Joe Rogan told Dave Chappelle his decision to leave his Comedy Central sketch show at the height of its success in 2005 was “one of the most gangster moves in the history of entertainment.” Chappelle sat down with Rogan for an interview on the JRE podcast episode #1647 in May 2021. Rogan told Chappelle, “It made you a legend.”
Chappelle said, “What was so remarkable when I walked away from the show was it was against incentives. People couldn’t understand it at the time. ‘It was so much money, how could you do that?’ And blah, blah blah blah. But you know if I had taken that money and finished that show, I would’ve got the money, but I might never have been the same.”
He continued, “I was geared a certain way growing up, because I wanted to make it in show business. And boy that s*** fell all the way apart. And as far as I knew my career was over. … I didn’t see anyone else do this and get back up. And the drumbeat is, ‘he’s crazy, he smokes crack, he’s this and that,’ it was a wild experience. The way people close to you react to it. Like I had failed or I had ruined my life. And when you’re cold, that phone don’t ring that often. And I had over a decade of sitting in that choice. But I didn’t languish in that experience, I started doing standup for much better reasons than making it. I still enjoyed it.”
Rogan added, “But the way you did it was so cool. You kind of drifted off.” Chappelle said, “I promise I wasn’t trying to be cool. It was a series of troubleshooting.”
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Chappelle Said Going Back on the Road to do Comedy Shows Brought Him a New Perspective He Needed
Chappelle said when he went back on the road to do stand-up shows he started to see the world and experience the places he was traveling to for standup shows, instead of just flying in for his set and then leaving. Rogan told him, “If you set aside some days to do things, that’s very valuable for your perspective. It’s valuable for your act. It’s valuable for everything.”
Chappelle said, “You learn things, you gain perspective, which is very vital for a comedian and a person. It’s humbling and empowering at the same time. … Any information is valuable. I call it the expense of knowledge. Your buddy that’s a war veteran or something. You don’t want to know the s*** he knows if you knew what he had to do to know these things. I would not recommend quitting your show the way I did, if you can avoid it.”
He said about leaving the show, “I learned a lot. It was a humbling experience. I had young children, I was raising my kids. I was living a suburban life. And then every once and a while I’d get this feeling, like, ‘I’m the funniest guy, I gotta get out there.’ … At one point I had done one of these big comedy tours that Live Nation had put together. I wiped out in Hartford and it was all over the internet. It was the first time that type of thing had happened to me. But for the most part the tour went good. But it was a tough tour for me. It was a long show, I had to close it. My chops weren’t as tight as they normally were. I didn’t suck by any means. It could’ve been better. But it made me want to go back.”
Rogan Told Chappelle He Is the ‘First Guy to Beat the System’
Rogan and Chappelle also talked about his recent settlement with ViacomCBS over Chappelle’s Show. Chappelle urged his fans to stop watching the show, saying it was “stolen goods,” because of longstanding licensing and royalty issues. Those were resolved in 2021.
Chappelle said in an Instagram post in February to his fans, “You made that show worthless because without your eyes, it’s nothing. And 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.”
Rogan told Chappelle, “Congratulations. You’re the first guy to beat the system. You’re the first guy to get f***** over by the system, go public with it and then get your money. I’ve never heard it happen before. I don’t think it’s ever happened before.”
Chappelle, shouting out ViacomCBS executive Chris McCarthy for his help, said, “I still can’t wrap my mind around it. … It was amazing. I can say with a high degree of honesty, not to say I was never angry about it, but I don’t think I was ever bitter. … The bottom line is no matter what happens to you, you’ve got to keep going. Bitterness is quite cumbersome. Jokes is a way of shaking that off or processing something with the alchemy of levity.”
Chappelle added, “t wasn’t a court of law. I don’t believe I would have got anything in a court of law. But I think in the court of public opinion it was a good thing for me to say my piece. And through the years, it wasn’t something I would harp on. It was something I was actually reluctant to talk about. … If you look at life, anything in life, through the framework of money, you’ll miss most of the picture.”