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Will Smith, a pioneering black nerd, helped raise and change rap music

Smith’s music career reveals an artist who believed in an Afrocentric American dream based on ambition, hustle and black pride

It was 2017, and Will Smith’s career seemed to have come full circle.

That’s when a sneak peek video surfaced featuring the world-famous entertainer performing a hip-hop version of the theme from Aladdin, a Disney musical, which opens in movie theaters Friday, featuring Smith in the role of the genie. For fans, the tune conjured memories of Smith’s career-launching hit “Girls Ain’t Nothing But Trouble,” which sampled the theme from I Dream of Jeannie, a 1960s sitcom about a genie.

The coincidence was eerily appropriate. With four Grammys, six American Music Awards, four NAACP Image Awards and two Oscar nominations, Smith’s career has seemed like a magic carpet ride, almost as if a wizard granted his wish of becoming one of history’s most successful entertainers. But while his big-screen achievements have been exhaustively examined, Smith’s musical accomplishments have received shorter critical shrift. From PTA-approved hits such as “Parents Just Don’t Understand” and “A Nightmare on My Street” to party-starting jams such as “Summertime” and “Gettin’ Jiggy Wit It,” Smith’s songs are so cursedly simple that some might argue they’re undeserving of serious critical scrutiny. We’re here to argue otherwise.

Smith’s career has seemed like a magic carpet ride, almost as if a wizard granted his wish of becoming one of history’s most successful entertainers.

Take, for example, the aforementioned Aladdin rap. Like most songs from Smith’s canon, the tune is a bouncy urban jam with lyrics of nursery rhyme simplicity.

“One fine day the bazaar was at peace, when the guards started running through the Agrabah streets

They were lookin’ for a lad and a beast, ’cause they was nabbin’ some yeast

The thickest of thieves in the Wild, Wild East …”

Notice how Smith sets up a story, stoking your desire to learn more. From his very first 1980s hits, he has repeatedly woven fablelike narratives into his songs, a creative device that makes listeners hang onto his every word. In this regard, he has just as much in common with legendary country and western songwriters such as Hank Williams, Johnny Cash and Dolly Parton as with his rapping peers.

Next, note how the line “a lad and” is a subliminal reference to the title Aladdin, while the phrase “Wild, Wild East” alludes to Smith’s 1999 hit “Wild Wild West.” Rap music is a narcissistic genre in which artists’ skills are largely judged by the ingenuity of their boasts. In the Aladdin song, Smith triumphantly toots his own horn while never once name-checking himself, which makes him appear both humble and confident. That’s the kind of skill that helped the Philadelphia native nab the first best rap song Grammy Award in 1989.

The Aladdin promo music video harks back to Smith’s 1990s heyday, when he triumphantly sampled old rhythm and blues and TV theme song tunes packed with sentimental value (Aladdin samples Alan Menken’s theme from the 1992 animated version of the Middle Eastern folk tale). Smith’s rap also marks a return to the days when his songs were movie promotions, and it’s tempting to view his lucrative music career as a byproduct of his movie fame: safe-as-milk family entertainment concealed beneath a fashionable urban disguise. Indeed, Smith’s gentlemanly, glad-handing public image contrasts sharply with prevailing rap iconography, which has become so hard-nosed that most rappers wouldn’t be caught dead smiling in their promotional photos.

But a closer inspection of Smith’s music career reveals an artist who gambled on a personal belief in an Afrocentric American dream, one based on ambition, hustle, black pride and monogamy. His decidedly nerdy worldview has drawn its share of hilarious ridicule and attacks from peers, but in hindsight his ’90s hits now seem almost heroic in their contrarian niceness. What follows is an examination of Smith’s music career, an exploration that reveals how he remained true to his principles at the risk of being labeled a corporate sellout … and in the process became one of the best-selling hip-hop artists of all time.

The Plain Brown Rapper

It was 1988, and Smith was bombing.

Better known by his alias “The Fresh Prince,” Smith and musical partner DJ Jazzy Jeff were onstage at the Greek Theatre in Hollywood, California, opening for the Beastie Boys and Public Enemy. At the time, Smith and DJ Jazzy Jeff (real name Jeff Townes) were savoring the success of “Parents Just Don’t Understand,” the breakthrough single from their multimillion-selling album He’s the DJ, I’m the Rapper. They were 19-year-old millionaires, the darlings of radio and MTV. So why were they being jeered on a Los Angeles stage?

