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Sunday, September 14, 2014 |  Madison, WI: 57.0° F  A Few Clouds
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Dave Chappelle's Block Party

I don't know what's weirder, that I keep watching the first two seasons of "Chappelle's Show," which are currently in eternal rotation on Comedy Central, or that the damn skits keep making me laugh. "I'm Rick James, bitch!" Why hasn't that line bored me to death by now? Before he pulled his infamous disappearing act, abandoning the show in the middle of taping the third season, Dave Chappelle was cooking up some of the raciest race-based humor since "In Living Color," which pales in comparison. Richard Pryor himself said that Chappelle was his rightful successor, thereby passing over Chris Rock, who'd been polishing the throne so long he must have forgotten how to sit down. (Translation: He just isn't that funny.) But Chappelle has a Hamlet-like ambivalence about being declared the new King of Comedy. How do you poke fun at the powers that be when you've just signed a $50 million contract?

One way: by making movies like Dave Chappelle's Block Party on the side. Filmed on Sept. 18, 2004, eight months before Chappelle headed to Africa, this Woodstock-like documentary, which preserves for posterity an afternoon-to-evening hip-hopalooza that Chappelle put together on the streets of Brooklyn's Bedford-Stuyvesant neighborhood, has to be just about the coolest thing he could have done with the power and influence he's accumulated. And don't be fooled by the title. Dave Chappelle's Block Party is indeed a block party, with musical entertainment provided by the likes of Kanye West, Mos Def, Dead Prez, Erykah Badu, Jill Scott and the Roots (with Big Daddy Kane). But it's also, like Woodstock, a vision of a community united in its love of a good time, even during bad times. The message amidst the revelry: Fight the power.

We open in Yellow Springs, Ohio, which Chappelle calls home, his father having taught at Antioch. It's three days before the concert, and Chappelle's already drumming up an audience, handing out tickets good for a bus ride and free lodgings. It's a utopian gesture, one of the tickets going to the elderly white woman who runs the convenience store that keeps Chappelle in cigarettes. Later, he invites the entire Central State University Marching Band, many of whom haven't been to New York City. Throughout the movie, Chappelle interacts with people he's never met before, effortlessly locating the humor in whatever situation he happens to find himself in. But race is never far from his mind. "How many white people does it take to screw in a light bulb?" he asks a group of musicians. "None, 'cause they'll get a nigger to do it."

That sounds pretty crude in the retelling, but Chappelle knows just how to put it over, with a delicate blend of mock and genuine anger. He can be quite hard to pin down, as evidenced by his recent appearances on "Inside the Actor's Studio" and "The Oprah Winfrey Show." That hipster smile can harden into a withering frown in the blink of an eye. But compiling the greatest show on earth ' "the concert I've always wanted to see," he calls it ' brings out the best in him. And the musicians respond in kind. Dead Prez bring down the house with a rousing rendition of "Turn Off the Radio." And Lauryn Hill, reunited with the rest of the Fugees, uses Roberta Flack's "Killing Me Softly With His Song" to kill us with hers. And presiding over it all is Chappelle, deftly juggling the roles of impresario and emcee, star and fan, King of Comedy and Court Jester.

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