultimately led to the group’s very public implosion… on Yo! MTV Raps, no less. When that happened, Fab Five Freddy was not ready.

The group eventually reunited in 2012, and—plot twist—it was Dinco D, the L.O.N.S. member no one ever talks about, who aged the most gracefully. Charlie Brown was looking like the cartoon version of Charlie Brown. Thank God he kept his shirt on this time.

And notice how Busta started gaining weight once he abandoned that calorie-incinerating rapping style?

Oh my gawsh.

You know why white folks are the way they are sometimes? Because they don’t have coping strategies. Minorities are constantly dealing with some kind of bullshit, so we develop sharp survival skills—little mental tools we deploy so we can move on to the next trial or tribulation. But ask Eminem for an autograph and suddenly a table is flying across the room. Chill out, dude. It can’t be that traumatic to have hundreds of millions of dollars sitting comfortably in the credit union.

People always ask whether Eminem deserves to be included in the “greatest MCs of all time” conversation. How the hell should I know? That ain't really none of my beeswax, and I don't need him writing no blistering diss track about me if I give an answer he don't like.

But no great rapper exists in a vacuum, and Eminem has never been shy about citing his influences—most notably Treach from Naughty By Nature. You can hear it in the breathless urgency, the rapid-fire precision, the refusal to coast. Even the hook on this track tips its hat directly to another influential legend, Rakim: “I’m the R, the A to the K-I-M / If I wasn’t, then why would I say I am?” That lineage matters.

Choosing an Eminem song for this list was easy mainly because I know so few of his songs. His rhyme schemes demand an amount of undivided attention that I simply don’t have lying around. I downloaded his biggest albums decades ago and still haven’t given them the focus they deserve—between going to work and keeping a balcony full of plants watered, something had to give.

But what was immediately clear is that songs like “The Way I Am” come from a very real place. Even if the average Joe can’t relate to being stalked by fans or suffocated by fame, the frustration is authentic. This isn’t cosplay or a clever gimmick for Eminem—it’s personal. And audiences, Black and white alike, picked up on that instantly. His technical ability scared the hell out of people, to the point where even beef-hungry MCs decided maybe this was one fight they’d rather not have.

The line about radio not even playing his records still makes me giggle, because even from under my coconut tree in Colombia, his videos were damn near unavoidable. When you’ve sold something in the neighborhood of 200 million records worldwide, trust me—radio is playing your jam, just like everybody else.

You don’t have to like Eminem. You don’t even have to understand him. But pretending his talent, influence, and sheer technical terror didn’t shift the rap landscape would be the real fantasy. "Stan"-level crazy, yo.

I made the verrrry, verrrry difficult decision to swap out “The Bridge Is Over” for this one. Truth be told, at least five Boogie Down Productions joints could easily live here—“Love’s Gonna Get’cha (Material Love)” alone plays out, scene by scene, the moral traps so many YBMs in urban America find themselves navigating. But it’s “My Philosophy” that earns the slot, pulled from BDP’s sophomore album and marking a crucial pivot in both KRS-One’s career and rap music itself.

By this point, KRS had already taken heat during BDP’s verbal war with the Juice Crew out of Queensbridge—especially after proclaiming that Roxanne Shanté was only good for steady fuckin’. She was 15 years old at the time. But it was Scott La Rock’s murder in 1987, killed while trying to mediate an unrelated dispute, that truly altered the group’s trajectory. That moment pushed BDP sharply toward socially conscious rap, while the Juice Crew leaned further into slickness, star power, and commercial dominance.

With “My Philosophy,” KRS-One publicly crowned himself rap’s teacher, positioning hip hop as a classroom rather than a battleground. He made it clear he was done using records as vehicles for petty beefs—something that would, unfortunately, evolve into an entire subgenre of rap in the decades to come.

That didn’t mean the disses disappeared. KRS never stopped aiming at sucker MCs—but now the shots served a purpose. His critiques were framed as warnings: stop reinforcing negative stereotypes and start uplifting Black people. And to his credit, KRS-One backed that up across multiple albums, both as the frontman of BDP and later as a solo artist.

Rarely chasing chart placement or crossover appeal, KRS-One infused rap with a level of social consciousness that still echoes today. I doubt it mattered much to him that history crowned BDP the victors of the South Bronx vs. Queensbridge feud. His message operated on a higher plane—one that solidified his status not just as a great MC, but as an elder statesman. A King.

Tragically, Scott La Rock’s death—often cited as the first high-profile rap artist lost to gun violence at the hands of other Black men—opened a door that would never close. Dozens upon dozens would follow. Which makes KRS-One’s 1989 warning that we were “headed for self-destruction” feel less like rhetoric and more like grim prophecy.

I saw a video with DMC talking about when Run-DMC were all the rage, the only other artist that put some fear into them was a young, hungry and talented LL Cool J. They knew how good he was going to be--Run's older brother Russell had just signed him to Def Jam--so they went about their business without ruffling his feathers.

Kool Moe Dee was a respected veteran on the hip hop scene and took personal offense to LL's braggadocio, especially on his "Bigger and Deffer" album. Not sure what he was thinking when he released "How Ya Like Me Now" (both the single and album) as a direct attack on LL, but he definitely poked an angry bear with a very short stick.

You can tell by the relatively groovy, but unsophisticated production value of "How Ya Like Me Now" and its uncomplicated rapping style, that Moe Dee may have slightly miscalculated the more aggressive, lyrically elaborate direction rap was going into by the late 80s. Produced by a very young Teddy Riley (on what sounds like his Casio), "How Ya Like Me Now" feels more like a pleasant stepping stone to the future of rap than a crucial part of it.

This rivalry has always puzzled me. I'm not sure how Moe Dee planned to get the upper hand with rhymes like "I'm no phony, I'm the only real mic-aroni" and with wardrobe choices and dance steps in the video that look like something my dad would do--I'm referring to my dad at his current age of 79. (Back in 1987, Pops could have easily skunked Moe Dee in a cool contest.). There was never a moment that I felt that these two artists were in the same peer group.

Truth be told, "How Ya Like Me Now" is a fine record and is part of the reason Kool Moe Dee had a successful career. The issue here is that it will always be part of a series of beef records that will forever be set next to LL's, like the blistering "Jack the Ripper" and "Break of Dawn" in which he takes on three MC's at once. And Moe Dee comes away looking wildly outmatched, having bitten off quite a bit more than he could chew.

This same dynamic repeated decades later when Drake decided to square up with an absolutely unstoppable Kendrick Lamar. And look—Drake being in diapers during the Moe Dee–LL drama is no excuse. His team could’ve made a quick trip to Brooklyn, flagged down Kool Moe Dee on his mail carrier route, and asked for some desperately needed advice.

Those who do not learn from history are doomed to repeat it, Dray-Dray.

“P.S.K. What Does It Mean?” was a massively influential track—basically one of the early blueprints for what we later started calling gangsta rap. I’ll be real: I was vaguely familiar with the song in the ’80s, but I couldn’t have picked it out of a lineup. Even when Siouxsie and the Banshees incorporated the beat into their “Kiss Them for Me” in 1991, it didn’t click. Biggie even paid homage on "Life After Death", and I still didn’t fully understand why this particular track was treated like sacred scripture.

