Hip-hop And You Do Stop is a series chronicling A.V. Club writer 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.


Memory can be an imprecise instrument. We have a tendency to recall not how things happened so much as how it felt they happened. In my mind, I bought a cassette tape of DJ Jazzy Jeff & The Fresh Prince’s He’s The DJ, I’m The Rapper in 1988 when I was 11 and lived in the comfortably middle-class suburb of Shorewood, Wisconsin with my government bureaucrat father and graphic-designer stepmother. It’s just as possible I got the album a few years later when I was 12 or even 13 and living with my single-parent father on the North Side of Chicago as he struggled and failed to hold down a series of low-paying jobs. In a sense, it doesn’t matter when I actually bought He’s The DJ, I’m The Rapper. It sure felt like it belonged to my relatively secure, stable childhood and not to my terrifying and uncertain adolescence, which had a different, harsher soundtrack.

Listening to He’s The DJ, I’m The Rapper 24 years later, I’m struck most by its wholesome innocence. Where gangsta rap was designed to terrify, He’s The Rapper, I’m The DJ was designed to soothe. The album occupies a comfortingly middle-class world devoid of any complication that couldn’t get resolved in a typical sitcom episode. In that respect, turning Fresh Prince Will Smith into a sitcom star a few years later was redundant: He’s The DJ, I’m The Rapper is essentially an audio sitcom, a brightly colored musical romp through the mild wackiness and minor complications of being a teenaged rap superstar. The future two-time Oscar-nominee’s breakout album is so accessible and kid-friendly that it might as well have been called My First Hip-Hop Album. One of my favorite headlines from The Onion reads, “Will Smith: The Black Man Everyone At Work Can Agree On,” and that was true from the beginning. Intentionally or otherwise, He’s The DJ, I’m The Rapper reassured white parents that hip-hop was nothing they had to worry about, that it was simply a new form of family-friendly entertainment instead of an incendiary cultural movement or force for social change.


On He’s The DJ, I’m The Rapper, Smith seems to be smiling with each cheerfully delivered punchline and inoffensive wisecrack. He sounds as eager to please as a golden retriever puppy and roughly as difficult to resist, a cheeky wisenheimer who raps about videogames, horror movies, chasing girls, shopping with his mom, and other PG-rated subjects. He even raps about sex in a strangely asexual fashion: Forget referring to women as bitches and/or hoes; on both “Parents Just Don’t Understand” and “Let’s Get Busy, Baby,” Smith refers to the object of his desire as “toots,” as if he were a fast-talking flimflam man in a Damon Runyon story and not a teenager looking to get laid. The closest he comes to sounding risqué is when he raps, “Listen up toots / I like your looks / I used to see girls like you in them girly books.”

Smith doesn’t just sell each line with vaudevillian shamelessness; he practically nudges listeners in the ribs with every cheesy punchline and quip. Instead of taking listeners inside an often hermetic and insular subculture, DJ Jazzy Jeff & The Fresh Prince met middle-of-the-road, mainstream America on its own terms, beginning with the album’s opening track, “Nightmare On My Street.”

It’s telling that the only real horror on the album is of the supernatural variety, arriving when Smith goes to see Nightmare On Elm Street along with DJ Jazzy Jeff (who occupies a sidekick role here not unlike the one he’d go on to play on The Fresh Prince Of Bel-Air), beatboxer Ready Rock C, and their respective dates. “Nightmare On My Street” posits The Fresh Prince as an Archie-like quintessential American teenager who encounters supreme evil in the form of a disfigured mass murderer and fights him with the primary weapons at his disposal: corny jokes about Freddy’s appearance and patronizing offers to maybe hang out with him sometime next week, when he’s feeling less tired. He’s The DJ, I’m The Rapper is a product of the Reagan ’80s, but it feels very 1950s as well. “Nightmare On My Street” is hip-hop’s agreeably cornball answer to “Monster Mash.”


Even as a teenager, Smith was a genius at branding. He’s The DJ, I’m The Rapper follows the big crossover move of “Nightmare On My Street” with a song that doubles as a veritable infomercial for the album that preceded it. On “Here We Go Again,” over an airy, jazzy groove—Smith’s DJ certainly earned his nickname—The Fresh Prince blames the entirely reasonable yearlong gap between 1987’s Rock The House and 1988’s He’s The DJ, I’m The Rapper on the earlier album’s incredible popularity. The implication seems to be that DJ Jazzy Jeff & The Fresh Prince would happily deliver two or three albums a year if only they didn’t have to tour the world so relentlessly for the benefit of their adoring universal audience.

