Hip-Hop And You Do Stop is a series chronicling Nathan Rabin’s deep love for (and growing estrangement from) hip-hop through the filter of golden-age and ’90s hip-hop. Each entry documents a year in the genre’s development, beginning with 1988 and concluding with 2000.


In previous installments of this series, I’ve written about how The Artist Formerly Known As The Fresh Prince, MC Hammer, and Vanilla Ice experienced spectacular, unprecedented commercial success with personas that all but disappeared from hip-hop and pop culture over the ensuing years. Will Smith continued to have success throughout the ’90s and even for a period in what is universally known as the Willennium, but his massive success did not create a market for goofball, wholesome, borderline-novelty rappers peddling proudly silly raps about horror movies, getting grounded, and videogames.

MC Hammer followed up his 1990 breakthrough Please Hammer Don’t Hurt ’Em with the massively successful 1991 follow-up Too Legit To Quit, which sold 5 million copies en route to teaching the world all manner of nifty hand gestures, but by 1994’s The Funky Headhunter, Hammer had dropped MC from his name, dramatically changed his image, and sported one of MTV’s most visible erections in the infamous music video for “Pumps And A Bump” in a desperate, doomed attempt to keep up with the times. Vanilla Ice was nowhere near as lucky. There would be no Too Legit To Quit-style follow-up smash for Vanilla Ice, just a seemingly endless personal and professional freefall.


What happened to the clean-cut rapper with his friendly grin, acrobatic dance moves, and wholesome air? For an answer, let’s examine the post-Too Legit To Quit career of MC Hammer: In spite of that album’s success, Hammer, one of the bestselling rappers of all time, consciously or unconsciously reinvented himself in the image of friend, fellow Oakland rapper, and professional and personal opposite Tupac Shakur. On the cover of The Funky Headhunter, a scowling Hammer sports a black sleeveless undershirt and jeans against a bare backdrop. Hammer collaborated with Tha Dogg Pound and, like 2Pac, signed to Suge Knight’s Death Row Records—a label famously funded with the proceeds from Vanilla Ice’s To The Extreme after Knight allegedly dangled Ice out a window to “convince” him to give publishing credits for “Ice Ice Baby” to an artist Knight represented called Earthquake. Hammer was fortunate enough to never release an album during his tenure on the label.

2Pac was such a seismic cultural force that the history of hip-hop can roughly be divided into two eras: pre- and post-2Pac. 2Pac didn’t invent gangsta rap: As he acknowledges on his 1991 solo debut, 2Pacalypse Now, he was consciously following in the footsteps of Ice Cube as well as more traditionally political rappers like KRS-One and Public Enemy. But he defined, refined, and perfected the image, style, persona, and especially the attitude of gangsta rap, the middle-finger bravado and sneering swagger that said, “Fuck the world” before his rhymes (and song titles) indelibly conveyed the same message. 2Pac didn’t just present an appealing new hip-hop archetype. He was so wildly influential and enduring that he damn near created the hip-hop archetype. Chances are, if you close your eyes and imagine a rapper, he probably looks an awful lot like All Eyez On Me-era 2Pac: shirt off to reveal a rippling six-pack, pants sagging low, scowling at the camera with a look of dour intensity. Will Smith, MC Hammer, and Vanilla Ice failed to spawn imitators in spite of their incredible success, but even today, over a decade and a half following his death, hip-hop and particularly gangsta rap is littered with what can charitably be called 2Pac’s creative progeny and less charitably called knock-offs. Before the likes of Master P, Ja Rule, 50 Cent, and countless others could experience incredible success with variations on 2Pac’s tormented, sensitive-thug persona, 2Pac created that persona out of selective elements of autobiography, generous dollops of self-mythologizing, and bits borrowed from artists he admired.


Throughout his life, Tupac Shakur was a work in progress: He was constantly evolving and changing. 2Pac might have ended his life as the quintessential West Coast gangsta rapper and thug-life advocate, but he didn’t move to California until he was 17 years old. Before relocating, Tupac was a poetry-loving theater kid, first in Harlem, then in Baltimore. And before he became the voice and face of black rage, 2Pac was a roadie and back-up dancer for Digital Underground—the light-hearted George Clinton disciples who gave the world “The Humpty Dance” and “Doowutchyalike”—and a bit player in the poorly received Dan Aykroyd comedy Nothing But Trouble.

