In 2005, Dave Chappelle was the biggest star in comedy. In the realm of cultural significance, Chappelle’s Show reigned supreme, his characters and skits spawning endless memes and impersonators. It was impossible to get away from, and it solidified Chappelle as a celebrity. Then, just like that, it was gone. Chappelle had inexplicably departed to South Africa, and production on the show ceased. It was the end of an era, and for some time, the public was at a loss as to what had occurred and why.
Eventually, the truth came out: the comic had left the show after Comedy Central offered him a whopping $50 million to do a third and fourth season. It was an unimaginable decision for many, and Chappelle wasn’t talking. He maintained a low profile for many years, resisting calls for an explanation.
Finally, in 2014, he reemerged on the Late Show With David Letterman, to promote a series of shows at Radio City Music Hall. Letterman predictably pressed Chappelle, who was initially evasive on the matter before answering, “Of course…of course, I would have liked to have that money.”
He continued, “You know, because when you quit, like my friends will try to make me feel better, but no one has been through that, so they’ll say… 'You know, Dave, at the end of the day, you still have some integrity.’ That’s great. I’ll go home and make the kids some integrity sandwiches!”
“There’s nothing anyone can say,” Chappelle added. “You do what you feel like you need to do at any given time.”
Later, in 2017, Chappelle would go on to do a rare interview with Gayle King, where he would go into more detail about the controversial decision.
He explained that leaving the show came from a realization that success was nothing like he thought it would be.
"I was talking to a guy, and he basically said to me that comedy is a reconciliation of paradox. I think that that was an irreconcilable moment for me, Chappelle said. “That I was in this very successful place, but the emotional content of it didn't feel like anything I imagined success should feel like. I just didn't feel right."
When asked whether he would have done things differently, he expressed, "It's very hard to say what you would have done. You only really know what you did. At the end of the day, ultimately I feel good about what I did. It was not easy, and I do not recommend it. But it worked for me. I took the Dave Chappelle detour. It was a scenic route. I'm glad I took the route, but it was a long, long, long detour."
Chappelle said that in the aftermath, he was able to finally find balance in his life by being able to “do what I like to do and avoid some of the parts of it that I was uncomfortable with.” Chappelle noted that he has relationships with his kids, and was able to engage with others differently. He was finally able to rest, to appreciate his life and the places and people around him.
The comic indicated that he did miss Chappelle’s Show, but that a reboot of the popular program is most definitely not in the cards. “Chappelle's Show is like breaking up with a girl and you still like her, but in your mind, you're like 'that bitch is crazy. I'm not going back.'"
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