Another thing I didn’t understand: why nobody, nobody, had pulled me aside and told me how hot Schoolly D was back in the day. I watched a few of his old videos for this entry and—listen—those buns were looking firm, lifted, and ready to serve. The man has an album from 2000 called "Fuck ’N Pussy", but I’m convinced it’s missing a word: "Fuck 'N Boy Pussy" would have been a much funner title.

Schoolly D looked straight-up dangerous back then too—like the type of dude who’d take you behind a middle school before homeroom and get you pregnant. Honestly, at this point I’m starting to wonder if that’s what the P in P.S.K. stood for.

Artists from Sugarhill Records were easy to identify because the records were famously formulaic—but that wasn’t really their fault. Much of the catalog followed the disco-rap format, a style that allowed very little modulation or experimentation. Rapping in unison. Dance- and skate-centric themes. Clean lyrics with a rigid structure. Extended mixes designed to fill an entire side of a 12-inch. The mission was simple: get the record spun at the roller rink, the local club, and radio stations in major markets.

And Funky 4 + 1 worked that formula into the ground—making history in the process. They were a rap group of many firsts: the first rap group to sign a record deal, the first to perform on network television (Saturday Night Live), one of the first groups whose members appeared in hip hop’s first widely released film (Wild Style), and the first commercially successful rap group to include a female member. That last distinction belongs to Sha Rock, though she wasn’t the first woman rapping on wax—the all-lady trio the Sequence had already made waves with “Funk You Up” a year earlier. (Big ups to Angie Stone!)

Built around A Taste of Honey’s “Rescue Me” (Am I the only one who hears in that song's lyrics as “deep inside, it’s got me wantin’ and achin’ / For you to fill me with your cum”?), Funky 4 + 1 wisely avoided any lyrical Freudian slips and instead lifted the beat from the intro. From there, it’s unison rapping all the way—lyrics designed to cold-rock the party that rocks the body. The result is sunny, joyful, and innocent in a way rap would soon grow out of. More importantly, Sha Rock’s presence helped establish, very early on, that rap wasn’t just a man’s game, directly influencing the high court of lady rappers—MC Lyte, Queen Latifah, and Roxanne Shanté among them. Now, THAT'S the joint!

P.S. One member of Funky 4 + 1 went by the name MC Jazzy Jeff (Jeffrey Miree). After the group disbanded, he signed with Jive Records and recorded an album in 1987. That same year—coincidentally—Jive also signed a duo from Philly called DJ Jazzy Jeff & the Fresh Prince. Between 1987 and 1988, the duo released the gold "Rock the House" and the triple-platinum breakthrough "He’s the DJ, I’m the Rapper," while the record company Jive turkeys never let Miree’s album see the light of day.

In 1994, Jeffrey Miree sued Jeffrey Townes (DJ Jazzy Jeff) and Jive’s parent company Zomba Records, alleging trademark infringement and seeking $30 million in damages. Miree ultimately won legal ownership of the name “Jazzy Jeff.” Despite that judgment being in Miree’s favor, DJ Jazzy Jeff continued to work and release music under his stage name. There’s no clear public record of any payout to Miree, but one can only hope that whatever compensation—if any—came his way was sweet like a taste of honey, and not a Big Willie Style slap in the face.

I give Queen Latifah a lot of grief throughout this blog, but it’s always done in good fun and with zero ill will toward the Queen. Truth be told, my Latifah knowledge is a bit limited: I really only know this classic feminist jam and the Grammy-winning “U.N.I.T.Y.,” plus the occasional glimpse of her acting career. (My dad is a devoted "Equalizer" fan. I’ve tried to watch it multiple times, but it comes on at the ungodly hour of 9 p.m., and I inevitably pass out like the old-ass queen I am.)

I don’t actually have beef with Queen Lateef. The only time I ever side-eyed her was when she wasn’t being straight up—no pun intended—about her sexuality, back when everybody already knew she liked to licky boom boom down.

That said, alongside Sha Rock, MC Lyte, Roxanne Shanté, and Salt-N-Pepa, Latifah is a certified pioneer. Songs like “Ladies First” didn’t just make a statement—they helped clear the runway for Da Brat’s Funkdafied to go platinum five years later, while also opening doors for artists like Lauryn Hill and even Lil’ Kim to rise to the top. Latifah also played a key role in launching British rapper Monie Love’s career and even survived a very public feud with Foxy Brown. (Yes, Foxy is the better rapper—but there was no universe in which she was going to win in the court of public opinion. Granny’s fried chicken might be the best on the block, but it’s still not beating the Colonel when face recognition and brand goodwill enter the chat.)

Outside of this song, I may not know Latifah’s catalog deeply, but I like her—and I love what she represents. I love Black lesbians in show business, so when I throw shade at the Queen, it’s only because I’m a shady queen my damn self. Full stop.

And if I have any lingering issue, it’s really with Simone Johnson, aka Monie Love, who single-handedly set educational progress back several years by spelling “lady” L-A-D-I-E in the song. Aren’t Brits supposed to be smarter than us? Latifah did tell her to "grab the mic and get dumb," so I guess she was just following the Queen's wishes, like a good Brit should.

Every time I hear that line of yours, Ms. Johnson, it fills me with a quiet but persistent sense of acrimony, love.

1994 was one of those undeniable high-water marks in rap history—the kind of year people still argue about in barbershops and comment sections. "Illmatic", "Ready to Die", "Ill Communication", "Hard to Earn"… the hits kept coming, and collectively they yanked the hip-hop pendulum back toward the East Coast with real force. I was lucky enough to have moved to New York City the year before, so I got to feel that paradigm shift up close and personal. While Jeru the Damaja doesn’t get mentioned in the same breath as Biggie, Nas, or even Guru, he contributed mightily to that grittier, more urban strain of rap—music the kids in Des Moines weren’t quite ready for yet.

“D. Original” sounds ominous enough to have slid right into a Twilight Zone soundtrack—if such a thing had existed back then. Built on a clever sample of Guru’s vocals from “We Write the Songs” and anchored by an eerie piano figure lifted from free-jazz madman Cecil Taylor, this is DJ Premier operating at full genius. The track feels truly singular, unlike almost anything else getting radio play at the time, thanks to Premier’s bottomless crate-digging instincts and his unmatched sense of mood. The beat alone announces itself as different—cold, stripped, and confrontational.

Jeru may not be the most charismatic MC in the boroughs, but he’s focused, sharp, and perfectly suited to this atmosphere. He rides the beat with authority, making “D. Original” one of the standout singles in a year overflowing with classics. The scratching, the dusty textures, the matte, no-frills production—this is exactly why DJ Premier remains the premier DJ-producer in hip-hop history.

Jeru is a fine lyricist, though I do have a lingering concern about his spelling. (Damaja? Really, tho?) I once spent a very brief stint teaching middle school in his hometown of East New York, Brooklyn, and I can say with confidence that Jeru came a whole lot closer to the correct spelling of “damager” than most of the kids in my classroom. In that sense, at least, the name checks out.

Black Sheep were part of the early-’90s Native Tongues consortium, a whole movement of creative rap nerds who entered hip hop like a puff of fresh incense smoke—jazzy, Afrocentric, inventive, and fully committed to raising the collective IQ of the genre. The Native Tongues roster was wild: De La Soul, A Tribe Called Quest, Jungle Brothers, Queen Latifah…basically the Avengers for backpack rap. Black Sheep fit right in.