Smith is so self-assured and polished in his presentation on He’s The DJ, I’m The Rapper that it’s jarring to hear him rap “All the homeboys that got AIDS be quiet” and “All the girls out there that don’t like guys, be quiet,” on “Live At Union Square (November 1986).” Such statements sound like the product of the time when Eddie Murphy delighted a nation with his homophobic hilarity while wearing a skin-tight red leather suit. Apart from those misguided statements, though, the track doubles as a fun-sized primer on the development of hip-hop, with the duo paying reverent homage to old-school legends like Grandmaster Caz, Melle Mel, and Mr. Magic while DJ Jazzy Jeff spins the classic breaks. Smith trots out just about every hoary crowd-participation bit (yes, even getting the fellas to say “hoooo” and the ladies to say “ow”) for the benefit of an audience that, like myself and other neophytes my age at the time, had probably never heard them before and certainly wouldn’t be able to identify them as clichés.

Like “Girls Ain’t Nothing But Trouble,” the breakout single off Rock The House, “Parents Just Don’t Understand” expresses a sentiment designed to appeal to every teen and pre-teen in the universe. The stakes start out refreshingly, even bewilderingly low: In the first vignette, Smith finds his reputation among classmates endangered after his mom buys him embarrassing clothes. Shit gets real in the second vignette, however, when Smith “borrows” his parents’ Porsche—it’s hard to feel too sorry for a teenager with access a Porsche, no matter the circumstances—after they go on vacation and ends up getting busted by the cops after picking up a hot girl who turns out to be a “12-year-old runaway.” Things look bleak after Smith is arrested, but the real consequences emerge when the rapper frets, “There was no way for me to avoid being grounded.” There’s something soothingly quaint about the idea that a black kid could get arrested with an underage girl and all he’d have to worry about is being grounded for a few weeks.

He’s The DJ, I’m The Rapper is awfully diligent in teaching neophytes about the basics of hip-hop culture, beginning with its title. The second half of the first double album in hip-hop history is largely dedicated to DJ tracks like “DJ On The Wheels,” “Hip-Hop Dancer’s Theme,” and “Jazzy’s In The House” in addition to the aforementioned beatboxing tracks. A star from day one, Smith could afford to be gracious and generous to his supporting cast. He’s The DJ, I’m The Rapper consequently offers something for everyone: The first half is designed to conquer radio and MTV while the second half is custom-made for the house parties that were hip-hop’s early home and proving ground. In part because The Fresh Prince’s partnership with Jazzy Jeff was a true partnership of equals, at least initially, He’s The DJ, I’m The Rapper Trojan-horses a lot of genuine hip-hop into an album with clear crossover aspirations.


Smith’s been silent musically since 2005, but before that, an air of pointlessness settled over every album he’s put out since He’s The DJ, I’m The Rapper. Smith accomplished everything he needed to get done musically while he was still a teenager. Smith completed the work Run-DMC began in making hip-hop palatable for the widest possible audience. Some musicians are fated to be great artists. It was Smith’s destiny to be a crackerjack entertainer, to knock down doors with boyish charm and cheeky good humor, to be the Sidney Poitier or Bill Cosby of hip-hop, a freshly scrubbed icon of assimilation so obviously gifted no one in their right mind could deny his talent and charm.

Where Smith was almost Eddie Haskell-level ingratiating, N.W.A. was nakedly confrontational. Where Smith was inclusive, N.W.A. dared audiences to hate it. That was part of gangsta rap’s power from its inception: It thrived on hate more than love. Today, it’s difficult to imagine just how bracing, revolutionary, and shocking Straight Outta Compton felt at the time. In some ways, Straight Outta Compton became a victim of its own massive success and influence, as its innovations long ago devolved into tiresome clichés. Straight Outta Compton didn’t just lay the groundwork for gangsta rap; it introduced themes, tropes, and attitudes that would soon become the subgenre’s conventional wisdom.


There’s a wonderful line from the musician-narrator of Stew’s musical Passing Strange about the sublime absurdity of spending your adulthood living out the consequences of decisions you made as a stoned teenager. In the same respect, it’s absurd—and not in a sublime way at all—that gangsta rap still largely hews reverently to the poisonous gender politics expressed by primary N.W.A. lyricists MC Ren and Ice Cube while they were still angry teenagers.

There are few things in the world more terrifying to teenaged boys than the power of teenaged girls. On the Straight Outta Compton Ice Cube spotlight track “I Ain’t Tha 1,” the rapper attempts to negate that terrifying power by fundamentally denying the humanity and agency of women, reducing the complicated, messy, and crazy-making dance of sex and romance to a simple formula: Men want sex, women want money. And it’s every real man’s solemn duty to get the sex he craves without sacrificing any of his hard-earned scratch.