Despite their critics, DJ Jazzy Jeff (left) and The Fresh Prince (right) were the darlings of radio and MTV in 1988, savoring the success of their hit song “Parents Just Don’t Understand.”

Photo by Michael Ochs Archives/Getty Images

The reason was simple — Smith and Townes’ set was a disaster. This writer attended that night, and I recall being agog at Smith’s attempts to transform his performance into an interactive experience, appealing for audience participation as he emulated childhood games. Had smartphone cameras and YouTube existed back then, Smith and Townes might have become instant laughingstocks. Compared with the Beastie Boys’ beer-swilling rowdyism and Public Enemy’s fist-thrusting black militancy, Smith and Townes’ slapstick performance was embarrassingly naive and out of touch.

Other rappers might have taken the hostile crowd response as a cue to change course toward an edgier sound. But not Smith and Townes. They seemed creatively beholden to the early days of hip-hop, when the scene was dominated by boogie-down jams such as “I Can’t Live Without My Radio” and “Big Mouth.” As hip-hop legend William “Flavor Flav” Drayton told MTV in 1999: “I remember rap music. We used to party and dance off of it.”

But the dancing came to an abrupt halt in 1988. It was the final year of Ronald Reagan’s presidency, an eight-year term that saw black communities devastated by a federal escalation of the war on drugs. Nationwide, African American neighborhoods had watched in dismay as a blighting influx of crack cocaine gripped the areas where they lived. In mostly black South Central Los Angeles, police were using military-grade weaponry to confront young black suspects, while East Coast neighborhoods such as Roosevelt, New York, went from middle-class prosperity to abject desolation. “Mostly every household had somebody that was strung out,” said Public Enemy producer Hank Shocklee. “Even my brother had a brief moment being addicted, so it resonated very close to me.”

As if in response to Reagan’s hard-line conservatism, hip-hop got deadly serious. Hard-core rap subgenres that had been gestating underground suddenly began garnering widespread radio and consumer attention. Whether it was the political hip-hop of Public Enemy, the desperado “gangsta rap” of N.W.A. and Ice-T or the Afrocentric “conscious rap” of Gang Starr and the Jungle Brothers, 1988 marked a paradigm shift. Just as the Beatles proved rock music could make broader sociopolitical statements, rap’s Class of ’88 seized on hip-hop’s thematic potential, sowing the seeds of a musical revolution.

Into this chaotic musical fray entered Smith. His initial recordings helped transform rap into a lucrative crossover genre, yet he was already at risk of becoming a has-been. In 1989, he and Townes issued yet another collection of teen-targeted novelty tunes entitled And in This Corner …. The album and its spinoff singles flopped. “It was a tragedy,” Smith recalled in 2018. “[The album] went, like, double-plastic.”

The LP’s failure sent Smith into a downward spiral. Like many nouveau riche overnight successes, he had blown through his fortune while neglecting to pay his taxes, and now the IRS was knocking. “Being famous and broke is a s—– combination,” he would later say, “because you’re still famous and people recognize you, but they recognize you while you’re sitting next to them on the bus.”

Then, fate intervened. Hoping to keep his career afloat, Smith began appearing on The Arsenio Hall Show, a new late-night talk show that was an instant hit with the MTV generation. Backstage during one of his appearances, Smith was introduced to Benny Medina, who along with entertainment legend Quincy Jones was developing a sitcom about his childhood experience growing up with a wealthy Hollywood family. Smith aced his audition, and within months of its 1990 premiere, The Fresh Prince of Bel-Air was the top-rated sitcom of the year.

In one fell swoop, Smith was rescued from near irrelevance, and he would make the best of his second chance. Cautiously embarking on a movie career, he earned all-important Hollywood cred by starring in acclaimed, low-budget art house films such as Six Degrees of Separation and Where the Day Takes You. He was craftily starting with modest projects, methodically inching his way up the Hollywood ladder, demonstrating the shrewdness that would make him a megastar.