Their breakout, “The Choice Is Yours (Revisited),” comes flying in with jazz-infused beats and that signature cerebral style that invited immediate comparisons to Tribe (not hurt by the fact that Q-Tip had production credits on their debut). Before the world at large knew who they were, Dres and Mista Lawnge had already made noise as guests on De La Soul’s debut and became the first rap act to ever perform on the freshly rebooted Tonight Show with Jay Leno. Things were looking promising.

The magic of the song lives in the hook: “You can get with this, or you can get with that.” It’s catchy, it’s rhythmic, it’s practically a philosophy class in the art of choosing vibes. The beat is tough, anchored by a jazz bass sample from Johnny Hammond Smith’s “Big Sur Suite,” and Dres absolutely tears through it with a confident, elastic delivery that made him the duo’s MVP. He later popped up as a guest on projects by artists like Nas after Black Sheep went on hiatus.

Though their debut album is still considered a gem among hip-hop heads, “creative differences” (rap’s favorite breakup euphemism) split the group by 1995. They’ve reunited here and there over the years, but this single remains the moment when everything aligned.

"The Choice is Yours (Revisited)" stands as the group's stellar moment, though they may also be known for Mista Lawnge's loaf of bread haircut on album cover, a style so daring that even the sheep on the album cover turned and did a double take.

We can now confirm that when it came to Diddy, it really was all about the Benjamins. And the Tyrones. And the Marcuses, too. (And didn't Puff rap that he had to get his hands on some Grants like Horace? Little did we know that he wasn't speaking metaphorically.)

“So many baby-oilable boys out there, so little time,” Puff must’ve been thinking back when he ruled New York City with a shiny fist and a camera always rolling.

I was a staunch East Coast rap loyalist, but when the burly Death Row CEO stomped onto the Source Awards stage and called Combs out for being all up in everybody’s songs and videos, I had to nod along and mutter, “Shug Avery sho’ ’nuff make a good point there. Yes he do.”

There’s always been something deeply unlikable about Puff—so much so that he somehow managed to make me root for J.Lo in their love saga, and she herself is about as likable as the Hillside Strangler.

Still, you cannot deny the magic of “It’s All About the Benjamins,” a rap Voltron that somehow had something for the whole family. The L.O.X. show up for your smooth-thug older brother. Biggie isn’t at his lyrical peak, but he holds it down for the rap purists. And if you prefer your bars endorsed by Hasbro, Puffy swoops in with rhymes so juvenile you’d swear they were coded on an Atari. Then there’s Kim, floating in with her “wanna bumble with the bee, huh? Bzz—throw a hex on the whole family,” sending the banjee queens like me into full bounce mode at the club. No matter how you felt about Puffy, "It's All About the Benjamins" rocked whatever event you were attending at the time.

By this point, Puff had reached full Madonna-levels of self-promotion. Even as a proud, card-carrying playa hater, I’ll be damned if I didn’t own a knockoff Sean John hoodie scooped up from a kindly Chinese vendor on Canal Street. His presence—and power—loomed over New York in the ’90s, and “Benjamins” was one of those records that cemented his reign, blasting out of every car from Inwood all the way to Far Rockaway.

Like him or not—and most of us didn’t—Puff had the city on lock. And for a minute there, even the dead presidents had to sit up in their graves and pay attention, even Benjamin Franklin who, though dead, was never a president.

At first, I found the Wu-Tang Clan to be a bit disorienting. There were just too damned many of them. They all had overlapping aliases, and the music was full of kung fu philosophy I wasn't tryna understand at the time. And I think I used to confuse them with the Ying Yang Twins, so it took me a minute to get my bearings. Luckily, Method Man was the lighthouse in the fog. He kept popping up on other people’s songs — most notably on Biggie’s “The What?” and whatever random Redman joints drifted across my speakers — and he served as the Clan’s unofficial ambassador to the mainstream.

He does it again here, only this time he stays in the family on fellow Wu cousin GZA’s sophomore album, "Liquid Swords". Produced by the RZA, the record features some of the best Wu material outside of the group’s debut. The Wu-Tang Clan was like a Staten Island octopus: if you only followed the main group albums, you missed four or five other arms flailing wildly and brilliantly. Early solo joints by the GZA, Raekwon, Method Man, and the RZA himself sit just underneath "Enter the Wu-Tang (36 Chambers)" in terms of quality and influence.

On “Shadowboxin’,” Method Man comes in sounding half-asleep, which — somehow — works perfectly. Johnny Blaze slides in behind that syrupy Ann Peebles sample (“Trouble, Heartaches and Sadness”) while RZA hacks up the drums into something smoky, woozy, and cinematic. The track feels like being in a dark room full of incense, VHS tapes of Shaw Brothers films, and grown Black men nerding out over mythology and martial arts like they’re at Comic Con comparing Star Wars action figure variants.

Wu-Tang is hip-hop at its nerdiest and coolest. And it was “Shadowboxin’” that finally helped me understand that — it wasn’t about getting every reference, it was about surrendering to the atmosphere. Once you do that, the smoke clears.

Heavy D's weight wasn’t all that heavy when he hit the scene—certainly not compared to the Fat Boys, Big Pun, or even Busta Rhymes at his fattest. But when it came to popularity across Black urban music audiences, Hev was about as big as it got. Call it clean rap, adult contemporary rap, or whatever label makes critics comfortable—what everyone can agree on is that Heavy D made some of the catchiest, most danceable rap records of his era.

Here’s what that kind of appeal really looked like: my oldest brother couldn’t stand rap back in the day, but he loved him some Heavy D.

This was that juicy period in hip-hop when the goal wasn’t just to rip clever rhymes, but to get more bodies on the dance floor. Heavy never lost sight of that foundation, approaching rap with an openly pop sensibility—and succeeding wildly because of it. For me, it all kicked off with “Mr. Big Stuff,” a joint that rocked the Black Teen Dance and lived permanently in my cassette player as I rolled around in my Suzuki Samurai.

When you’ve got young, hungry power players like Andre Harrell, DJ Eddie F, Marley Marl, Al B. Sure!, and Teddy Riley in your corner, superstardom is almost inevitable. And Heavy D earned every inch of it. The beats were right, the rhymes were sharp, and the Boyz managed to blend old-school sensibilities with contemporary street trends without offending a single soul. It didn’t hurt that they were all adorable and smiley either, making “Mr. Big Stuff” practically impossible to resist.

Industry folks have always said Heavy D was one of the nicest dudes in the game. I can’t confirm all that—but I can tell you this: I once pulled up next to his SUV on Worth Street in Lower Manhattan while riding my bike. I didn’t even realize who he was at first. The window was down, I said hello, and he hit me back with the warmest “wassup, G,” smiling like we went way back.

That moment stuck with me.

His unexpected passing in 2011 was a tremendous loss—to hip-hop, to Black music, and to the world. Wherever you are now, Hev, we’re still wishing you a Peaceful Journey.

By most accounts, O.D.B. was just as outlandish off-screen as he appeared on it. Drunk. Drugged out. Unruly. Annoying. Entertaining. And, allegedly, unbathed.

He was infamous for skipping scheduled engagements only to randomly pop up at places where he absolutely was not invited. Judging by the video for this song, it seems O.D.B. forgot to add the shoot to his Google Calendar and had to be edited into the scenes after the fact. Fortunately, Kelis showed up—both for the vocal session and the video—and her contributions are perfectly placed on this Neptunes-backed jam. (“Got Your Money” marked Kelis’ first appearance on wax; her debut album would drop just a month later.)

