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Dave Chappelle as Prince / Image by Lia Kantrowitz 

Chappelle's Show's Musical Acts Were a Hell of a Drug

Jeff Weiss

Jeff Weiss

Sketches featuring Dave Chappelle as Prince, Rick James, and Lil Jon—plus televised performances by Kanye West, Erykah Badu, Big Boi, and more—are still influencing pop culture today. In other words, "Game, blouses."

Dave Chappelle as Prince / Image by Lia Kantrowitz 

By any conceivable rationale, Prince's iconography and mystique should have been fixed and absolute by 2004. He was arguably the most transcendent musician of the previous 30 years: a globally adored movie star who re-defined gender, shades of color (purple), meteorological phenomena (rain) and classic American muscle cars (the Corvette). But such was the sheer comic genius of Chappelle's Show that it altered the public myth of the late Minnesota legend, nearly two full decades after the first purification rituals in Lake Minnetonka.

There's a high likelihood that the Prince of your imagination is not actually Prince but rather Dave Chappelle as Prince, ensconced in a ruffled velvet Zorro costume, reverse dunking and hanging on the rim while taunting Eddie and Charlie Murphy. "Game…blouses." But not only did Chappelle's Show confirm and expand the superhuman qualities long suspected of the Purple One, it completely rebranded the concept of the pancake. That's true impact. It's one thing to amplify your already rarified esteem for the man who wrote, "Kiss," it's an entirely different achievement to make you think differently about one of the most iconic breakfast foodstuffs of the last century. Even Prince concurred, later using Chappelle's impression as the cover art for the single, "Breakfast Can Wait."

Prince's single cover for "Breakfast Can Wait"

The greatest music show of all-time happened to be a sketch comedy program. The runners up aren't even that close. The Chris Rock Show was the closest analogue and even booked several of the same musical guests a half-decade prior, but its cultural impact feels comparatively muted. In Living Color was hilarious and groundbreaking, but parodies of Vanilla Ice and Snow can't rival Charlie Murphy's stories of thrashing Rick James. That's what you get for grinding filthy cowboy boots on a brand-new suede coach purchased with Coming to America money. For the sake of our already frayed sanity, we're lucky that no accurate accounting exists for how many people have snorted a key bump and reflexively chortled, "cocaine is a helluva drug."

You can point to any number of television shows that booked exceptional musical guests: The Muppets, MTV Unplugged, Rap City, Yo! MTV Raps, Arsenio, Ed Sullivan, The OC, Beverly Hills 90210 (to quote Steve Sanders on The Flaming Lips, "I've never been a fan of alternative music, but these guys rocked the house.") But none could mix Chappelle's Show's blend of incisive satire and subtle racial critique, definitive parody and gross-out humor, good taste and imaginative musical direction, political lampoons and "'Pac is still alive" gags.

It offered the perspective that could only come from a hip-hop obsessive—one who grew up immersed in the culture and suddenly became one of its most integral components. In the pilot, Chappelle proclaims his love for "the hip-hop music" and defends it against media scolds who indicted its materialism and misogyny. It segues into an obscene sketch about Nat King Cole spraying champagne all over a sequined nightclub chanteuse and hollering "King Cole Records" like he was Birdman in 1999. If that didn't answer questions about what and who he was representing, Dead Prez's "Hip Hop" opened every episode.

Alongside comedy and Spike Lee movies, hip-hop initially bonded Chappelle with his show's co-creator and co-writer, Neal Brennan. A native of Chicago and Philadelphia, Brennan became enamored with the genre when he first heard Public Enemy's "Bring the Noise" as a teen. Within a few years, the aspiring comic was penning articles for The Source's comedy issue.

"When we wrote the pilot, we were just watching Lauryn Hill Unplugged over and over and over," Brennan remembers. "That whole show was such a raw plaintive cry and it was definitely poured into the Chappelle's Show DNA."

Its genius didn't necessarily stem from surrealist whimsy, but from its funhouse warping of reality. The Prince and Rick James sketches actually happened. The R. Kelly "Piss on You" song was rooted in actual court reports. Wu Tang Financial was ridiculous but not unthinkable. Chappelle and co-creator Neal Brennan intuitively understand how to exaggerate the natural absurdity of pop music's characters, while Chappelle had a brilliant knack for mimicry, comic timing, and catchphrase—the legatee to Richard Pryor, Eddie Murphy, George Carlin, and Chris Rock. In the history of the English language, only Too Short can coax more musicality and humor out of the word "bitch" than Dave Chappelle.

"Chappelle's Show defined a culture and made it cool to be socially conscious and explore and question what you see," says Big Boi, whose performance of "The Rooster" ranks as one of the show's most memorable.

When asked to select his personal favorite music sketch, the West Savannah-born half of Outkast cited the "Making The Band" spoof. That's another validation of why Chappelle's Show remains timeless while most comedy ages like Eminem punch lines about Chris Kirkpatrick. You don't have to have seen Diddy's short-lived MTV reality show to find Dylan spitting "hot fire" funny. When someone asks for your Top 5 greatest rappers list, you are still guaranteed a cheap laugh by responding, "Dylan, Dylan, Dylan, Dylan, Dylan." If nothing else, Chappelle's bulging eyes, antic gestures, and Marx Brothers-caliber slapstick sells every sketch.