Triumph of the Will

It had been years since the sales disappointment of And in This Corner…, but now it was 1991 and Smith was appearing on a talk show touting the imminent release of his first single of the new decade. “May 20, we’ll be premiering our video,” he earnestly told Byron Allen. “We’ve been away for a while, and we’re coming at you spankin’ new.”

Will Smith (left) and Benny Medina (right) attend the premiere of Disney’s Aladdin at El Capitan Theatre on May 21 in Los Angeles. A chance meeting with Medina helped launch The Fresh Prince of Bel-Air, which changed the trajectory of Smith’s career.

Photo by Kevin Winter/Getty Images

The music video Smith alluded to was “Summertime,” a mellow head-bobber that deviated from the madcap mold of previous Fresh Prince/Jazzy Jeff tunes. Featuring a “slightly transformed” sample of Kool & The Gang’s seductive ’70s jam “Summer Madness,” Smith’s retooled version perfectly captured the soulful essence of a midsummer day in the ’hood.

“The temperature’s about 88
Hop in the water plug just for old time’s sake
Break to ya’ crib, change your clothes once more
Cause you’re invited to a barbecue that’s starting at 4
Sitting with your friends cause y’all reminisce
About the days growing up and the first person you kiss
And as I think back makes me wonder how
The smell from a grill could spark up nostalgia …”

Call it a comeback. “Summertime” dramatically reversed Smith’s flagging musical fortunes, selling more than 1 million copies and nabbing the Grammy for best rap performance by a duo or group. But for Smith, the single’s importance went beyond accolades and peer honors. “Summertime” seemed to establish a template for the rapper’s subsequent singles. He would eventually part ways with Townes, embarking on a solo career in which he would apply his rhymes to samples of R&B radio favorites from the post-Motown era, including tracks by Luther Vandross, Stevie Wonder, Sister Sledge, Roy Ayers Ubiquity and others.

His music evinced a sense of elegance and upward social mobility. While he wasn’t above sampling the occasional gutbucket stomp, his biggest singles were assembled mostly from R&B songs produced north of the Mason-Dixon Line, lavish funk hits that lent his music the upscale appeal of a Versace collection. Perhaps the best example of this was “Gettin’ Jiggy Wit It,” the gold-certified hit from Smith’s high-stakes 1997 solo debut album, Big Willie Style. The tune sampled “He’s the Greatest Dancer,” the disco classic that name-checks elite clothing brands such as Halston, Gucci and Fiorucci.

Smith’s musical choices couldn’t have been more perfectly timed. He was launching his solo career in the late ’90s, a period of tremendous economic growth and conspicuous consumption. To underscore the notion that he was a musical status symbol, he crammed Big Willie Style with broadly appealing, expensive-sounding samples. “Men in Black” appropriated Patrice Rushen’s luxurious ’80s shuffle “Forget Me Nots,” while subsequent singles “Miami” and “Just the Two of Us” borrowed from The Whispers’ “And The Beat Goes On” and Bill Withers’ satiny 1981 ballad “Just the Two of Us.” Yet, while his tony, aspirational music matched your Cartier ensemble, Smith’s songs were still down-home enough to be played at the neighborhood block party.

His music may have conveyed sophistication, but his lyrics were pure, old-fashioned hip-hop egomania. Big Willie Style found Smith boasting constantly about his boffo film career while flipping off his detractors (“Player haters been hatin’ all my playin’ for years / Now they seein’ they worst fears as I bathe in cheers”). Yet despite all his Tarzanlike chest-thumping, Smith was careful to promote himself as hip-hop’s resident straight arrow. Where his gangsta rap rivals were dismissing women as “b—-es” and worse, the females in Smith’s songs were “ladies” and “hot mamis.” He trumpeted the joys of fatherhood and celebrated his romance with soon-to-be wife Jada Pinkett (“Finally found a person, worthy of all / Instead of pushin’ me down, you want to cushion my fall / Your eyes could make the sun rise, all the birds sing / Seal it with a kiss, bind it with a ring”).

While his tony, aspirational music matched your Cartier ensemble, Smith’s songs were still down-home enough to be played at the neighborhood block party.