On the record, Dirty rambles about this, that, and whatever else crosses his mind, leaning fully into the erratic, free-associative rap style that made him absolutely singular. Reeling him in for a mainstream track could not have been easy. O.D.B. was notorious for spitting a stanza or two and then taking an extremely long nap. His on-record demands for money weren’t just performance art either—they mirrored real life. Dirty often insisted on being paid up front, sometimes requesting clothes and liquor as part of the deal. He’d spit a few bars, kick off his shoes, pass out, wake up, demand more money, record a few more lines, then fall back asleep—leaving producers to Frankenstein the takes into something coherent. (Reportedly, the shoe-kicking-off part was the most traumatic aspect of the whole ordeal as his feet were funkdafied.)

Why did producers tolerate such tomfoolery? Because the end product was almost always irresistible. “Got Your Money” is proof.

Grammy-nominated—yes, Grammy-nominated!—rapper O.D.B. was bigger than music. So big, in fact, that he altered public policy. When he famously cashed a welfare check and picked up food stamps while his album sat comfortably in the U.S. Top 10, the resulting backlash led to sweeping changes in the social welfare system beginning in 1996.

He didn’t make it to 36 years old, but what he left behind—both the music and the stories—will keep us entertained, baffled, and bobbing our heads for years to come.

I loved EPMD’s first two albums back in high school, but I was never quite sure how seriously I was supposed to take their lethargic, slurry rap style. “You Gots To Chill,” “Knick Knack Patty Wack,” and “It’s My Thing” were party records, sure—but they had just enough grit and street edge to keep urban audiences from writing them off as novelty rap.

Record label drama, money problems, and internal friction eventually derailed the duo, who have been on-again, off-again for decades. Still, Erick Sermon managed to forge a legendary second act as a producer, establishing himself as one of the true pioneers of the sampling era.

“Music” became Sermon’s signature hit for Clive Davis’ J Records, and it plays like a heartfelt tribute to Marvin Gaye, who is unmistakably the star of the show. Built largely around a sample of “Turn On Some Music” from Gaye’s triumphant comeback album "Midnight Love", the track also features additional Marvin vocals not heard on the original recording. Sermon has said he stumbled upon these unreleased snippets while crate-digging in a small London record shop. However it happened, the result was magic.

The single became a major success and a career high-water mark for Sermon—ultimately the biggest hit of his career across all incarnations, whether with EPMD, Def Squad, or as a solo artist.

Unfortunately, momentum stalled after a series of serious health setbacks. In 2001, Sermon fell from a third-floor window, and a decade later, in 2011, he suffered a heart attack. While those incidents slowed his output, they did little to diminish his legacy. Erick Sermon remains a foundational figure in hip-hop history—proof that even a deceptively laid-back delivery can leave an outsized impact.

Black Moon is another one of Brooklyn’s own who got their start in Bushwick High School, back when Bushwick wasn’t the place you went for a $16 wheatgrass smoothie after an hour-long restorative yoga session. Before the art galleries and oat-milk cortados arrived, Bushwick gave us rappers who sounded like they recorded their verses in the basement of a bodega after the cat went home for the night.

“I Got Cha Opin” is best heard in its original album incarnation — jazzy, murky, and decidedly grimier than the Barry White–laced remix that powered the music video and got radio love. That remix is cute, but the album version flexes that muddy, street-level sound favored by Wu-Tang and Mobb Deep: bass like a wet floor and snares that seem to echo off abandoned warehouse walls.

It’s also a little sonic detour from their breakthrough single “Who Got Da Props,” which was jumpier, more Native Tongues in spirit, with the call-and-response chorus and bouncier beat. “Props” likely earned the duo the most… well, props, but “Opin” feels more raw and unvarnished — impressive for a squad who were barely old enough to legally buy a pack of Newports at the time.

Meanwhile, Buckshot had a business brain to go with the bars. At just 18, the man formed his own label and production house, Duck Down Entaprizez, managing Smif-N-Wessun and Heltah Skeltah and later getting involved in projects involving names like Aaliyah and even 2Pac. Bushwick may have looked rough, but the ambitions were always sky-high.

The creative spelling choices also serve as historical markers of that hardscrabble era. I get writing “enta da” instead of “enter the” — that’s branding — but was it necessary to spell it “opin”? And don’t even get me started on “Entaprizez,” which sounds like what a second grader writes on a business plan for their lemonade stand.

Their album was called "Make It Reign", but I was never convinced that Lord Tariq and Peter Gunz were going to make any real dent in hip-hop beyond their inaugural monster hit. The moment I saw the video, I clocked them as Kid ’n Play 2.0—curse words included—just without the movie franchise. Still, credit where it’s due: you simply can’t go wrong with a Steely Dan sample, which turns out to be the real star of the song. That bouncy bass line and those slick keyboard touches are lifted straight from the intro of “Black Cow,” seemingly right out of the can, with no detectable embellishments added to the loop.

The co-stars of the track are its two hooks, starting with “New York dudes got crazy game,” and carrying the record’s energy as much as the beat itself. While the duo bigs up the Bronx’s role in birthing hip-hop, the song ultimately plays like a love letter to all four of New York’s important boroughs, with sprinkling a little love tossed on Staten Island, Westchester, and Long Island. Even with the East Coast–West Coast foolishness in full swing at the time, I never felt much Uptown–Brooklyn rivalry back then. That said, those of us who dwelled in Brooklyn probably walked with a little extra swag, knowing we were being represented heavy by Biggie and his crew.

So when this record blasted through the speakers at the gay Black club up in the Bronx, you could feel the pride in the room as all the boys chanted the second hook—“Uptown, baby! Uptown, baby! We gets down, baby! For the crown, baby!”—with absolute fervor. “Déjà Vu (Uptown Baby)” gave Bronx queens a second reason—beyond the Yankees—to throw their Roleys in the sky and wave them side to side. Beyond those two things, though, we really couldn’t be bothered with the Bronx. Why y’all think folks been trying to burn it down for the last fifty years?

Tatyana Ali later used the same Steely Dan sample for her 1998 hit “Daydreamin’,” even inviting Tariq and Gunz to spit some uncredited rhymes on the track. (She wisely passed on the Jerry Rivera sample that opens their original song.) For years, we assumed Peter Gunz was talking about his pistol—but the six-shooter he got the most mileage out of was his dick, fathering ten children, including rapper Cory Gunz. Cory’s mentor, of course, is Nick Cannon, a man who used his own cannon to place twelve additional humans on the planet.

Hip-hop math be wild sometimes.

Diddy opens the remix playfully crooning, “Baaaad Boy… come out and plaaayy.”
I’d advise against that.

Once Puffy realized exactly what he had with the original version of “Flava in Ya Ear,” he immediately ordered up a remix and stacked it with names far bigger than Craig Mack’s, effectively forcing Craig to play second fiddle on his own damn record. Biggie was invited and absolutely tore it down. LL Still-Cute J showed up, Busta—back before he evolved from Busta Rhymes into Busta Seam-In-Ya-Jeans—set it ablaze, and guest-rapper-for-hire Rampage somehow got tossed into the mix too.

