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The Misunderstood Legacy of Will Smith’s Music Career

The man formerly known as the Fresh Prince won the first rap Grammy, but is rarely looked upon as an impactful artist these days. His evolution in hip-hop is more interesting than he’s given credit for.

Jay Torres

This Sunday, Peacock will premiere the first episode of Bel-Air, a contemporary, dramatic reimagining of the beloved ’90s sitcom The Fresh Prince of Bel-Air. To mark the occasion, The Ringer is looking back on the legacy of the original series and the influence of the star who defined it, Will Smith. This is a story all about how pop culture got flipped, turned upside down. Welcome to Fresh Prince Day.


“Will Smith” means “movie star.” It’s been a couple decades since “Will Smith” last meant “rapper,” and it’s been 10,000 years since “The Fresh Prince” signified something other than a classic sitcom in perpetual syndication. To this day we call O’Shea Jackson (who?) Ice Cube. The same goes for Ice T, Queen Latifah, and LL Cool J. What about the Fresh Prince? The first rapper to win a Grammy? What do we make of the three consecutive decades when Will Smith ranked among the biggest rappers on the planet?

His earliest songs—“Parents Just Don’t Understand,” “Girls Ain’t Nothing but Trouble,” “A Nightmare on My Street”—were cool but they were also a bit corny. DJ Jazzy Jeff was a virtuoso with priceless musical innovations, such as the transformer scratch, to his credit. But the Fresh Prince always seemed a bit disengaged from the more competitive postures and movements in contemporary hip-hop. Even the meathead LL Cool J wanted to be the best in addition to being the biggest; the Fresh Prince just wanted to be the biggest. His ambition made for a contrarian outlook. It was proudly suburban. It was explicitly swear-free. It was weirdly unburdened by “top five, dead or alive” standards. These weren’t songs for the streets. These were songs for the mall. This was bottle service for the ball pit.

It’s easy for anyone younger than Funkmaster Flex to listen to hip-hop from the 1980s and hear nothing but rough experimentation until Paid in Full, Bigger and Deffer, and Criminal Minded, each released in 1987. The genre had spent a decade learning to speak. On “Summertime,” the Fresh Prince mimics Rakim and succeeds despite the obvious discrepancies; Rakim’s voice was rich and dark while Smith’s voice, even at its lowest, was always just about to crack. He also often mimicked LL Cool J, on “Charlie Mack (The First Out the Limo),” for instance, but as a lighter, scrawnier figure. Here he is, in his early-’90s transition from the Fresh Prince to Will Smith, lifting the semi-auto flow from Das EFX. It’s not uncommon for rappers to borrow popular flows and it’s always fun to discover that a rapper once took a very different approach to the mic before they blew up: Ice Cube echoed the Beastie Boys before he cofounded N.W.A; Jay-Z rather notoriously “used to rap like the Fu-Schnickens” before he recorded with Foxy Brown and the Notorious B.I.G. Will Smith was still constantly searching and transforming a decade and several awards deep into his rap stardom. He was hip-hop’s Peter Pan.

He never grew up but of course he blew up on the strength of his ability to move kid’s meals for Burger King. For half a decade or so, Will Smith’s rap crossover appeal was a bewildering force in American life. He was at once a marginal movement, compared to Aftermath, Bad Boy, and Cash Money, and yet a tremendous commercial breakthrough for hip-hop in his own right. Will Smith split into his own parallel universe. He had Eve on Willennium, but he and Eve never really existed in the same physical dimension, you know? These songs played on the same programming blocks and these rappers shared studios, yet the idea of Smith’s Columbia Records labelmate Nas ghostwriting a bit of Big Willie Style struck so many rap fans—at the time possessing a lower tolerance for ghostwriting in hip-hop—as an urban legend.

In his solo career Will Smith cornered the market on “jiggy rap.” His biggest hits in this phase—“Gettin’ Jiggy Wit It,” “Miami,” “Will 2K,” “Wild Wild West”—exemplified the common argument against that whole style of production, popularized by Puffy and the Trackmasters: Their beats were too simplistic, too dance-oriented, and they barely even bothered to reimagine the primary samples. The Trackmasters produced “Men in Black,” the musical theme for the movie and the lead single from Big Willie Style, flipping Patrice Rushen’s post-disco classic “Forget Me Nots” with Smith’s relentlessly on-brand raps about “extraterrestrial violence.” By the mid-1990s this was a common sort of selling out—Mase rapping for The Rugrats Movie; LL Cool J, Busta Rhymes, and Method Man role-playing the Monstars for Space Jam—but more than anyone Will Smith rehearsed the PG-13 soundtrack gesture and made it his signature. “Miami” is a banger about club life in South Florida and somehow Will Smith childproofed even that. This commitment to corniness—this transcendence, dare I say—culminates rather absurdly in “Wild Wild West,” a big, ridiculous R&B hoedown in cross-promotion for the notorious summer blockbuster flop costarring Smith and Kevin Kline.

In his music, Will Smith also developed a conspicuous dadcore sensibility. On Big Willie Style he covered “Just the Two of Us,” rapping three verses about his first son, Trey, and thus transforming the original into a different kind of love song. It’s a simple flip and a bit too sappy (“101 Dalmatians on your CD-ROM”) for my taste. But this is the essential ingredient in his best songs, too: his willingness to sound a bit silly in comparison to his peers. He’s always moved to extreme corniness, but with a steady hand. That was his superpower. He didn’t overthink his credibility. He didn’t doubt his capacity to send an old R&B standard back to the top of the charts. Grover Washington Jr. and Bill Withers peaked at no. 2; Will Smith sent his cover of “Just the Two of Us” to no. 1 in the rap charts.

But of course Will Smith, with his blockbuster designs on everything, hit his tipping point and then inevitably succumbed to overproduction. “Black Suits Comin’ (Nod Ya Head)” from Men In Black II; “Switch” and “Party Starter” from Lost and Found—the beats got too chunky and the flows got too choppy for the Fresh Prince to pull off. Trackmasters fell out of fashion. Timbaland and Pharrell flooded the radio with edgier crossover rap for the rest of the 2000s. I keep finding ways and excuses to once again call Will Smith “corny” but perhaps I mean “normal.” For all his profits and costumes and accolades, Will Smith was a startlingly normal dude. He was soft and he was spectacular and he had Dru Hill, Kool Moe Dee, and Stevie Wonder looking altogether foolish in the promotional campaign for the worst movie I’ve ever seen in a theater. He made this look easy. He made this look good.