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Chappelle was the show's co-writer, co-producer and singular star.
The show combined the pop-culture instincts of early Saturday Night Live, the satiric inventiveness of the Ben Stiller Show and the racial daring of In Living Color. The sketches on Chappelle's Show poked fun at new-school stars like Lil Jon and R. Kelly and old-school stars like Samuel L. Jackson and superfreak Rick James.
One sketch imagined a "racial draft" in which multiracial figures like Tiger Woods had to pick a race. Another featured a send-up of MTV's Making the Band, in which P. Diddy dispatches would-be pop stars on increasingly ridiculous tasks ("Walk uptown to the Bronx, and get some breast milk from a Cambodian immigrant!"). And one of the show's most electric characters appeared on the first episode: a blind white supremacist who doesn't realize he's black.
The show worked because it talked about what America finds difficult to talk about: race. As mixed-race marriages multiply (Chappelle's wife is Asian) and more kids check "Other" on census forms, the racial conversation may be getting even more difficult. Racial divisions are becoming more complex, harder to understand, more challenging to discuss. That's where Chappelle comes in. He takes all those hang-ups about race and lifts them up, spins them around, puts them in our face. Deal with it. Laugh at it. But don't ignore it.
"[Chappelle] illumines the idiocy, the sheer lunacy, of racial bigotry," says cultural commentator Michael Eric Dyson, author of the new book Is Bill Cosby Right?, "while also fearlessly pointing the finger at black folks' loopy justifications of questionable black behavior. He's great at taking particular events, episodes and escapades and using them to show America the unvarnished truth about itself."
But as the late rapper biggie smalls once observed, mo' money, mo' problems. In August 2004, after Chappelle's big deal was announced, people started calling him a genius a lot more. They started laughing at the wrong jokes for the wrong reasons at the wrong times. And to his mind, the show became more like working at Wal-Mart, although for a much higher salary. But he kept on with it. Says Chappelle: "Fifty million dollars is a lot of money. And what I'm learning is I am surprised at what I would do for $50 million. I am surprised at what people around me would do for me to have $50 million." Although news of the deal was heavily reported, the conflicted Chappelle didn't actually put his name on the pact until last March. Says Chappelle: "I was thinking for the longestI'm not even gonna sign this s___."