When most of us met Dave Chappelle in 2003, he was a 30-year-old stand-up with an off-kilter take on race relations, a host of forgettable film appearances and a mandate from Comedy Central to write and star in the television series What followed were two generation-defining seasons of uproarious political commentary that introduced a set of immortal characters to pop culture lore, each as famous for the way they parodied America’s social order as they were for the way they upheld it: a misogynistic Rick James caricature; the minstrel news anchor Chuck Taylor; a Black Ku Klux Klan member named Clayton Bigsby.
Half of the audience laughed at the pathology of these characters; the other half laughed with it. By 2004, was the highest-rated program in its timeslot among 18 to 34 year-olds.
His comedy belonged to the immediate pre-Obama era of the Patriot Act and Hurricane Katrina; to a country that was more diverse than ever, but that did not yet have a politics that reflected the browner America created by the Voting Rights Act of 1964 and the Immigration and Naturalization Act of 1965.
What Chappelle used for comedy in keen skits like “The Racial Draft,” Obama eventually mobilized for politics.
Though nearly hijacked by a bizarre story of a fictitious blackmail, Chappelle offers several gems.
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“Isn’t it amazing that this disease happens to hate everybody that old white people hate? The political content of the second set merges with personal and familial beefs of the first, and the tone of both specials finds Chappelle grappling with his own exceptionality as a Black man who “makes it” and retains resentment at having to work twice as hard to do so.In the last stretch of the first special, Chappelle caps a mesmerizing summary of mid-century American history with the jarringly hilarious observation “and during that whole time, Bill Cosby raped 54 people.” At an elevated level of technical wizardry, these skills become transcendent, and the parallels for Chappelle’s gift of gab are not to be found elsewhere in standup, but in music and literature.Like a jazzman without a horn, Chappelle’s code-switching routine moves from profound to profane, reflecting the local idioms and vulgarities of the great American vernacular.As a narrator, Chappelle is the elusive, nameless protagonist of Herman Melville’s 1857 novel —a character who changes his identity from one page to the next: pimp, historian, sports commentator, activist and ultimately comic. Chappelle’s content is another story—no less intricate and complex than his delivery but with far less of the redeeming universalism.Chappelle draws sharp political lines in the sand, and it’s often oppressed groups who are made to eat dust.It’s fitting that OJ Simpson is the first set’s patron saint.It was Simpson whose “exceptional Negro” persona ingratiated him into White households in the racially acrimonious 1960s and ’70s.His pensive stare in the special’s opening sequence—voiced over by Morgan Freeman and laced by whirling camera moves straight out of a Scorsese-esque character study—connotes both contemplation and confusion.A captive in a comedic climate he helped construct, Chappelle is an inmate of expectation, flailing—and at times failing—to be free.So Chappelle seems to have weaponized his grudges against the people he imagines are out to take his spot.College-age audiences of probably never thought they’d live long enough to see Dave become the Black Archie Bunker.