Shakur changed dramatically over the course of his eventful 25 years on the planet, but the elements that defined his persona were pretty much in place when he released 2Pacalypse Now in 1991. 2Pacalypse Now posits its creator as, to paraphrase Malcolm X’s resonant turn of phrase, the hate that hate made, a defiant black intellectual as well as the literal and figurative progeny of the Black Panther movement, a man growing up in a viciously racist society where every black male is judged as guilty until proven innocent by a power structure intent on suppression.


“Trapped,” the album’s second song and third single, doubles as a statement of purpose that portrays the world as a prison all the more poisonous and destructive for giving its inhabitants the illusion of free will. The song warns of a world where threats are everywhere and staying in the street life for too long inevitably results in violent death or long prison terms that, as 2Pac notes dourly, leave ex-cons worse off than when they went in. Though within the grim, 2pacalyptic world of 2Pacalypse Now, there’s no real difference between physical prisons and the metaphorical prison of the ghetto.

2Pac reunites with Digital Underground’s Shock G on the song and its accompanying video, but the context is radically different from their work in Digital Underground or subsequent hit collaboration “I Get Around.” G was famous for wearing a ridiculous Groucho nose in his Humpty Hump guise and rapping about once getting busy in a Burger King bathroom, but on “Trapped” he cuts a much more radical, revolutionary figure as he responds to 2Pac’s verses with a whispered, “They can’t keep the black man down.”


On “Words Of Wisdom,” 2Pac adopts a coffee-shop poetry-slam delivery and channels his inner Gary Busey to posit one of the most notorious and hurtful words in our language as an acronym for “Never Ignorant, Getting Goals Accomplished.” Like NWA on “Fuck Tha Police,” on “Words Of Wisdom” 2Pac stands in judgment of a society and a justice system that casts judgment on him. As the song draws to a close, 2Pac passionately argues, “I am what you made me / The hate and evil you gave me” before explicitly connecting the dots between the personal and the political, the Black Panthers that spawned him and the black nationalist rappers who inspired him. He presents himself, then Ice Cube and Da Lench Mob, Above The Law, Paris, and Public Enemy as America’s nightmares before ending his honor roll with Mutulu Shakur, Geronimo Pratt, and Assata Shakur, black nationalists who also happened to be his stepfather, godfather and step-aunt, respectively. For 2Pac, the government’s persecution of black radicals wasn’t some abstract social problem; it was something that directly and negatively affected the lives of many of the people closest to him.

2Pac was a man of furious contradictions, equally devoted to denigrating scandalous groupies in his voluminous body of sex songs and uplifting women in timeless message songs like “Keep Ya Head Up” and “Brenda’s Got A Baby,” which was the first single from 2Pacalypse Now and one of the rapper’s first signature hits. It’s a testament to how ballsy and uncompromising 2Pac was at the beginning of his career that his first solo single is an unrelentingly grim character study of a barely literate 12-year-old who grew up with no mother and a junkie dad who gets impregnated by her cousin, then throws the baby in the trash. That’s when things get really depressing: The pre-teen mother of the title is reduced to selling crack and then prostitution before ending up dead, just another casualty of a crooked and corrupt system. There’s nothing in “Brenda’s Got A Baby” to undercut the almost unbearable grimness: It begins sad, then grows sadder en route to an ending that’s at once tragic and preordained. 2Pac catalogs the gauntlet of urban horrors the protagonist endures with a deep baritone that radiates empathy and compassion. This is a song that feels more like journalism than pop music, more a harrowing docudrama than an exercise in escapism. (The song was inspired by an article Shakur read about a pre-teen mother who abandoned her baby.)

2Pacalypse Now is an unrelentingly dark, appropriately apocalyptic manifesto that purposefully eschews the goofy mood-lighteners like “I Get Around,” “California Love,” or “All About U” found on subsequent albums. There’s a purity to 2Pac’s rage that became diluted with gangsta posturing and rampant thematic recycling during his Death Row days. 2Pac raps with a density and urgency here that suggests he feared that this might be his first, last, and only opportunity to share his pain with an alternately indifferent and cruel world. Even at the beginning of his recording career, 2Pac had his end in sight. Part of this was fatalism, part of this was self-mythology, but as history illustrated, it was also rooted in reality. It’s not paranoia if they genuinely are after you.