This reconciliation of bravado and gee-whiz humility is classic Smith, and he would be rewarded handsomely for his bluster. Boosted by its status as the theme song from the Smith movie of the same name, “Men in Black” topped singles charts throughout Europe and Australia, capturing the 1998 Grammy Award for best rap solo performance. By the time its initial sales run was through, Big Willie Style had moved 9 million copies, making it one of the best-selling hip-hop albums of all time. In the midst of gangsta rap’s blood-splattered heyday, Smith was topping the charts with obscenity-free songs about clubbing, chivalry … and himself.

Seizing on the momentum of his blockbuster performances in movies such as Independence Day and Bad Boys, Smith released his second solo album in 1999. Willennium spawned the debut single “Wild Wild West,” another movie tie-in featuring a sample of Stevie Wonder’s percolating single “I Wish.” The follow-up single “Will 2K” was built from The Clash’s 1983 funky post-punk classic “Rock the Casbah,” while “Freakin’ It” bummed its beat from Diana Ross’ ritzy disco classic “Love Hangover.” Though not quite the sales bulldozer its predecessor was, Willennium nonetheless penetrated Billboard‘s Top 5 and sold more than 5 million copies.

It doesn’t take an Einstein to see that Smith was trading on musical nostalgia to make his songs broadly appealing, but was that so bad? He had already proved with his movie career that he was a shameless, crowd-pleasing capitalist, so why would his music goals be any different? Black songwriters such as Rushen, Nile Rodgers and Kool & The Gang certainly weren’t complaining about Smith’s sentimental hip-hop — his samples were plumping their bank accounts. He was so good at tapping prime funk hits that an associate of mine described him as an “archivist,” a man who heedfully selects stylish baby boomer jams, then gently contemporizes them for posterity (and lucrative Gen X consumption). Asked about Smith and others sampling his songs, Kool & The Gang’s Robert Bell said, “We feel honored! People are listening to our music.”

Will Smith (left) and Tommy Lee Jones (right) in a scene from the film Men in Black in 1997. Smith’s single “Men in Black” captured the 1998 Grammy Award for best rap solo performance.

Photo by Columbia Pictures/Getty Images

But while millions were buying into Smith’s retrograde rap, others were calling him out. It was rumored that he didn’t write his own songs, although Smith’s collaborators attested to his lyric writing/composing skills. Others attributed his musical fame to his soaring movie career, while others criticized him for trafficking in “nonstop pop-rap clichés.” Worst of all, hip-hop purists viewed him as the grievous poster child for corporate rap, exhuming crossover R&B classics to stroke MTV and Top 40 radio programmers. “Just because a song was fun when I was a kid doesn’t mean the guy who made it isn’t a bit of a crossover clown and has made some of the most embarrassing singles of all time,” wrote one contributor on an online forum.

Comments like these would dog Smith throughout his heyday, making him one of rap’s most controversial artists, and you’d still be hard-pressed to find a hip-hop artist who drives purists crazier. Rap music had always prided itself on salting wounds, whether through its automated, minimalist sound, its uncompromising political stances or its embrace of outlaw stereotypes. But then along came Smith with his “nice, clean rap,” and some folks became unglued.

He was resented for not buying into the myth that black hooliganism is somehow authentic (or “real,” to use the parlance of the ’hood). Smith had chosen to become a symbol of the black middle class, a millions-strong group of gainfully employed, law-abiding African Americans who paid their taxes, maybe attended church on given Sundays, and preferred Calvin Klein and FUBU to gangbanger bandannas. His sampling of opulent funk was a subtle shout-out to a black bourgeoisie the media largely ignored. “It’s real important to have balance of the imagery,” Smith told Billboard magazine in 2005. “Yes, there are people who fire guns in the street, but there’s also doctors who go to work in those areas to feed their children.”

But Smith’s critics were raising even broader questions about crossover and hip-hop’s plagiaristic roots. Why was it a crime for Smith to tap the sentimental value of old funk and pop tunes? After all, The Sugarhill Gang established the cannibalistic rules for hip-hop in 1979 when they executed a verbatim lift of Chic’s “Good Times” for their tune “Rapper’s Delight,” the first rap tune of any consequence. Moreover, amid current debates about cultural appropriation, were rap acts such as Smith, Run-D.M.C. and Public Enemy conducting artistic larceny when they sampled white rock bands such as The Clash, Aerosmith and Slayer? Or were these and other rappers simply flipping the bird at segregationist radio programmers who persisted in compartmentalizing white and black music? Whatever the case, it seemed Smith was being held to a harder standard than many of his peers.