This moment marked the real beginning of Bad Boy Records, and it didn’t take long for Craig Mack to become the label’s first disgruntled employee. The experience with Puffy reportedly traumatized him so badly that he eventually fled into the warm, waiting arms of a religious cult leader.

Craig wasn’t just overshadowed—he was neglected, mistreated, and never properly compensated. And with three of the hottest rappers in the game dominating the most popular version of his signature song, how the hell was he supposed to perform his biggest hit live? Craig faded almost as quickly as he arrived.

He tried to mount a comeback, but few were listening when his 1997 follow-up "Operation: Get Down" dropped. The lead single sounded like a pale carbon copy of “Flava in Ya Ear,” only without any of the fun or flava supplied by Easy Mo Be, Busta, or the recently deceased Biggie. Critics and fans alike weren’t kind, handing the project a collective grade of an Easy Mo D-minus, effectively sealing the end of Craig Mack’s moment in the spotlight.

Craig Mack died in 2018 at just 47 years old after complications from untreated HIV/AIDS. His legacy is bittersweet: the voice that launched a rap empire, then got buried beneath it.

Errbody and they auntie had a hit single in 1994. Ill Al Skratch brought together Brooklyn’s Big Ill and Harlem’s Al Skratch—two dudes I hadn’t heard of hitherto. Their second single, “I’ll Take Her,” paired the duo with R&B’s lethal dose of NyQuil, Brian McKnight, and somehow the combination produced something kinda special. Without claiming deep knowledge of McKnight’s catalog, I can say with full confidence that “I’ll Take Her” is his finest moment on record. Ill Al Skratch may very well have better songs buried in their discography, but who has the time—or the patience—to find out for sure?

The most interesting thing about the track is its use of Curtis Mayfield’s “You’re So Good to Me,” the same sample Mary J. Blige flipped on “Be Happy.” Both records dropped around the same time, which makes you wonder whether the respective labels knew what the other was cooking. If this was supposed to be a head-to-head showdown, though, it wasn’t much of a contest—Mary absolutely mopped the floor with both Ill and Al.

Still, that doesn’t mean “I’ll Take Her” can’t stand on its own two feet. It’s a solid mid-’90s jam, smooth enough for the radio, street enough not to feel corny, and anchored by McKnight’s syrupy croon doing most of the heavy lifting.

Ill Al Skratch—not to be confused with Kurtis Blow’s DJ AJ Scratch or Paula Abdul’s animated homeboy MC Skat Kat—had already notched a surprise hit earlier that year with “Where My Homiez? (Come Around My Way).” For a brief moment, that was enough to keep them in the conversation. Like many acts of the era, though, they ended up as a footnote in a year overflowing with classics, casualties, and one-hit wonders that all seemed to arrive at once.

No matter how popular “Wild Thang” had been, nobody expected Tone Lōc—who already had one foot planted firmly in the Novelty Rap bucket—to get past one-hit-wonder status. Then “Funky Cold Medina,” the second single from his debut album and his third single overall, went platinum and climbed to No. 3 on the pop charts, landing just one slot behind “Wild Thang” itself.

Both songs were written by Young MC (Marvin Young), both are gimmicky as phuck, and both are undeniable pop gold. That said, “Wild Thang” never quite hit me as hard as “Medina.” There’s something about that little stutter-step beat that grabs my attention—once again, me falling in love with some minuscule detail most listeners probably never clocked.

While mainstream media outlets were clutching pearls over the dangers of gangsta rap corrupting Des Moines pre-teens, a whole other consortium was quietly assembling a brand of rap that could air comfortably on both MTV and PBS. Heavy D., MC Hammer, and Tone Lōc weren’t interested in social upheaval or bitches-and-hoes narratives. They just wanted to make your body feel good—with a groovy beat and a few G-rated rhymes that wouldn’t summon the wrath of Jerry Falwell and them.

“Funky Cold Medina” isn’t meant to be taken seriously. It represents that slim slice of rap that was poppy, goofy, fun—and highly marketable.

With his Darth-Vader-on-quaaludes drawl, powered by Young MC’s pen, Lōc tells a story plenty of men could relate to at the time: if your broke ass is too fat and ugly to get laid unassisted, why not slip the girl a mickey? Funky Cold Medina—like Spanish Fly before it—won’t earn you marriage proposals or increase the number of dogs doing the wild thang on your leg, but it’s a ridiculous enough premise to hang a song on. It’s a fictional aphrodisiac, the same type of mythical potion Flavor Flav loved hollering about in Public Enemy records.

Tone Lōc even slips some Medina to a cross-dresser named Sheena. Things are going great—until he takes her back to the house. That’s when the night devolves into a big ol’ mess once she gets undressed. The confusion, apparently, stems from Lōc’s inability to distinguish a transgender woman from a cisgender one—an issue many straight men of that era dealt with, I suppose.

At the end of the day, it’s hard to get truly mad at Tone Lōc for the gender insensitivity, because it was all clearly done in the spirit of cartoonish fun. Nobody expected Tone and his music to reunify North and South Korea or solve the JonBenét Ramsey case. The goal was simply to goof around for a few minutes without anybody getting hurt.

And for that brief window of time, Tone Lōc and Young MC pulled it off splendidly.

The best songs often spring from real-life events — the stuff you see out your window, hear on your block, or duck behind a car to avoid — which gives music that irreplaceable whiff of authenticity. Rock Master Scott & the Dynamic Three were from the Bronx, so when they declared that the roof was on fire, they were not speaking metaphorically. That borough had more burning buildings than a Godzilla movie.

By 1984, rap was slowly pulling itself out of the disco-rap era and, led by Run-D.M.C.’s debut, edging into a harder, more serious mode — rapping about real life over skeletal drum-machine skeletons. But before all that gravitas arrived, we had joints like “The Roof Is On Fire,” records made to amp up the party, not shoot it up. There was humor, there was bragging, there was joy. “You got on clean underwear and your mama ain’t on welfare — say yeah!” is not exactly Kendrick Lamar, but it did its job.

This was also the golden moment when Black artists finally got their hands on high-quality drum machines and decided to program those suckas until they started to smoke. “The Roof Is On Fire” features a little scratching and cutting to spice things up, but the dominant force here is that drum machine, which sounds like it blew a fuse in the studio. Rock Master Scott clearly wanted the song to function as party infrastructure — lots of call-and-response (“I like it! I love it!”) and a chorus that would be shouted at roller rinks, block parties, and suburban basements for the next forty years.

And it wasn’t just club kids who took notice. New York politicians gazed out their windows, saw the Bronx engulfed in flames yet again, and gleefully joined in on reciting Rock Master Scott’s timeless instructions: “We don’t need no water, let the muthafucka burn! Burn, muthafucka, buuuurn!”

And crucially, Rock Master Scott & the Dynamic Three were no one-hit-wonder novelty act. They also blessed the culture with “Request Line,” a legitimately enduring record that’s been sampled repeatedly over the decades — including by Missy Elliott, who put it to excellent use on “Work It.” When it comes to hip-hop party anthems, their roof wasn’t the only thing on fire.

“Ms. Jackson” was written with Erykah Badu’s mother in mind — a woman who surely must be thrilled that her daughter is a legend, but maybe not so giddy about having three grandchildren with three different baby daddies and zero son-in-laws. (The roster: André 3000, The D.O.C., and Jay Electronica, in that order.)

