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 Chappelle’s Show. 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. Chappelle collected royalties from both. By 2004, Chappelle’s Show was the highest-rated program in its timeslot among 18 to 34 year-olds. Gen-Xers and Millennials fueled the show’s home media sales, helping it become the best-selling television series DVD of all time.
Decades into a post-Civil Rights Era where enforced colorblindness threw bleach on the country’s discourse about race, Chappelle exposed the weak threads of America’s proto-post-racial social fabric. 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. Where Chappelle delighted in highlighting the absurd ways in which race is lived in the United States, Obama did his best to smooth them over.
Haunted by the sense that his humor was entrenching America’s racial hierarchy rather than chipping away at it, Chappelle walked away from Comedy Central’s offer of $50 million to produce the third and fourth seasons of Chappelle’s Show, in 2005. He was sorely missed as the years went by, particularly among audiences who desperately wanted someone to spoof the self-righteous liberalism of suddenly anti-racist Obama voters. The tabloid media—biceps still bulging from the grave they dug for Michael Jackson’s reputation in the mid-2000s—fanned rumors that he was addicted to crack. Chappelle did not die in the 2000s as Jackson did: Both have survived, as cautionary tales for Black entertainers about the perils of building too big a tent. If the olive branches we extend will one day be used to flog us, perhaps its best if we kept the peace to ourselves.
More than a decade after Chappelle’s Show went off the air, it’s difficult to overstate its influence. Watching director Jordan Peele’s smash thriller Get Out, I felt the same sense of racial dis-ease as I got from Chappelle’s Show, the cumulative effect of so many in-jokes and on-point observations piled atop fantasies of racial reconciliation, squeezing air and life from our delusions of progress like so much sociopolitical deadweight. As a proxy for class, race is still the foremost indicator of one’s proximity to the American dream; even at the most intimate points of contact between ethnic groups, we’re not as far along as we believe towards making that no longer the case.
As such, prophets like Chappelle are not meant to be popular forever. Their political function as practitioners of parrhesia—the act of speaking truth to power—precludes such longevity. It must. If they’re doing their job as truth tellers, they’ll burn out, suffer social death or cross a line and fall out of favor. Their inevitable rejection is proof of their value. They can try to climb back into the public’s embrace but only at the risk of their own principles. In his two new Netflix comedy specials released on Tuesday, March 21, Chappelle attempts to regain relevance. He succeeds, but for the wrong reasons.
In the first of these stand-up specials, The Age of Spin, Chappelle plays devil’s advocate, building his set around celebrations of Bill Cosby and OJ Simpson in Los Angeles. In the second, Deep In The Heart of Texas, he describes racist repression to a conservative audience in Texas. In the former, he’s in a blue state flirting with being red; in the latter, he’s in a red state with a case of the blues. The distance seems a bit much for Chappelle to travel without leaving something behind. 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.
As far as comedic technique is concerned, Chappelle still has few peers. His aural attack of well-timed punchlines, impassioned rants and pitch-perfect accents (nobody does “aggrieved racist southerner” better) is spellbinding. 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 The Confidence-Man—a character who changes his identity from one page to the next: pimp, historian, sports commentator, activist and ultimately comic. This is 21st-century Americana.
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. Here we are in early 2017, and the jokes of the most visible comedian in the country are incessantly on gays, on survivors of sexual assault, and on less fortunate Blacks. As Chappelle talks about shirking a benefit trip to Flint, Mich., in order to attend the Oscars, we should wonder what happened to the guy who made a political statement by holding a big Black block party in the middle of a rapidly gentrifying section of Brooklyn.
Is it we who’ve grown out of the hijinx of Chappelle’s Show, which history will reveal as immature? Or has Chappelle himself betrayed the brilliance of his early-career achievements by regressing into that which he once parodied the most—a bigoted buffoon afraid of change? “You gotta Google shit I lived through,” he tells a Millennial in the audience.
The second set contains more laughs on a moment-to-momentum basis, even if it isn’t as structurally as ambitious as the first. Though nearly hijacked by a bizarre story of a fictitious blackmail, Chappelle offers several gems. “Isn’t it amazing that this disease happens to hate everybody that old white people hate?” he asks of HIV/AIDS. 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. So Chappelle seems to have weaponized his grudges against the people he imagines are out to take his spot. College-age audiences of Chappelle’s Show probably never thought they’d live long enough to see Dave become the Black Archie Bunker.
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. Chappelle finds a hero in Simpson, building his set around four separate encounters with The Juice. But the success that Chappelle admires in Simpson is incredibly fragile because it hinges on the whims of White sympathies and approval. Insecure about his place in the eyes of audiences he once confronted with reckless abandon, Chappelle lashes out at other groups (gays, transvestites, Jews) who are trying to steal the “racial hot seat” from Black Americans in the “discrimination Olympics.”
In the sociopolitical obstacle course that Chappelle describes, one needs to suffer in order to have social relevance, so that one can then broadcast the act of overcoming suffering. Retracing overlapping oppressions can produce great observations: “You were in on the heist, you just didn’t like your cut,” he says of White feminists who pretend to be warriors for social justice. But in these specials, Chappelle often reaffirms conservative tendencies that we remember him rebelling against. These days, his comedic gifts come at a considerable price to him and his audience. Accept them if you like. But you’ll want to keep track of the receipts.