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Why Hip Hop Needs Another Chappelle’s Show

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It’s been ten years since Chappelle’s Show first aired on Comedy Central, and in its brief run of two seasons and three “lost episodes”, it became regarded as an all-time great among sketch comedy programs. The show garnered major acclaim for its keen social commentary on prejudice and black culture – in his final months, Richard Pryor remarked that he had “passed the torch” to titular comedian Dave Chappelle. In spite of this, Chappelle backed out of his show in the middle of filming the third season, citing long work hours, the relatively shoestring budget, and the sensation that his audience was “not smart enough” for his material.

Comedy Central has inevitably tried to repeat its success – every new show they’ve put black comedians at the helm of post-Chappelle (all two of them) has been compared to their former flagship. Their inability to regain their former audience isn’t for lack of trying – efforts like Key and Peele and the totally forgettable Chocolate News were formulated, branded, and promoted to an African-American audience with all the subtlety we’ve come to expect from Viacom, the same media giant that’s been neutering MTV for years. What did Chappelle’s Show pull off on its limited budget that millions of corporate dollars haven’t been able to recreate in its wake?

I’d wager that the biggest difference is Dave himself, who aside from being easily one of the best stand-up performers of his time was truly tuned in to hip hop music and culture, not to mention well acquainted with some of the biggest acts of the time. Between 2003 and 2004, while most primetime and late night comedy television was devoted to recycled jokes about the upcoming election and Michael Moore, Chappelle’s Show was busy lampooning the spread of rap promo videos, the R. Kelly sex tape, and the fact that white people didn’t have any idea what “skeet skeet skeet” meant until it was far too late.

Parody being the sincerest form of flattery, many artists returned the favor of being lampooned on the show with guest appearances. Though its legacy has been diminished as the go-to impression for college guys everywhere, the line “I’m Rick James, bitch!” stems from a first-person account of the R&B idol’s 80’s excesses by cast member Charlie Murphy as corroborated by Rick James himself. Lil Jon, whose career is nearly synonymous with the “A Moment In The Life Of Lil Jon” sketch, made an excellent cameo along with Chappelle’s famous caricature. Even network TV darling Wayne Brady got involved in the “Wayne Brady Show” episode as an orchestrated response to Paul Mooney’s jab that he “made Bryant Gumbel look like Malcolm X” in a moment of self-aware brilliance.

Perhaps the musician who contributed the most to Chappelle’s Show was Mos Def, who appeared multiple times, seemingly as a de facto cast member. His roles as gang leader Cornrow Wallace in “The World’s Greatest Wars” and as the representative of the black delegation in “Racial Draft” must have been tightly scheduled into his already busy film career. He also made three appearances as a musical guest including an intimate preview of then-unreleased track “Close Edge” as performed from the shotgun seat of a moving car to an audience consisting solely of Chappelle and two dashboard cameras.

Given the musical performances, in some ways Chappelle’s Show might have been the more hip-hop-oriented spiritual successor to early Saturday Night Live – if you can believe it, SNL was once the sort of place that would invite less-than-mainstream acts like Gil Scott-Heron to perform for an audience of millions. Chappelle’s inspired low-budget staging solutions like filming De La Soul’s performance of “Much More” from inside their tour bus or Common’s “The Food” on a kitchen set are reminiscent of the unusual set pieces NBC would craft for bands in the late 70’s, such as the slime-oozing television adorning Frank Zappa’s performance of “The Slime” or David Bowie’s antics with macabre puppets and a robo-dog.

Modern SNL, on the other hand, could learn a thing or two from Chappelle. In the same year that Saturday Night Live brought in Ashlee Simpson for her famously-flubbed lip-sync performance (and the hoedown heard around the world), Chappelle’s Show sported two of the first major television appearances of then-recent Roc-A-Fella records inductee Kanye West a full year before he’d make the stage at 30 Rockefeller Plaza. Cee-lo Green, who appeared with Chappelle to promote Cee Lo Green… Is The Soul Machine in 2004 wouldn’t get a shot at the NBC stage until 2008 when he scored a hit as one half of Gnarls Barkley with “Crazy” and wouldn’t get a solo slot until “Fuck You” became his surprise mega-hit in 2011.

Considering that SNL was busying itself with Avril Lavigne and Britney Spears at the time, the self-explanatory sketch “Pretty White Girl Sings Dave’s Thoughts” seems like an apt reaction to the musical mainstream. The premise that the only way to get his opinions heard was to have a pretty white girl sing it in a high voice is typical of Dave’s comedy style: a deceptively simple routine that scathingly spotlights societal prejudices. Seeing the aforementioned pretty white girl sing “fuck the police” in a Disney Princess voice goes from cute to cringe-worthy when you realize that N.W.A. has never been on SNL but Taylor Swift has twice.

This isn’t to say that Chappelle’s Show existed in a completely separate universe from its mainstream contender – mutual guests like DMX, The Roots, and Busta Rhymes are no strangers to the 30 Rock stage. Chappelle’s Show also shares with SNL the unfortunate trend of omitting the majority of its musical guests from subsequent broadcasts. Over half of Chappelle’s musical guest appearances are missing from DVD and remain unreleased.

Even so, when you take away the star power and celebrity guests, Chappelle’s unfiltered commentary and observational style of humor alone reveals his deep interest in music. One gets a very clear sense of Dave’s priorities from the sketch “Jury Duty” in which he quips that O. J. Simpson might as well go free if the court system is going to leave the murders of Tupac and Biggie unresolved, exclaiming that “Nicole Simpson can’t rap!”


Chappelle may have envisioned his comedy as what he did instead of music – in an absurdly-embellished autobiography sketch, he reimagines his comedy career as though it were Eminem’s 8 Mile, rapping his jokes to a moshing audience. It’s been said that all comedians want to be musicians and vice versa, although ultimately one will have to choose (unless you’re Wayne Brady). It’s obvious that Chappelle was a comedian first and a musician only if a sketch required it – his extensive outtake reel from the DVD set reveals that he usually just said chanted the word “spaghetti” over and over if he ran out of ideas.

What matters is that Chappelle’s commentary on hip hop and music culture was from knee-deep in it as opposed to the sidelines. Consider HBO’s Mr. Show With Bob And David, another hallmark among sketch programs, and its farce of the East Coast – West Coast rivalry with the premise that ventriloquists had appropriated the conflict as their own. The subject matter isn’t foreign to Chappelle’s Show territory, but the routine comments far more on Bob Odenkirk and David Cross’s position as outsiders to hip hop culture than on the genre itself.

This is what Chappelle’s Show did for hip hop that other comedy programs simply can’t. It’s not as though audiences are completely unaware of the music or culture, but it’s only ever explored distantly by casually acquainted performers. Most comedy programs only address blues, soul, R&B, and rap from the outside looking in, and usually only to make bashful meta-jokes about how little they know. An outsider’s world is not an invalid point of view, but when there are kids whose only exposure to hip hop is the latest “mash-up” they heard on Glee, you have to wonder about Dave’s “pretty white girl” bit. While Chappelle had firm reasons for his split from Comedy Central, the world might have been a better place with more Chappelle’s Show.