Among the greatest moments of Chappelle's Show was the recurring series Charlie Murphy's True Hollywood Stories. In one sketch, Chappelle becomes the mysterious, ruffle-shirt-wearing Purple One. Ten years later, Prince released the album Breakfast Can Wait, and the cover features Chappelle's character holding a plate of pancakes. The two always had one of the funniest friendships in entertainment.
And in a new interview with CBS This Morning's Gayle King, Chappelle tells a story about why he respected Prince so much as a person. It has to do with a guitar pick, Chappelle's sister, and Prince's random act of kindness.
Along with the Prince story, Chappelle—who's on the eve of his return with a three-part Netflix stand-up special—opened up about why he fled to South Africa in 2005.
"I was talkin' to a guy… he basically said to me that comedy is a reconciliation of paradox," Chappelle said. "And I think that that was a irreconcilable moment for me. That I was in this very successful place, but the emotional content of it didn't feel anything like what I imagined success should feel like. It just didn't feel right."
After the immense success of Chappelle's Show, the fame had gotten too much. "But Chappelle's Show's like breakin' up with a girl and you still like her. But in your mind you're like, 'That b**** is crazy. I'm not goin' back,'" Chappelle said. "Fame is a horrifying concept when it's aimed at you, you know? At the end of the day ... you don't have that much control over it. You just try to conduct yourself as best you can."
He went on a sort of walkabout, traveling the world and talking to people and learning and thinking. Like some comedy version of a kung fu movie, Chappelle cleared his head, focused on his health and family. He sounds like a sort of philosopher now, saying that he had conflicts with Comedy Central's corporate environment.
"I fought the network very hard so that those conventions could come to fruition," Chappelle said. "So, like the first episode I do, that black white supremacist sketch. And it's like, 'Well, that's 10 minutes long. It should be five minutes long.' Why should it be five minutes long? Like, these types of conventions. I fought very hard. … So when I watch Key & Peele and I see they're doing a format that I created, and at the end of the show, it says, 'Created by Key & Peele,' that hurts my feelings."