"He spoofed current events, but the comedy had layers and a deeper truth to it," Big Boi added. "He didn't seek out the biggest artists, but he looked for the ones that were dope and put them in interesting settings."

Dave Chappelle as Lil Jon

Debuting in 2003, Chappelle's Show emerged towards the tail end of the underground boom, but the comic had quietly been a part of the Soulquarian scene for years. He initially met his current manager Corey Smyth (who also manages Vince Staples and Chad Hugo) at a De La Soul and Talib Kweli concert at Kenyon College in the late 90s.

Through a serendipitous twist of circumstance, Chappelle and Smyth reconnected in the Village one evening. The former breezed by on his skateboard about to do a set at the nearby Comedy Cellar on Macdougal. While Smyth talking on the phone on a corner outside Electric Ladyland Studios, killing time between the now-canonical sessions that featured The Roots, Talib Kweli, Common, D'Angelo, Erykah Badu, Mos Def, and J Dilla. Within a few months, Chappelle was doing Nelson Mandela and Rick James impersonations on the Reflection Eternal album (Kweli was then-managed by Smyth). After Comedy Central green-lit Chappelle's Show, it was inevitable that he turned to Smyth to book the musical guests.

"We developed a pitch to artists where we said that we didn't want them to do their single," Smyth says. "We wanted them to pick a B-Side or something that didn't necessarily have label support, so that they'd have the opportunity to create a music video or find the ideal landscape to perform the song."

As you'd expect, Comedy Central initially found their choices too underground. The corporate Wish List was comprised almost exclusively of crossover artists with Top 10 chart hits. By the second or third meeting with the network, Smyth hadn't successfully booked a single act.

"Dave told me let's just book our friends…book your crew," Smyth remembers. "I was like, 'are you sure they're going to be cool with it? He was like, 'they'll be fine.'"

Dave Chappelle as Rick James / Image by Lia Kantrowitz

The first musical guest remains among the most indelible. Mos Def and Dave drove around Harlem while the original Pretty Flaco nimbly spit bars that would've forced Dylan to include him in his Top 5. The entire concept of Carpool Karaoke springs from here.

If you run down the list of subsequent musical guests, the talent assembled is staggering: Busta Rhymes, Big Boi, Killer Mike, Badu, Slum Village, The Roots, Wyclef Jean, Blackstar, De La Soul, DMX, Ludacris, Cee-Lo, Common, Kanye, and Snoop Dogg. Season's Three's musical guests included Nas performing with his father Olu Dara at the Cotton Club, The Beastie Boys performing on the Staten Island Ferry, and Eminem and Proof. None of these segments ever aired and presumably are moldering in a Comedy Central archive waiting for divine excavation.

"Every musical performance gets degraded on TV," Brennan says. "I rarely watch musical performances on SNL but when I'm there in the studio it's inevitably riveting, so something happens—you can't feel the bass in your chest when it's on TV. Sports and comedy travel well, but live music almost never does. We tried to lesson that degradation by putting it in a different context."

In the cases of some of those performances, the live version became the only version we remember. Kanye and Common's televised rendition of "The Food" was the one that wound up on Be.

"As soon as Kanye got on set, he was like 'why are we shooting in front of the fireplace. The song is called 'The Food.' We should be shooting it in the kitchen," Smyth says. "It was about making the artists feel comfortable doing what they were doing. They started cooking in the kitchen and it was dope."

It's been nearly a decade and a half since the show's influence became so ubiquitous and overwhelming that Chappelle famously walked away from Michael Jordan money, lest he deal with frat bro's screaming, "I'm Rick James, bitch" at him for the rest of his life. You can't blame him. Those catchphrases and caricatures are irrevocably seared into our consciousness. He refracted the myth into something weirder and funny, but somehow even more true to the artists.

Before Chappelle, most people pigeonholed Lil Jon as a monosyllabic crunk rapper. Of course, the recurring sketches mined that reputation for laughs, but also found him periodically switching into a dignified scholarly voice ("How's that sandwich coming?") The contrast made the jokes funnier, but also tacitly underscored the furtive intelligence of the former Morehouse University business student—the side that didn't fit into the one-note pop culture cliché.

People initially watched because it was funny. We continue to revere it because nothing has come remotely close to replacing it. Chappelle's Show riffed on serious realities of race, sex, inequality, politics, and the preposterousness of pop culture, but never forgot Oscar Wilde's famous adage: if you're going to tell the truth, be funny—or else they'll want to kill you.

In the process, it defined an era of music and helped usher a constellation of stars into the major commercial arena. Maybe someone like Common would've wound up a movie star and racked up number one albums without the boost he got from appearing on Chappelle's Show, but it's unquestionable that the success of the latter proved that it was possible to blow up without compromise. Like all the best comedy, there was an ineradicable honesty at its core—one that obliterated lines between underground and mainstream, what was edgy and what was acceptable, myths and reality, pancakes and whatever mortals eat for breakfast.

Jeff Weiss is a writer based in Los Angeles. Follow him on Twitter.