2Pac’s persona was already firmly established when he made 2Pacalypse Now, but the man, the myth, and the legend the world came to know and revere as MF Doom (and also as Doom, Metal Fingers, King Geedorah, JJ Doom, Dangerdoom, Madvillain, and Viktor Vaughn, among other aliases and side projects) emerged in 1991 in a form radically different from his current persona. The dramatically different guise he adopted later in his career was entirely deliberate: It would be difficult to imagine a more extreme way of distancing yourself from an old identity than by changing your name and performing only while wearing a mask that completely obscures your face. But that wasn’t enough for MF Doom. He doesn’t just wear the mask while performing; he refuses to be photographed without it. And he didn’t just change his name or developed a new persona; he changed his name repeatedly and developed so many personas that it can be hard to keep track of them all.

That’s just not dramatic. That’s pathological, even diabolical, but like superheroes and supervillains alike, the man born Daniel Dumile had a damn good reason to want to distance himself from an early life filled with pain, disappointment, and almost inconceivable tragedy. In the same traumatic week in 1993, Dumile’s group KMD was dropped by Elektra and his brother, groupmate, and producer Subroc died after getting hit by a car. If that wasn’t enough to make a man want to hide from the world and wear a mask all day, KMD’s second album, Black Bastards, was shelved due to controversy over cover art of a Sambo caricature being lynched.


But Doom was not always a wise, enigmatic man haunted by tragedy. As KMD’s 1991 debut, Mr. Hood, indelibly documents, he was once a boyish, carefree kid whose mind and sensibility had been liberated by the casual revolution that was 3 Feet High And Rising. Like Ol’ Dirty Bastard, there is no father to Doom style, but on Mr. Hood, Zev Love X (as Doom then called himself) owes a massive debt to the goofy humor, crate-digging weirdness, and relaxed, conversational delivery of De La Soul and in-house producer Prince Paul. A giddy Zev Love X acknowledged that debt on 3rd Bass’ “The Gas Face” (which Prince Paul also produced), the single that introduced him to the world, when he hailed Plugs 1, 2, and 3 as heroes patently undeserving of the scathing condemnation that is the Gas Face. (South African leader P.W Botha? That motherfucker, on the other hand, definitely gets the Gas Face.)

The almost childlike innocence that permeates Mr. Hood, in spite of its pervasive undercurrent of black nationalist rage, is reflected in the songs, or rather the sounds that KMD samples throughout the album. Mr. Hood samples Sesame Street extensively and takes its name and weird, loose structure from creaky old language-translation tapes that collectively create the character of Mr. Hood, a 1950s-style representation of stuffy white propriety who serves as an oblivious straight man to Zev Love X’s righteous exemplar of Afrocentric wisdom.


Mr. Hood tackles some of the same thematic ground as 2Pacalypse Now, but it does so with a playfulness and humor missing from 2Pac’s angry jeremiad. The single “Who Me? (With An Answer From Dr. Bert)” takes on institutionalized racism, racist caricatures, and Anglocentric conceptions of beauty, but it does so with a light touch and ingratiating goofiness. On Mr. Hood, Zev Love X is the friendly, grinning face of Black Power; the militant X in his name tellingly follows Love. On “Figure Of Speech,” X raps, “the motto goes: sex, drugs, and rock ’n’ roll / I prefer love, hugs, and hip-hop soul.”

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It’s strange today to imagine Doom agitating for love and hugs, but Mr. Hood engagingly cross-pollinates the righteous Five Percenter ideology of Brand Nubian (who guest on “Nitty Gritty,” a song that pointedly samples fellow travelers A Tribe Called Quest) with the D.A.I.S.Y. Age utopianism of De La Soul.


If Doom is an old soul, then Zev Love X was a divinely youthful spirit who rapped flirtatiously about peach fuzz and sampled Bert and Ernie. That innocence could not and would not last. Hell, it wouldn’t even make it past a single album. Like De La Soul, KMD’s follow-up was a marked departure from the good vibes and childlike tomfoolery of its debut. De La Soul named its follow-up De La Soul Is Dead; KMD went even further and named its long-shelved second album Black Bastards. The record industry and life ended up taking a toll on Zev Love X, but Mr. Hood indelibly remains a beautiful moment in his life and career, when he radiated youth, innocence, and boundless optimism.

