Dave Chappelle went on the Late Show With David Letterman last night for one of his only interviews in years (there was the one with a Minneapolis television station, and another on San Francisco radio). He talked again about why he abandoned Chappelle's Show, what exactly he gave up when he did and whether he regrets doing so.
The clip above—edited by the Late Show—is at times tense. Letterman doesn't immediately laugh at Chappelle's jokes, and when Chappelle talks seriously about the time surrounding his crisis you can almost feel the air in the Ed Sullivan Theatre thickening. He is still defending himself, and though Chappelle has moved on, his interview with Letterman made it clear that the public hasn't. Seven years hasn't bought Chappelle understanding.
His demeanor, at least, was relaxed—he flashed his still-recognizable rascal grin often. He was also candid. When Letterman asked him if he regretted turning down "this enormous sum of money," Chappelle said, "It's very hard to go through something like this because no one's really done it before. There's not too many people who don't think I'm crazy, right?"
But he ended, nonetheless, with a joke. "I might be happier," he said, talking about giving up somewhere in the range of $40 million. "I don't know. There's no way of knowing. But sometimes I listen to a Jay Z record and it starts to make me feel bad about some of the choices I made. This guy's had more fun in two songs than I've had in the last 11 years."