I’m so glad that this essay exists, and even more content to believe that Dave Chappelle is out there, possibly very happy, not crazy, having made a deliberate decision to step away from his brilliant comic achievement (and all that cash).
Toward the end of Chappelle’s Show I remember getting more uncomfortable with the sketches and how far over the line they were willing to go for no reason. What started out as go-tell-all-your-friends insightful and hilarious ended as no more than head-shakingly embarrassing and irritating. To me, the wit had turned into spite. After reading this, I can only guess I wasn’t the only one who felt that way. You only have one life to live, what are you going to do with it?
Like Salinger’s retreat from fame, Chappelle’s departure demanded an explanation: how could any human being have the willpower, the chutzpah, the determination to refuse the amount of money rumored to be Chappelle’s next paycheck: fifty million dollars. Say it with me now. Fifty. Million. Dollars. When the dust settled, and Chappelle had done interviews with Oprah and James Lipton in an attempt to recover his image and tell his story, two things became immediately apparent: Dave Chappelle is without a doubt his generation’s smartest comic, and the hole he left in comedy is so great that even ten years later very few people can accept the reason he later gave for leaving fame and fortune behind: he wanted to find a simpler way of life.