His detractors didn’t seem to take into account that sampling is a statement. During hip-hop’s hypercompetitive golden age, the best rap acts used samples partly as a way to align themselves with certain musicians, philosophies and movements. When Dr. Dre heavily sampled Parliament-Funkadelic on his 1991 magnum opus The Chronic, he was establishing an attitudinal connection between his own laid-back jams and George Clinton’s weed-scented stoner funk. Similarly, Smith’s appropriation of post-Motown R&B seemed like a rational choice, an honest reflection of his middle-class upbringing.

The son of a refrigeration engineer and a school administrator, Willard Carroll Smith II was a Baptist who attended a West Philly Catholic middle school. By all accounts, his was a grassroots upbringing that had little, if anything, to do with hoodlums and black militancy. He was 12 years old when his devoutly Christian grandmother discovered a book of his rhymes, many of them peppered with vulgarities. “Dear Will,” she wrote inside the notebook, “truly intelligent people don’t have to use words like this to express themselves. Please show the world that you’re as smart as we think you are.”

That scribbled rebuke changed Smith. “She made me realize that I wasn’t creating only for me,” he said in 2016. “The things I created were going to have an effect on her and were going to have an effect on everyone who came into contact with my artistry.”

Smith took his grandmom’s advice, and if one examines his music, one will discover a positivist philosophy encapsulated by the title track of his 2002 album Born to Reign:

“I believe in God, I believe in destiny

Not destiny in the sense of all of our actions being predetermined

But destiny in the sense of … our ability to choose who we are, and who we are supposed to be …”

He had molded himself into a massively popular polymath entertainer, a man so sure of his rapping dominance that he flamboyantly christened the 2000s the “Willennium.” His hip-hop future seemed bright and unstoppable.

Then he faded from the music scene.

The smartest dude

In 2005, after a three-year absence, Smith returned to the recording fold with an album entitled Lost and Found. Its cover featured Smith at the make-believe intersection of “West Philly” and “Hollywood” streets, an image that suggested he was at a musical crossroads. That notion was underscored by new songs in which he ditched his vintage funk samples for original beats. Although it spawned the Top 10 single “Switch,” the album ultimately sold 500,000 units, not even close to the performance of his multimillion-selling 1990s CDs.

Though he hasn’t released an album in nearly 15 years, Smith hasn’t vanished into obscurity. To the contrary, he’s leveraging his fame to become a digital influencer. He recently used his Instagram account (30 million followers and counting) to hawk branded merchandise, including a sold-out limited run of Fresh Prince of Bel-Air accessories. More than 5 million subscribers visit his YouTube channel to keep up with him and his family. Smith’s songs are still played across the broad spectrum of African American life: at the club, at parties, at backyard barbecues and family get-togethers. Get a real gangsta liquored up enough and he might confess that Smith jams like “Gettin’ Jiggy Wit It” and “Miami” are on his personal mixtape.

Smith is 50 now, and as he enters the elder statesman period of his career, his legacy seems more wide-ranging than many would imagine. He exists as a genre unto himself, a rapper whose austere lyrics and uncomplicated samples are unique in hip-hop. Although he’s never confessed to such, he was a pioneering black nerd well before the empowering phrase “blerd” was even coined. He played a role in unseating rock ’n’ roll as the favored music of youth worldwide, then helped raise rap music’s international stature by becoming a multimedia megastar.

He recently made a surprise guest appearance at Coachella, arguably the world’s most popular and lucrative music and arts festival. Popping onstage during his son Jaden’s performance, the old man reportedly stole the show, lending credence to his lifelong theory that nice guys finish first. “I’m trying to present … a more sound approach to survival,” he said in 2005. “It’s a more long-term approach based on intellect and skills that can’t be taken away from you.

“The smartest dude survives the best.”

Bruce Britt is an award-winning writer and essayist. He lives in Los Angeles with his three dogs and his Fender Stratocaster guitars.