Coming to Terms with Dave Chappelle

"The world can’t tell you who you are. You just gotta figure out who you are and be that."

I distinctly remember the only issue of Blender Magazine that I ever read had Dave Chappelle on the cover (August 2004). The mid-00s were the magazine format’s last peak, and there were so many of them, newsstands stretching down grocery-store aisles, colorful covers like cereal boxes. I don’t remember what prompted my purchase of this particular issue, but I read the Chappelle piece with intense interest. I’d seen some of Chappelle’s stand-up and seen him in movies here and there. I’d never seen Chappelle’s Show proper, though I’d watched clips from it online. I had friends who were huge fans though, the kind who couldn’t describe a sketch without devolving into uncontrollable laughter.

The summer of 2004 was just after the second season of Chappelle’s Comedy Central show aired, the very peak of the series. This was before the Big Deal, the third-season delays, the infamous Africa retreat, and ultimately the end of the show altogether. The end of that particular show-business drama had yet to transpire, but something about the article seemed askew. Chappelle said then that what he’d loved about doing the show was that no one was paying attention, which allowed him and his staff to do whatever they wanted. He worried that now that it was a hit, they’d be under more scrutiny and the fun would dissipate. “The show worked because we acted like nobody was watching,” he told Blender’s Rob Tannenbaum. “And now, everybody’s watching.” As I watched the subsequent events unfold, that sentiment echoed in my head. In his Showtime stand-up special from that year, For What It’s Worth, he comments, “I don’t trip off being a celebrity. I don’t like it. I don’t trust it.”

His appearance on Inside the Actor’s Studio on December 18th, 2005 might be the most the most telling of the time. His intelligence has always been evident even in the crudest of his comedy, but it really shone here. Take his thoughts on the term “crazy” applied to celebrities: “The worst thing to call somebody is ‘crazy’. It’s dismissive. ‘I don’t understand this person, so they’re “crazy.”’ That’s bullshit. These people are not crazy. They’re strong people. Maybe the environment is a little sick.” As he told Blender the year before, “The public really enjoys the downfall of celebrities too much.”

Like his forebears Richard Pryor, Paul Mooney, Bill Cosby, and Eddie Murphy, as well as his closest contemporary, Chris Rock, Chappelle’s take on race is highly nuanced and never forgets the orthogonal concern of class. All the way back to 2000’s Killin’ Them Softly in which he is taken unbeknownst to the ghetto in a limo at 3 a.m. and encounters a weed-selling infant. Acknowledging every issue that scenario entails, Chappelle twists it into one of the funniest bits of the set

After his hiatus, he returned in 2017 with four new Netflix specials. Filmed in each of the previous three years, these show a sturdier, calmer comedian, a storyteller with a lost decade’s worth of stories to tell. There are scant set-up/punchline jokes among the laughs. Chappelle’s delivery here owes a lot to Cosby, whom he somewhat backhandedly defends in The Age of Spin (filmed in March of 2016 at the Hollywood Palladium). This bit displays much of the nuance I mentioned earlier. It’s difficult to be this nuanced, to use subtlety to great effect, when everyone seems to want to split issues right down the middle. The critics have already piled on, drawing lines between themselves and Chappelle’s views on the issues of the day.

There is an aspect of speculative design sometimes called “design fiction,” sometimes called “critical design.” Its practitioners basically set out to challenge the hegemony of the present way of thinking about things—buildings, gadgets, objects, whatever. Instead of reifying the currently held ideas, critical design imagines a different way of doing or seeing things. There’s nothing sacred in comedy, except comedy. Comedy is what’s funny. Comedy is what’s true. You don’t have to agree with it. We don’t have agree with all of the comedy that we laugh at. We don’t have to agree with all of the comedians that we love. We have to let comedy do its own brand of critical design. We have to let comedy explore other possible presents. We have to let comedy do what it does. If we don’t, it is doomed. If we continue without it, we are doomed.

Chappelle starts off Equanimity, the first of his two New Year’s Eve specials (filmed in September of 2017 in Washington, DC), claiming to be bowing out again. His mistrust of fame lingers as he cites hitting the comedy jackpot the way he has as a sign it’s time to get out of the casino. Then he makes jokes about how good at it he is—and he is! Making jokes about making jokes is a gamble of a different kind, but Chappelle’s punchlines hit paylines every time. He goes on to address the critics of his last special mentioned above and again deftly illustrates his understanding of the divisive differences between issues of gender and race, as well as race and class. He does a lot of this by splitting the pairings that make odd relationships, from poor white people and rich presidents to the Amish and technology. To be funny is to be good at comedy. To do Chappelle’s level of cultural criticism and be this funny is to be in a rare group of masters. They kill and let live, skewering the worst of the times and making everyone else laugh. That’s comedy’s crowning achievement. And we’re all better for it.

Compared to the others, the last of this spate of specials, The Bird Revelation (filmed in November of 2017 in LA), is a far more intimate affair, in both setting and subject matter. Chappelle illuminates the recent dark days of Hollywood and America, interrogating scandals of all kinds, pushing all the issues past points of comfort, including his own career. He addresses the comedians in the back, calling for them to do the same. “You have a responsibility to speak recklessly,” he says.

Chappelle has continued to speak recklessly, recently taking on the very channel that brought him back. Netflix was streaming his old Comedy Central show without compensating the man. He called them out from the stage, and they pulled the series. Now, it’s back with his blessing. “I never asked Comedy Central for anything,” Chappelle says in a ten-minute clip called “Redemption Song.” He continues,

If you remember I said ‘I’m going to my real boss’ and I came to you because I know where my power lies. I asked you to stop watching the show and thank God almighty for you, you did. You made that show worthless because without your eyes it’s nothing. And when you stopped watching it, they called me. And I got my name back and I got my license back and I got my show back and they paid me millions of dollars. Thank you very much.

Another boon of making power, taking power, and then using it to make more.

At an appearance at Allen University in South Carolina a few years ago, Chappelle said, “It’s okay to be afraid, because you can’t be brave or courageous without fear. The idea of being courageous is that, even though you’re scared, you just do the right thing anyway.” And he told the students at Pace University in 2005, “The world can’t tell you who you are. You just gotta figure out who you are and be that.” He told James Lipton on his show that if he weren’t a comedian, he thought he’d like to be a teacher. I’d say he’s already both.