Is Dave Chappelle insane? The short answer is no. Here's the long answer.
For most people, all they see is the $50 million. I must admit that this is all I see, but Chappelle had opportunities to sell out long ago. It isn't about money but artistic direction. Since reading interviews with the man and such, I've gotten an idea as to why he pulled his disappearing act, and why he is reluctant to return and fulfill the commitment he made to Comedy Central to do a third season of his show.
To understand Chappelle, you must understand why he is so funny. The secret to his success is racial humor. Like it or not, the man got to where he was by doing what all white people recognize as "nigger jokes." Prior black comedians like Richard Pryor, Eddie Murphy, the Wayans clan, and Chris Rock have all edged into this territory, but none embraced it as much as Chappelle did. Dave Chappelle got popular by using the stereotypes of his own race as fodder for his comedy. The same show done by a white comedian would have resulted in a large outcry by both the black and the general community as being racist and probably would have been pulled by the network.
Chappelle's comedy has primarily appealled to white people while making black people a bit uneasy. Though they can make such jokes amongst themselves, they are justifiably concerned when it is disseminated for white consumption. Dave Chappelle makes black people look bad. He can't tell you this because this would require a public repudiation of his work. So, he is caught in a bit of a dilemma. I base this upon Dave's claim that he got to thinking about all of this when he saw a white cameraman laughing a bit too hard at the material Dave was doing.
The reality is that a Ku Klux Klan member would have little trouble watching some of Dave's material and getting a laugh from it. From beginning to end, black people are portrayed on Chappelle's Show as being criminals and drug addicts. His two most popular sketches involve a drugged up black celebrity (Rick James) and a crackhead (Tyrone Biggums.) Lesser characters like Tron also continue the stereotypes.
So, where does this leave Dave Chappelle? Here are his two options:
1. Collect the $50 million and keep doing his song and dance for the man which made him so popular.
2. Collect the $50 million and change his act which would mean not being funny anymore.
Dave is in a bit of a fucked up situation. It wasn't a problem when he was a relative nobody in the world of comedy. Now, he is in a situation that even I don't envy. Sad to say, much black entertainment that goes mainstream ends up being a bit of the Steppin Fetchit routine. Old shows like Good Times and The Jeffersons went this route as black people began to make cariacatures of themselves. If you want to know why JJ's dad disappeared and JJ became the focus of GT, now you know. It was the return of the minstrel show.
Much of this stuff could be hurdled if black people could get beyond racial collectivist thinking. But they can't. It was never Chappelle's intention to be so popular among white people by appealling to their sense of racial stereotypes much as it is not Jeff Foxworthy's attempt to appeal to Yankees' sense of Southern stereotypes. It just ended up that way.
I don't have a solution to Dave's imbroglio. I can see where the man needs time to think all this through, but people never give you time to reflect and get your mind right. I know this myself. What I can say is that you should never ridicule anyone or anything without having some sense of a personal philosophy to go by. This is what the creators of South Park have. Much of their worldview reflects my own which is largely libertarian and skeptical. Since they have this worked out, they do not run into the same self-doubts that Chappelle runs into. Plus, they aren't a one trick pony like Chappelle is. They skewer everyone including themselves. Chappelle is pigeonholed as merely a black comedian doing the race thing. I don't see him ever doing jokes about Muslims, the Iraq mess, North Korea, Jesus, or what have you.
I think Dave will get his mind right, but he will no doubt disappoint someone in the process. Welcome to fame, my man. It is a real bitch.
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