André 3000, the cutest member of Outkast by a comfortable margin, showed up for the role with charisma for days, washboard abs, and the kind of eclectic glam that lets you wear a dress on your album cover without breaking into a single explanatory monologue. He was one of the best things to come out of the South since deep-frying everything. And honestly, nobody should have been surprised when he wandered off years later to record a solo album of flute music — that’s just what we Funny Blacks do.

But Badu didn’t need to marry a single one of these men because that woman came prepared with her own economic stimulus package. Besides being a legendary performer, she’s a businesswoman with multiple revenue streams: cannabis-based products, clothing, and a line of incense so powerful she reportedly had hotels on backorder. One scent she christened “Badu Pussy,” presumably after discovering that “Tuna Helper” had already been trademarked by Betty Crocker.

“Ms. Jackson” remains one of Outkast’s most beloved singles and one of the first major cultural texts to acknowledge the struggles of baby mama diplomacy with both humor and tenderness. It’s an apology song for the ages — and considering all involved parties are still alive, thriving, and occasionally releasing extremely weird art, it worked out for everybody in the end.

(I wonder what Erykah's return policy is on that Badu Pussy incense...)

I’m generally not a fan of anthemic rap songs that set out to force a sing-along, the kind that treat the listener like a second grader at an anti-drug assembly. I’m looking at you, Naughty By Nature’s contrived “Hip Hop Hooray,” and definitely you, “Boom! Shake the Room,” Will Smith’s fully decayed take on House of Pain’s “Shamrocks and Shenanigans (Boom Shalock Lock Boom).” But “Slam” was different.

Onyx came in like they had been raised by wolves and given a two-liter of Jolt Cola for dinner. Led by the charismatic and on-the-way-to-sexy-but-not-quite-there Fredro Starr, “Slam” burst out of the speakers with so much unbridled energy you had to stop what you were doing to pay attention. The hook leans heavily on The Mohawks’ “The Champ,” one of rap’s most sampled psyche-soul cuts. But instead of sampling it, Onyx vocalized the melody like a gang of fevered gym class delinquents — arguably more chaotic and definitely more fun.

The song also attempted to bring slam dancing into hip hop, which was exactly the thing the genre needed, just like a hole in the head. But you couldn’t deny that “Slam” tapped into a raw adolescent adrenaline. It was instantly recognizable and easily deployable for anything involving high expenditures of energy — action movies, sports montages, and TV shows that just needed something loud to cover the fact that the plot wasn’t plotting. It’s landed on many lists over the years, including one of my all-time favorites: Complex’s 25 Rap Songs That Make Us Want To Punch Someone in the Face.

The success of “Slam” also arrived at just the right moment. Def Jam Records wasn’t exactly thriving in the early 90s, and Jam Master Jay’s signing of Onyx to his JMJ imprint became one of the swings that helped keep the lights on. It didn’t hurt that Onyx came off like the scariest kids on the jungle gym — that always sells.

Fredro Starr probably learned the hard way that rapping this hard and this frenetically wasn’t sustainable over the long haul (just ask Busta Rhymes’ pulmonary system), but for one glorious moment, Onyx sounded like they were about to kick down your apartment door and demand some purple drink.

OK, this was not launched as a single, but I had to include it here as it's the song that launched Nas. We all know and love "Looking at the Front Door", but there is something sublime about "BBQ"

Still sexy daddy Large Professor

"Breaking Atoms" as a landmark album

I absolutely love Black Nerds

The D.O.C. was going to be the West Coast's next big thing just a few months before a near-fatal car crash nearly took his voice and several years before being #2 on Erykah Badu's baby daddy registry.

Ya'll remember the whole Gay Rapper hype in the 90s amplified by NY big mouth Wendy Williams? There was talk that it was Puffy, Missy, LL and Erick Sermon. Q-Tip's name was also floated around mainly because he was too cute to be straight.
Video by Hype Williams
Nice Barry White sample
"Breathe and Stop" sounds like good advice for bottoms looking to take big Jamaican dick in the bum

Jill Scott wrote the hook but Erykah Badu sang it.

I constantly talk about Philly but I don't think I've ever been there. There's something organic about music that comes from there and that's a perfect word to describe The Roots.

Eve raps but doesn't get any real credit.

Of course, we had no idea that the hook was lifted from a Nobody Beats the Wiz commercial since we had never heard of such a place out in Cowbell County, Arizona.

TJ Swann was not going to win the Teddy Pendergrass Award for Vocal Performance in a Rap Song, but I think his off-key singing was supposed to be part of the fun that surrounded Biz, a guy that many thought was on the spectrum before he made it big.

Marley Marl was a production genius of raps first heyday.

"Fly Like an Eagle" Steve Miller Band

So many people thought 2000 was going to bring some type of judgment. Hell, even I moved out of the U.S. that year and went to live under a coconut tree in Colombia to avoid the impending "armagiddeon"

I'm cheating here because "Dangerous Grounds" was not a single from Method's great, but skit-heavy album

DMX's debut album came jam-packed with classic like "Get At Me Dog"

Rap music in and of itself is an exercise in hyperbole as most of what dudes rapped about was just hype.
But there was something sincere and authentic in DMX, an artist who brimmed over with the anger and angst of yet another Black man mistreated by society and possibly the ones he trusted.

"Party Up" could have also made this list but maybe the way DMX looked at tasty like a handful of Kit Kats in this video gave it the edge.

If you were blessed enough to be Black, gay and living in NYC during the 1990s, then you already know what the tremendous power this song had on us when it came blasting through the speakers. (I guess straight people might have also rocked to this jam, but no one's really interested in what those folks do on their free time.)

The star here is the banging sample of "Cavern" by Liquid Liquid.

Why repeat "don't" in the title? Don't two negatives make a positive, meaning that Melle's message is for us to in fact do white lines?

Might have let the hot comb get away from him a bit, but I appreciate the anti-drug message here.

"Err-rah!" (Who did it first? Was it Stevie Wonder on "Ain't Gonna Stand for It?"

Ever got to drunk at an event, made a fool of yourself, woke up the next day and tried to forget the whole thing? That must be how the Beasties feel about their "Licensed to Ill" era, a time that produced the best-selling rap album at the time, but also created personas that did not reflect the men as artists nor the directions they would take their music.

"Paul Revere" is not the group's best single, but it's perhaps their most iconic.

On the cover, Marley is commandeering a yacht, decked out in a captain's uniform and a big gold chain. But on the real, he admits that "I was still living in the projects. I was paying like $110 a month for my rent, free electricity. So New York City Housing Authority kind of co-produced some of my earlier hits".

Kool G Rap, the genres most underrated MC, turns in a tight performance, but had zero charisma on camera, in contrast to very photogenic Big Daddy Kane, who refused to play along with the wild, wild west motif of the video.

Best thing NYCHA ever did for Black folks, ever.

This song ain't got a thang if it ain't got that Nate. Do-rap do-rap do-rap!

Warren G gets top billing because he's got a lot of cute boyish charm, but he's gets outshined by both Michael McDonald's keyboards and Nate Dogg, who turns out to be the Urkel of this family matter. He probably wasn't meant to steal the show, but that's exactly what he did with his melodic interjections that are boy soulful and cheeky at the same time.