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This isn’t just patently unfair to women, but men as well. But it factors into the album’s obsession with instant gratification. On Straight Outta Compton, the members of N.W.A. want everything and they want it right now. Because the album is a work of adolescent wish-fulfillment, N.W.A. gets exactly what it wants when it wants it, which is right fucking now. Where Smith uses charm and guile to campaign for what he wants, N.W.A. simply takes what it desires, at gunpoint ideally.


Straight Outta Compton consequently benefits from a ferocious sense of urgency. It’s an album that takes place entirely in the present tense, with no thought or consideration given to a future that might not ever arrive. As the album’s producer, Dr. Dre’s genius lies in finding a sonic vocabulary to express the pummeling intensity and you-are-there immediacy of the lyrics, a dense sonic collage of blaring horns, screeching tires, furious scratching, and deftly executed sound bites from a dazzling array of sources.

Straight Outta Compton is a brilliant exercise in self-mythologizing. N.W.A.’s lineup included two moonlighting college kids (Brown dropout MC Ren and Phoenix Institute Of Technology architecture student Ice Cube, the group’s primary lyricists), two refugees from a fancy-dressing, flamboyant electro group named World Class Wreckin’ Crew (Dr. Dre and DJ Yella, who handled production and scratching respectively), and a tiny Jheri curl enthusiast and small-businessman with a high-pitched voice (Eazy-E). And on the album-opening title track they came off as the toughest motherfuckers on the planet.


The album opens with Dre uttering iconic words that heralded a revolution in hip-hop—“You are now about to witness the strength of street knowledge”—before Ice Cube’s gruff baritone detonates alongside a furious horn blast that seems to signal the opening of an urban apocalypse. Cube wastes no time mythologizing himself as a “crazy motherfucker named Ice Cube” from a “gang called Niggaz Wit’ Attitude” in a sociopathological rant in which he boasts of possessing a “crime record like Charles Manson.” The lines are delivered with effortless authenticity, but are so preposterously over-the-top that they come off as a cartoon of masculinity.

This is especially true of Ren’s next verse, in which the gruff MC promises to “shoot a motherfucker in a minute / I find a good piece of pussy, and go up in it” before promising listeners, “So if you’re at a show in the front row / I’ma call you a bitch and a dirty-ass ho.” Ren doesn’t just have contempt for enemies and rivals; he hates his fans and the women he sleeps with as well.


There’s something at once comic and strangely pure about the rage on display on Straight Outta Compton. On “Fuck Tha Police,” the group’s rage is directed toward racist cops and corrupt authority figures, but for much of the album, the rappers brazenly assault anyone and everyone pretty much for the hell of it. They’re living out the sociopathic fantasies of angry teenagers everywhere in a realm where they possess all the power.

Just as Smith worked hard to establish the tightness and importance of his supporting crew, the members of N.W.A. spend Straight Outta Compton acting as if they’re such a tight-knit bunch of BFFs that they live in the same house, borrow each other’s clothing (not difficult, since they shared a denim-and-Raiders-hat-heavy aesthetic), and march merrily down the street in unison like The Monkees. On Straight Outta Compton, MC Ren, Ice Cube, Dr. Dre, and Eazy-E are constantly setting up each other’s verses, rapping about each other, and generally serving as each other’s hype men in a one-for-all, all-for-one spirit that would soon become ironic in the wake of the group’s bitter break-up. Maybe Ren, Dre, and Eazy-E wouldn’t have had to spend so much time knocking Ice Cube down after he split from the group to go solo if they hadn’t devoted so much of Straight Outta Compton to building him up. (Then again, along with Ren, Cube basically wrote all of the album’s lyrics, so sometimes he was simply putting pro-Ice Cube sentiments in his groupmates’ mouths.)


Of course, it works the other way as well, especially on “Gangsta, Gangsta” the final third in the album’s opening holy trinity, which established the sound, attitude, and intensity of gangsta rap. On the album’s third track, the beat switches to the undulating funk of Ohio Players’ “Funky Worm” (a classic breakbeat that, coincidentally, would also be used on the later DJ Jazzy Jeff & The Fresh Prince track “Boom! Shake The Room”) and Ice Cube sells his bandmate as “a li’l gangsta short in size / A T-shirt and Levis is his only disguise / Built like a tank yet hard to hit / Ice Cube and Eazy-E cold runnin’ shit.”

Eazy-E didn’t look or sound tough or intimidating. He looked and sounded silly and cartoonish, but he had men who did look and sound tough and intimidating on his payroll to broadcast his unimpeachable street credibility. (It was Eazy, along with much-vilified manager Jerry Heller, who ran the group’s label, Ruthless Records.)