Like KMD, Nice & Smooth were weird cousins of Native Tongues, specifically De La Soul. On 2001’s “Simply,” Trugoy even borrows the duo’s signature flow to profess, “Favorite MCs: Greg Nice and Smooth B,” while on Madvillain’s 2004 track “All Caps,” Doom impishly references the duo’s hit “Sometimes I Rhyme Slow” when he raps, “Sometimes he rhyme quick, sometimes he rhyme slow / And vice versa / Whip up a slice of nice verse pie / Hit it on the first try / Villain, the worst guy.”


But where KMD combined righteous black nationalist ideology with free-flowing goofiness, Nice & Smooth offered pure fun. Even the duo’s message songs, like the aforementioned “Sometimes I Rhyme Slow,” were unintentionally hilarious. “Sometimes I Rhyme Slow” is ostensibly a serious song about dealing with a partner’s cocaine addiction and the stress and pressure it puts on a relationship, but someone clearly forgot to tell Greg Nice, whose lead-off verse is his usual high-spirited gibberish. Where Smooth B’s verse tries and fails to add an element of substance and gravity to the duo’s high-spirited pop-rap with an uncharacteristically dark narrative about a girlfriend addicted to cocaine, Greg Nice kicks rhymes like “I’m sweeter and thicker than a Chico stick / Here’s an ice cream cone, honey take a lick / Or go to Bay Plaza and catch a flick” over a melancholy acoustic guitar lick purloined from Tracy Chapman’s “Fast Car.”

Nice & Smooth didn’t discriminate when it came to samples: Nothing was too cheesy or too comically white-bread. I fell in love with Nice & Smooth the first time I saw the music video for “Hip-Hop Junkies,” which transforms the intro to The Partridge Family’s “I Think I Love You” into the ultimate hip-hop guilty pleasure. While it’s difficult to imagine such an ostensibly non-hip-hop breakbeat working for anyone except Nice & Smooth, it’s the perfect fit for the duo’s unapologetic pop sensibility, massive hooks, and DayGlo cheerfulness.


“Hip-Hop Junkies” opens with The Partridge Family’s “Bah bah-bah bah bah-bah bah-bah bah” before Greg Nice unleashes, in rapid succession, a wonderfully stream-of-conscious combination of random pop-culture references (“Rickety Rocket was my favorite cartoon”), unrelated sentiments (“After marriage, the honeymoon”), and, for reasons known only to them, Valley Girl slang. (“I’ll be damned, gag me with a spoon.”) For Greg Nice, it didn’t really seem to matter if his lyrics made any sense. All that mattered was that they rhymed. Smooth B at least attempted to write verses that meant something, but Nice was content to string together bizarre non-sequiturs in a half-assed approximation of hip-hop verses.

Greg Nice couldn’t really sing, Smooth B couldn’t really rap, and neither could be deemed a deep or incisive or even particularly competent writer, yet that somehow didn’t keep them from releasing at least two terrific albums in 1991’s Ain’t A Damn Thing Changed and 1994’s lesser-known but massively underrated Jewel Of The Nile.


For Nice & Smooth it wasn’t about tongue-twisting wordplay, dense lyricism, or even basic competency: It was about creating a supremely entertaining gestalt at a time when hip-hop desperately needed Nice & Smooth’s mirth and merriment. Or maybe it was just that I needed Nice & Smooth’s mirth and merriment as a 15-year-old in a group home who lived for the moment he’d park himself in front of a television and watch Yo! MTV Raps, Rap City, or The Box upon coming home from school. To me, Nice & Smooth’s borderline nonsensical pop-rap provided a sense of escape when I needed it most.

I wasn’t the only one. Nice & Smooth hasn’t released an album since 1997, but their legend lives on via reverent tributes to the group from fans like De La Soul, The Roots, Doom, and DJ Premier, who famously sampled the duo on the seminal Gang Starr hit “Just To Get A Rep.” Ain’t A Damn Thing Changed rocked my world as an angry, impressionable 15-year-old. It was what I listened to when the cool kids all gravitated to Public Enemy. I related to that album’s humor, its goofiness, its loose-limbed infectiousness. And I responded to the same qualities in Del Tha Funkee Homosapien’s 1991 front-to-back masterpiece I Wish My Brother George Was Here, especially its glorious hit singles and videos “Dr. Bombay” and “Mistadobalina.”

Even in the fractured and wide-open hip-hop scene of 1991, Del was an odd character, a cousin of Ice Cube who shunned the gangsta posturing of his famous relative even as he rhymed over the same kind of George Clinton-derived P-Funk grooves that became synonymous with West Coast gangsta rap. (Eight of the tracks on I Wish My Brother George Was Here sample George Clinton and Parliament-Funkadelic.) But Del was equally apoplectic over outside threats to hip-hop’s soul, the everyday hassles of friends who sleep over and then refuse to leave, as well as the aggravations of riding the bus.