None of these rap conglomerations every stick. Where is Native Tongue or the Firm these days? Or the Dungeon Family, where dey at? It's easier to signal that the closure of Junior M.A.F.I.A. was solidified with the success of standout artist Lil Kim and the death of Notorious BIG. Who else was in the group? Lil Caesar's Pizza and others. Though he spells it Ceaser with an 'e' to avoid confusion with the Roman Emperor Julius.

Nice use of the sample

Great album title because ain't nothing on earth that makes me more ill than some na na.

Blacks and Asians need to heal our wounds and come together. We have so much in common, like Chinese food and Wu-Tang Clan.

I'm only interested in the boy na na of those cute little background dancers in the video, Fox.

I seem to remember reading somewhere that The Game and his discoverer 50 Cent were beefing with each other at some point. The only beef I'm interested in is the one The Game was showing off in one of his bathroom, hard-on selfies. Though not a bottom and I hate the idea of penis in my mouth, I'm willing to play The Game.

Was it a lover's spat? Bad move, Fiddy. You're not gonna get better than The Game; you were hanging upside down during the Super Bowl performance hoping the magic of gravity would pull all those extra pounds out of eyesight, but physics don't work like that.

You're not going to get any complaints outta me whenever someone decides to sample Steely Dan.

I really wanted to include "Champion" here, but it wasn't released officially as a single, but back in those days, artists released the entire album as singles so I was just gonna pretend that that's what happened here. But then I decided that "Gold Digger" is a more deserving entry for several reasons. The first being that the song kicks some serious bootay.

Danceable rap allowed me to feel a little hard among my white friends because I could do the Running Man. Meanwhile, all the Black guys thought I was more akin to DJ E-Z Bake Oven. But that's alright. All them dudes are obese, dependent on SNAP and got 12 grandkids while I'm still fly as I wanna be. (

I have no idea how we got this in Salamander County, Arizona, but we had the 12-inch single of "The Show" with "La Di Da Di" and I played this record until my wrecka playah filed a formal complaint with my parents

Yes, Kane ghost-wrote the lyrics, but it was Shanté's job to deliver them with precision and pinache. And she pulled it off.

Crossed paths with a very young and very introspective Nas.

Blessed with a once-in-a-lifetime combination of good looks, abs and several freight trains full of charisma, 2Pac never blew me away musically. He had a strong, husky voice and her themes were contemporary, but the music didn't seem to stand as highly when not accompanied by a video.

2Pac was an exaggerated personality, but one thing was for sure: all eyez were on him. Some were filled with love and admiration. Other eyez were murderous.

'Memba how cute Lil Kim used to be? She had no time for fake niggaz, but plenty of time for fake everything else.

Just as I wanted to be Jody Watley ten years before Lil Kim dropped her debut album, I would see in the gay black clubs that the New Jills wanted to be Kim, reciting her lyrics word-for-word and matching a fur coat with a thong all up in the club.

Standing on the littered tracks of what looks like a Brooklyn stop on the LIRR on the album cover, Guru and DJ Premier carved out one of the most enjoyable discographies that I don't feel gets mentioned enough. Like Frito Lays, It was not easy for me to just pick one.

A song that came out in the sweet spot when rap was beginning to allow for divergent points of view and styles, even expressions bordering on the gimmicky. It's sometimes nice to see Black men not take everything, including themselves, so damned seriously.

The late

The deserved Hall-of-Famer Missy dropped a few pounds and brought her unique flavor of rap even closer to the mainstream without losing any of its quirkiness.

I recently moved to a small town in Mexico and have spent about 55% of the time shitting. Remember when they told you to drink flat Coca-Cola for an upset stomach? now I know why Mexicans drink so much Coke.

I like that little knee-lift dance they do throughout the video

Literally too many hot singles to choose from in this late-90s era.

Even in a place that's weak like Arizona or bleak like Memphis (bleak)

Not his best single or song, I know, but taking a song from Annie and taking it hip hop deserves a shout.

Still mad at EPMD making the pre-internet me believe that Long Island was the same as NYC

Cute-Tip and the gang brought the fie-yah with "Check the Rhime" and the entire album.

I don't like Fat Joe. Nothing against fat folks or folks named Joe. Just him. He's annoying.

That said, this was one of those jams that rocked the club that Christmas in spent in DC back in 2004. Next to Santy Claus, Joe was the coolest fat dude in town back then.

So reflective them brothers are on the album cover.

Damn, this is a good song.

Funny Blacks for sure.

This song can't really be considered old skool because it's still relatively new, but I added it here mostly because it's produced by Scoop DeVille, one of my favorite stage names. (He's also the son of hip hop old skooler Kid Frost.)

This came out long before Drake took Kendrick to Judge Judy for publicly hurting his feelings

By the laws of association, if you like "Top Billin'", you must also like "10% Dis."

I wish I could add more women to this list, but I couldn't add Monie Love with a good conscious because she spelled lady "L-A-D-I-E" in her song with Queen Latifah, setting back gains made in urban education a full seven years. And speaking of Latifah, I wasn't able to add her because I needed more LADY ladies on here. I might have questioned adding Lyte here too for the same reason if "10% Dis" (and her entire debut album) wasn't so effin' good.

One of the best to pick up a mic, KRS-One has a very solid discography, including the club banger "Step Into a World."

Preemo doing his thing.

EDITING NEEDED
Another instance in which several songs could have been lifted from the album and included here, as that "36 Chambers" album is the result of an immaculate conception.

Who's playing that noodling piano? Liberace was never this cool.

"Life as a shorty shouldn't be so rough." Despite what the chorus might suggest, Wu-Tang are not spitting about being rich, but rather how the pursuit of money by living foul leads to no good. The song highlights what happens to most YBM who do whatever it takes to get rich, and usually end up in jail on long, pumped up bids for their troubles. S

The one time I'm happy that CREAM means something monetary and not sexual, though I must point out that Method Man has morphed deliciously into a Staten Island DILF, even making the cover of Men's Health with a set of some seriously "swole" biceps and meaty man breastisis.

We often forget about "Whodini", a group that, before Run-DMC took the wheel, with the release of 1984's "Escape", were the first hip-hop album to chart within the U.S. top 40, and was also one of the first to be certified platinum by the RIAA. It was with 1986's "Back in Black" when I really started to take notice. "One Love" was the most melodic rap track ever and one of the year's best all around.

With his chest perpetually out, he never saw a button he liked. The Zorro hat and short leather Daisy Duke shorts were, let's say, a look, for sure.


Saw them in concert and even though they were billed as openers, I remember that they stole the show from LL and Run-DMC.

In a YouTube video, Jay-Z talks about how he warned all other MCs to put their records out NOW because he knew from solid sources that this New Jack named 50 Cent was about to mop up the entire industry when his single drops. Jay may have messed up with Becky with the Good Hair, but he made absolutely no mistake about this prediction.

With a mammoth beat, "In Da Club" is a remarkably good single, perhaps the best of the early 2000s. The Game is a more skilled and thoughtful rapper and Jay-Z himself was light years ahead in creativity, but when it comes a song that just rules like Idi-fuckin'-Amin, "In Da Club" is in a league all its own.

Daddy-O from Stetsasonic provided the production and one of the most recognizable and sampled beats in rhythmic music.

MC Lyte threw in her two cents with "10% Dis", the slight bowlegged little sister to "Top Billin´"

One of the best to ever do it, period. And one of the reasons 1988 was such a stellar year for rap. Credit also to Marley Marl.

