Dave Chappelle’s inexplicable departure from Chappelle’s Show — and a hefty $50 million contract with Viacom — hangs over everything he does. Walking away from a massively successful television show, flying to Africa, and disappearing from the entertainment industry for 12 years is quite a thing to live down. Some people are forever branded with the details of their infamy — Bill Buckner’s error in the World Series, Ashlee Simpson lip-syncing on Saturday Night Live, Kanye interrupting Taylor. Chappelle carries the brand, but he’s maintained the mystery around it.
And so one of the more interesting parts of the comedian’s New Year’s Eve stand-up special drop, The Bird Revelation, comes at the end, when he gives the intimate audience in the Comedy Store’s Belly Room (and the audience sitting at home) a tiny bit of insight into his disappearance from Hollywood in 2005, by recounting a story from Iceberg Slim’s book, Pimp: The Story of My Life.
The Iceberg Slim story revolves around a sex worker at the natural end of her career, and her pimp, who goes to great lengths to force her, his best earner, into further years of indentured servitude. He stages a death and pins the blame on her, the guilt and shame breaking her spirit. Only her pimp can offer her salvation, and the only way to repay that debt is to keep working.
It’s natural to want to decode what Chappelle is trying to say, to apply literal meaning to what is, in essence, a parable about power dynamics and the cruelty of capitalism. In his analogy, Viacom and Comedy Central are the pimp, going to extreme lengths to prevent their best earner from attaining true freedom. Chappelle is the put-upon sex worker, incapable of giving any more, but having no choice. This fits nicely with the way Chappelle characterized his decision earlier in the special. He was a victim, and his choice to quit was heroic. (He even makes a point of telling the audience that people often call him a hero to his face.) In the story, the sex worker doesn’t quit. She carries on with her pimp, thanks to the pimp’s deception. People she believed were helping her were really working to further the lie that she killed a man. The dead man that she mourned was another part of the trick, used to prey on her humanity. But who, in this analogy, was the dead man that almost dragged Chappelle deeper into the Hollywood system he seems to alternately despise and crave approval from?
Well, it’s not a perfect analogy, but Chappelle is the dead man. What he killed was a part of himself, as he pandered to the mainstream and reached for the giant payday; as he gave white audiences the cover to laugh at edgy racial material without understanding the history or the pain behind the jokes. He didn’t do it alone, though. The system he so loathes — the studio heads, the agents, the middle managers, the white writers, like Chappelle’s Show co-creator Neal Brennan, the white fans he was asked to cater to — were, in his mind, the ones that pushed him to make a show he wasn’t proud of anymore. It was inadvertent, but once Chappelle realized it, it played a role in his decision to quit.
So unlike the sex worker, Chappelle saw through the ruse. (Also unlike the sex worker, his idea of being used is being given $50 million to make white people laugh.) Instead of getting deeper in, he got out, and now, in 2018, he’s free. He can tour, he can drop Netflix specials, smoke inside, and provoke modern notions of social justice as he sees fit. He’s still rich (he’s quite fond of mentioning he drives a Porsche), but not the kind of rich that makes one beholden to CEOs or stockholders. There are no overnight ratings for his specials, no benchmarks to hit. No quarterly earnings report hinges on his participation.
Now he’s free, or at least it seems like he is. But that white audience is still there, and in Equanimity, Chappelle acknowledges he needs that audience to survive. “If there were no white people here tonight, I might leave this bitch with $1,800,” he says toward the end of the special. The cruelest part of the pimp’s trick, after all, is that the sex worker believed she was making her own decisions, that the choice to stick with her pimp was her own, that she was free.