I Wish My Brother George Was Here is so much fun, with its mile-wide P-funk grooves and limber rhymes, that it’s easy to overlook its overwhelming obsession with authenticity in all its forms. Del was 18 when he recorded his debut, and like a lot of angry teenagers, Del defines himself as much by what he is not as by what he is. Since Del came of age professionally in 1991, he defines himself as the antithesis of MC Hammer and Vanilla Ice, pop-rappers he denigrates explicitly and implicitly on multiple tracks. Del’s contempt for these bozos borders on obsessive: He nearly talks about them more on his album than they talk about themselves on their own.

On I Wish My Brother George Was Here, Del fully embraces every teenager’s inalienable right to be pissed off by just about everything. He’s pissed off at pop-rappers who dance and wear shorts he considers excessively tight (the Vanilla Ice/MC Hammer diss track “Pissin’ On Your Steps” where he raps “Del is not a mean fellow / Just because I want to turn your dance shoes yellow”), scandalous women who view men as ATMs with penises (“Money For Sex”), light-skinned black women (“Dark Skin Girls”), male groupies (“Mistadobalina”), shiftless friends who crash on his couch without an exit strategy (“Sleepin’ On My Couch”), and inconsiderate fellow bus-riders (“The Wacky World Of Rapid Transit”).


In his own way, Del might have been just as angry as his cousin Ice Cube, who helped produce I Wish My Cousin George Here and has a hilarious, albeit almost subliminal presence on the album as his cousin’s comic foil. Here, Cube pops up to ask what in the hell a funky homosapien is (thereby acting as an audience surrogate), agitates for light-skinned black women when Del disparages them on “Dark Skin Girl,” plays the role of a shoe-snatching hood on “Hoodz Come In Dozens,” and finally describes Del as a weird “handkerchief-hat wearing motherfucker” who unwisely ignored his suggestion to pursue gangsta rap on the album-closing “Ya Lil’ Crumbsnatchers.” Underneath the good-natured ribbing, however, Cube clearly respects his cousin’s gifts and brazen eccentricity.

Plenty of rappers borrowed George Clinton’s sound, hooks, and grooves, but Del and Digital Underground were relatively unusual in also embracing the P-Funk pioneer’s absurdist, sometimes surreal sense of humor. Like KMD, Del figured out a way to make anger fun, to channel his rage into songs with the shiny, infectious surfaces of pop, but the underlying anger and social awareness of political hip-hop.


Anger was the underlying emotion behind a lot of hip-hop in 1991. 2Pac expressed it with ferocity and purity, while KMD and Del undercut that righteous rage with humor and playfulness. Nice & Smooth, meanwhile, just wanted to entertain the nice people. As men who sampled The Partridge Family and Tracy Chapman, they were in no place to attack the pop moves of their peers; instead they became the lovable, acceptable face of pop-rap, even if they never attained commercial success commensurate with their awesomeness or the respect and admiration their peers gave them.

Hip-hop, like all of pop culture, goes in cycles. In 1991, Del and KMD were responding to the zeitgeist-capturing runaway success of MC Hammer and Vanilla Ice. But in the years to come, hip-hop would be forced to respond to the cultural tidal wave that was 2Pac’s ascent and a 1992 album on a notorious, controversial label 2Pac would become synonymous with, for better but mostly for worse: Dr. Dre’s The Chronic, the album that made Death Row a major cultural force, not just a hip-hop heavyweight.


MC Hammer may have made, then lost, a fortune, donning the proverbial white hat and establishing himself as a clean-cut, milk-drinking role model, but hip-hop would soon find itself rooting for outlaws, antiheroes, and men who proudly proclaimed themselves to be America’s nightmare and had the criminal records to back up their claims. These men would move steadily from the sidelines to the mainstream, from a widely maligned subgenre to a massive commercial force that threatened to drown out and dominate all other rap subgenres. As we leave 1991 and approach the seminal year of 1992, we are officially leaving the heyday of the friendly rapper and entering the G-funk era, and the much different hip-hop world it created.

Up Next: Dr. Dre’s The Chronic and Pharcyde’s Bizarre Ride II The Pharcyde offer two different takes on California dreaming.