Straight Outta Compton is a strange Frankenstein’s monster of an album. It combines the aforementioned opening salvo of gangsta rap touchstones with a trio of remixes (“Compton’s N The House,” “Dopeman,” and “8 Ball”), an uncharacteristically mainstream crossover attempt highlighting Dr. Dre as a rapper (“Express Yourself,” on which the future creator of The Chronic raps, “I don’t smoke weed or sess cause it’s known to give a brother brain damage”), and an album-closing electro dance track, “Something 2 Dance 2,” that seems to belong in a different universe than the rest of the album.

Then again, it didn’t ultimately matter that Straight Outta Compton was a mixture of remixed old material and new provocations. The album could have been an EP containing just the first three tracks and it still would have had a seismic effect on the nascent genre of hip-hop. Straight Outta Compton didn’t invent gangsta rap. Schoolly D and Ice-T both released gangsta-rap songs before Straight Outta Compton hit, but the album perfected the burgeoning subgenre while introducing a formidable collection of solo artists who would play a central role in its development, most notably Ice Cube and Dr. Dre. N.W.A. first surfaced with the Dr. Dre-produced 1987 compilation album N.W.A. And The Posse and ended its run with 1991’s Niggaz4Life, but four years was all it took to change pop music and pop culture forever. You’d have to look to the equally short-lived careers of the Velvet Underground, Big Star, and the Sex Pistols to find seminal acts that changed music as profoundly and permanently as N.W.A. did in such a short a period of time.


It would be difficult to imagine two more radically different rap icons than Will Smith and Ice Cube, even though they both ended up halfway abandoning careers in music to pursue acting. Then again, maybe they aren’t so dissimilar: Both were unusually savvy, calculating, and business-minded even as teenagers in the blinding glare of the spotlight. Smith and Ice Cube didn’t just survive the kind of massive fame and fortune that destroys weaker souls; they thrived on it. To paraphrase Jay-Z’s famous line, they weren’t businessmen, they were businesses, man. When the record industry began to die, they shifted their business models to deemphasize hip-hop and focus on family entertainment and, in Smith’s case, breeding the next generation of genetically perfect instant-superstars.

Even as an unusually astute young man, Ice Cube had his mind on the bigger picture. When Jerry Heller and Eazy-E tried to re-sign Ice Cube after the massive, worldwide success of Straight Outta Compton with what he considered inadequate compensation for his contributions to the album, Ice Cube told them to go fuck themselves and went solo with spectacular results, beginning with his essential, Bomb Squad-produced 1990 solo debut AmeriKKKa’s Most Wanted. Nearly a quarter-century after Straight Outta Compton, Ice Cube’s career has come full circle. The incendiary provocateur who eviscerated Hollywood’s deplorable racial politics long ago on Public Enemy’s “Burn Hollywood Burn” is now one of the producers behind an eagerly anticipated N.W.A. biopic called, naturally enough, Straight Outta Compton. As a veteran television and film producer, Ice Cube now looks primed to finish the job of self-mythologizing he began as a teenager with a little bit of gold and a pager.


In 1988, DJ Jazzy Jeff & The Fresh Prince and N.W.A. defined hip-hop’s polar extremes. They wore white and black hats as rap’s clean-cut heroes and villains. But as the years went on and hip-hop grew more alienating, graphic, and extreme, the genre and its fans had progressively less use for good guys like Smith. He was a terrific gateway to the genre, but as life got darker and more complicated, I graduated to harder stuff. When He’s The DJ, I’m The Rapper came out, Smith was the norm, a smiling, family-friendly rapper in the tradition of Kurtis Blow, The Fat Boys, Whodini, Run-DMC, and The Sugar Hill Gang By the time Smith released Lost & Found in 2005, his wholesome ways and aversion to profanity made him a weird anomaly in hip-hop, a strange throwback to a pre-Straight Outta Compton era.

But if conventional heroism is increasingly out of favor in hip-hop, it remains in vogue in television and movies. The man behind “Fuck Tha Police” recently played a scowling cop in the hit adaptation of 21 Jump Street, but as he’s mellowed with age, Cube’s recording career has grown increasingly irrelevant, like a vestigial tail. Cube no longer seems to rap because he has anything interesting or provocative to say: When I saw him perform last summer at the Insane Clown Posse festival Gathering Of The Juggalos, his primary focus was reminding the audience every few minutes that he was from the West Coast, repped the West Coast, and generally thought the West Coast was great—because that was something he used to do and remained a part of his business model, for the time being at least.


Ice Cube reportedly has a new album coming out soon, but hip-hop seemingly hasn’t been his main focus in years, if not decades. Like Smith, Cube is an entertainer above all, a potent and enduring brand that transcended his hip-hop roots long ago. As the years go on, the differences between these two seemingly disparate survivors grow more inconsequential, while their similarities grow increasingly pronounced.

Up next: De La Soul’s 3 Feet High And Rising and Beastie Boys’ Paul’s Boutique elevate the hip-hop-centric art of sampling.