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Books | Comedy

November 21, 2013

He Was Rick James, Bitch

Jason Zinoman investigates the art and life of Dave Chappelle—and why the comedian's blowup made perfect sense.

justin williams

Chappelle's Show debuted just over a decade ago, and the Comedy Central show quickly established Dave Chappelle as the funniest and most innovative comedian in the country. For two seasons, the sketch show barreled straight through the boundaries of racial comedy, translating into a long-awaited success for its star. Yet in 2005, the comedian mysteriously and inexplicably walked away from his hit and an alleged $50 million contract, eventually settling into the reclusion of family life in the small, progressive town of Yellow Springs, Ohio. Jason Zinoman wanted to figure out why.

Jason Zinoman
Chappelle balked at the charge that stars who have public meltdowns are crazy, adding that maybe “their environment is sick.”

Jason Zinoman

The answers are in Zinoman's recent Kindle Single, Searching for Dave Chappelle. A comedy critic for The New York Times and author of the book Shock Value, Zinoman was riveted not only by Chappelle's curious decision to abandon fame and fortune, but also by his quiet journey back to a national comedy tour this past summer. Revisiting the comedian's earliest and strongest influences, Zinoman uncovered a recurring theme throughout Chappelle's career—this willingness to disappear.

In an email interview with Zinoman, the author discusses the inspiration for his Kindle Single, his favorite Chappelle's Show sketch, and that one theory about Chappelle joining the Illuminati.

Gelf Magazine: When did this idea originate for you, to try and uncover the mystery surrounding Dave Chappelle since he left the show?

Jason Zinoman: The short answer is that Dave Blum from Kindle Singles asked me to do it. But the longer one is that about a year or so earlier, a chat on Twitter about Chappelle made me realize that he’s the one comic alive I most wanted to see perform. That’s partly because I think he’s one of the greats, but also because two seasons of a notorious and beloved show has distorted his legacy to be one of sketch comedy. But Chappelle has always been primarily a stand-up, and as the comedy critic of the Times, I wanted to examine that. And once I did see him, I realized that the mystery of him leaving was not just a show-business question, but also an artistic one, since he uses his exit in his act—magnificently.

Gelf Magazine: Was the plan always to do it as a Single?

Jason Zinoman: Yes. It’s perfect form for it, because it requires more space than a magazine piece, but I don’t think it would have benefitted from a bloated 300-page book treatment.

Gelf Magazine: What was your relationship to Chappelle before you started working on this? Had you ever interviewed him previously?

Jason Zinoman: Never interviewed him, but I’ve followed his career for a long time. We actually have some similarities in our background. We are around the same age and both grew up in the Maryland suburbs and moved to Washington, D.C. for high school, and some of his teachers actually were students of my mother, who ran a theater in the city. I even heard a story about Chappelle’s mother walking out of a play that my mom produced!

Gelf Magazine: The recent incident at his show in Hartford obviously drew a lot of attention to Chappelle and the tour. But I imagine that was a nice turn of events for you and your Single?

Jason Zinoman: Yes! If Dave Chappelle wanted to help me with publicity, I appreciate it! By the way, while I don’t think this was intentional, the episode was good for him too. He got a lot of press for it, but just as important, he had something newsy to joke about onstage.

Gelf Magazine: What is it about Chappelle that sets him apart as a comic?

Jason Zinoman: So many things, but I would say that the foundation of his act is his delivery. He is funny and ingratiating before he gets to the punchline, and once you have that, that frees you up to take all kinds of risks that other comics cannot. And what’s really impressive about Chappelle is he does. He’s willing to take elaborate tangents or push the line in terms of content or say really unlikable things, because he knows deep down, he can win the crowd back in an instant.

Gelf Magazine: What impact, if any, did Chappelle’s Show have on current comedy shows like Key & Peele, Tosh.0, or even something like Louie, where one person is given complete creative control?

Jason Zinoman: I’m not sure I see much influence in those shows. He wasn’t the first to build a sketch show around one personality and he has a partner in Neal Brennan. But I think you see some influence in details like, say, exploiting the talents of Questlove.

Gelf Magazine: Do you have a favorite Chappelle’s Show sketch?

Jason Zinoman: Oh, that’s hard. I love the Racial Draft, Clayton Bigsby, Making the Band and of course all the Charlie Murphy True Hollywood Stories. But if I have to pick a favorite, I will go with the Wayne Brady episode. It’s genius, hilarious satire with a sharp point of view that only he could pull off.

Gelf Magazine: You wrote a lot in the Single about Chappelle leaving the show, and how the more plausible theories surrounding it seem to involve Dave struggling with himself and no longer being the underdog. How much of that do you think was his fear of becoming too popular? And if it was a factor, isn’t that rather prescient in terms of how the culture treats mainstream success today?

Jason Zinoman: I think there really was a bunch of different reasons, and expectations were one of them. I do think he preferred to be the outsider rather than the showbiz star, but this was not a major reason. More significant, I believe, were his own expectations. He had high standards. But he also wanted to be recognized and achieve mainstream success. I think he wanted that big contract, but he also wanted artistic control—and the reality is that those two things are occasionally in tension. It’s instructive to look at Louis CK. He clearly chose control over money, and eventually the money came. But I wonder if Chappelle had taken a much smaller contract that also gave him the leeway to take all the time he wanted to make season three—if he would have been better off.

Gelf Magazine: In the intro, you wrote about briefly catching a glimpse Dave in his hometown of Yellow Springs. Was that the closest you came to speaking with him while working on this? Was there ever a point where you thought you might actually get to talk with him or sit down with him?

Jason Zinoman: No. I never really expected to talk to him, and truth be told, it wasn’t that important to me. Chappelle has given interviews on this subject, so I have a good sense of what he would say. In my mind, the project of this Single was to learn more about him by looking through his past and at his work. I was searching for Dave Chappelle in his childhood in D.C., his early years in the clubs in New York, his trying times in television in the 1990s and in the politics at Comedy Central. The heart of this story was in reporting out these worlds and trying to understand him through the contexts that he emerged out of. In one interview, Chappelle balked at the charge that stars who have public meltdowns are crazy, adding that maybe “their environment is sick.” What I tried to do is follow his lead and look closely at his environments.

Gelf Magazine: Any other big projects that you’re working on or exploring?

Jason Zinoman: Outside of a second child I’m expecting next month, not really. I write a bi-weekly column for the Times on comedy and that keeps me busy enough right now. But I do hope to write another book in a few years.

Gelf Magazine: But seriously, Chappelle leaving the show was all about joining the Illuminati, right?

Jason Zinoman: How do I know you are not part of the Illuminati? You do live close to Chappelle. Hmmm.

justin williams

Justin Williams is an associate editor for Cincinnati Magazine. You can follow him on Twitter at @Williams_Justin.

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Article by justin williams

Justin Williams is an associate editor for Cincinnati Magazine. You can follow him on Twitter at @Williams_Justin.

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