The extremely attractive Kane allowed himself to be talked into becoming rap's Luv Man, a career move thought up by somebody on co-Kane as it prematurely derailed what should have been a music career that rivaled those of LL or Ice Cube.

Rock the full album version with the extra verse.

I'm always left shook by how young these guys were when they dropped "The Infamous".
Mariah sampled it for one of her best songs ever, "The Roof (Back in Time)"

I recognize those places they're driving by and nowadays, those areas of Queens are bubbling over with some of the cutest cafes and Bubble Tea shops you've ever seen!

Black. Bougie. British. Raised in Baychester, the Bronx.

Rick was no slouch as he attended the highly competitive specialized LaGuardia High School of Music & Arts alongside Dana Dane.

On paper, none of this should have worked in the hyper-masculine streets of New York City, but it did. Boy, did it. When it comes to royalty, Slick Rick is our Princess Diana of Wales, a character and personality of near-mythic standing. And "Children's Story" has plenty to do with his high ranking in the world of hip hop.

When "Boyz-n-the-Hood" and "8 Ball" hit back in 1987, I had never heard of Compton and, unlike New York City, I had absolutely no desire to go there. When the "Straight Outta Compton" cassette dropped a little more than a year later, I became completely convinced: "I sho'nuff ain't evah going to Compton", a promise to myself I have kept to this very day."

N.W.A. made Southern California seem like the worst place on earth, but the music on their sophomore album was undeniable. It exploded out of the speaker like Molotov cocktail and lit everything around it on fire.

But it was also danceable, highlighting how Dr. Dre always kept one foot in the mainstream. This album made me so angry about the fact that my Suzuki Samurai had a nice-sounding, but not powerful stereo system. It had been just fine for bopping down the ave singing Anita's "Same Ole Love", but bombastic jams like "Straight Outta Compton" required a stereo system with a powerful amp and sub-woofers, not the Milton Bradley one I had bought at K-Mart.

Proof that these were truly geto boys can be seen in their inability to spell ghetto. We can place the blame on No Child Left Behind.

But a higher level of public education would not have done anything to improve on "Mind Playing Tricks on Me", one of the most disturbing and cinematic songs ever released.

I was already disturbed by the album cover with Bushwick Bill either entering or leaving hospital without an eyeball. (Probably leaving if the picture was taken in one of America's free clinics.)

Isaac Hayes sample

Not one of the three Preemo songs were released as singles.

Any of the songs could have made the list, but those three for me are the cream of the crop

My attempts to ignore/avoid/under-appreciate West Coast rap officially came to an close with the release of "Nuthin' but a 'G' Thang", the absolute epitome of party rap. Everything about this record is perfect from the beat, the groove, the sample, the embellishments, all headed up by the worm-like and extremely charismatic Snoop Doggy Dogg.

Boy. Did we misjudge Ice Cube or what?

On his diss track "'Til the Break of Dawn", LL claims that he took Ice-T's albums straight to the bathroom to buss a nut to titty-ful model, T's wife Coco. Careful, L. Betcha that I wasn't the only teenage boy who took YOUR album to the same place for the same purpose. LL was my first, full on boy crush, clearly the most beautiful face, flattest abs and most solid biceps in the business. And all that lip-licking just made the package that much more enticing.

But you know what? L.L. Cool J was also quite a wordsmith and talented rapper, not just a pretty face. And boy was that face a pretty one. (I hope the dipship in the Def Jam marketing department who chose to put a picture of a boombox on the cover of his album instead of a pic of Cool J shirtless, sagging and reaching for something on a high shelf got 86'd for his mistake. The album would have gone triple platinum on the cover art alone.)

As a product the direction R&B was taking back in '82, it was not a stretch to think that rap would also be taken in a more cosmic direction. Harold Faltermeyer, Jonzun Crew and George Clinton were all on the ship and it didn't take long for rap to follow suit.

In my opinion, this cosmic rap wasn't sustainable because as rap began focusing more on the artist, less time was spent on production, especially with the availability of James Brown records without having to pay anything.

This might well be the very first rap song I learned all the words to from start to finish.

With one wave a a magic wand, disco rap went up in a puff of smoke. Up until this point, Kurtis Blow was arguably the biggest name in rap with a lot of radio-friendly and melodic songs that carefully mixed R&B and rap. Run-D.M.C, under the brilliant guidance of Larry Smith, who had also been instrumental in Blow's early success as a writer and session musician, stripped back all of the live instruments and laid their sound on top of mechanical beats produced by a drum machine and little else. This groundbreaking approach would rip rap music up from its roots and create the template for the genre until sampling took over.

I was not into Black guys back then, but before LL, I think D.M.C. was my first black-boy crush. Not only did I think he was sexy as phuck, I couldn't stop looking at the roundness of his profile booty on the back cover of this album. I know it's like saying you have a crush on your uncle Swee' Pea, but my hormones were raging and I wasn't quite sure where to direct all that energy. D.M.C.'s butt was a good place as any.

I was still a pre-teen when "The Message" hit the scene, so it's understandable that I could not identity with most of the lyrics in the song. I really couldn't put the broken glass, the roaches, the rats and the pissings into any real context. (A neighborhood boy had a friendly white rat with beady red eyes as a pet and that may have been the only rat I'd laid eyes on up until that point. Something told me that Melle Mel wasn't referring to the Noodles the Rat-type of rat in "The Message").

That lack of reference did nothing to stop me from becoming mesmerized by this track,

New York City must've looked like a scary place to housewives from Des Moines back then. I have to admit that I was a big fearful of the Rotten Apple. The South Bronx. Delancey Street. Shaolin Island. They all seemed so socially socially when my favorite rap artists talked about them. And then seeing the "Fight the Power" video where the streets of Brooklyn looked all militarized, like right on the edge of exploding into something that would require the police to use fire hoses to break up. I was scared, but I was also intrigued because those images matched the angst and aggression of "Fight the Power".

Did Chuck D. just call Elvis a racist while Flava Flav politely asked us to mother-fuck him and John Wayne? We had heard cursing on wax, but never had we experienced such a blatant attack on U.S. institutions. I was not aware of the racial beliefs of neither one of those guys, but I could not help that Public Enemy was on to something that I needed to pay attention to, despite my lack of Black self-awareness at the time.

Why couldn't I be a fly on the wall to see James Brown's reaction as he began to hear all these raps songs that stole from his catalog? I could have then followed him out to the mailbox as he waited in vain for the royalty checks to start rolling in.

I have to be honest and confess that I didn't know most of the backing tracks back then came from James Brown, so my appreciation for his contributions to music grew from listening to rap music, and not the other way around. And it was stellar tracks like "You Know You Got Soul" that really did it for me.

It was not easy to choose which groundbreaking single from "Paid in Full" to add here since the whole record plays like a greatest hits collection. This period of around 1986 through 1989 was especially important for us country folk because we were able to go to the wrecka stow and actually purchase singles and albums by rap artists. The days of stopping on the side of the highway and buying record out the trunk of a parked car of a Cholo wearing a Kangol were officially over.

This single changed the course of my life, as my love of hip hop had been waning. I didn't feel that West Coast vibe, there was nothing gritty or urgent about it. And as a newly arrived New Yorker, I didn't feel like "You Can't Play with My Yo-Yo" meshed with what I was seeing around me on the streets of Brooklyn.