Dave Chappelle’s 5 Best Characters

After eight years away from standup, Chappelle returns to headline the Oddball Comedy & Curiosity Festival.


At the peak of his career Dave Chappelle left it all behind. After eight loooooong years away, he returns to the stage for Funny or Die’s comedy bonanza featuring laughmakers like Flight of the Conchords, Hannibal Buress, and Demetri Martin. There’ll be psychics too.

Sure, the lineup is stellar, but the main draw is Chappelle–partly because of his iconic humor, partly because of the morbid curiosity about celebs who fall from grace. Will he be able to regain the momentum and shake off recent awkward appearances and unruly hecklers? We hope so. At his zenith of his career Chappelle was something to behold. Here’s a refresher course on his five greatest characters:

Verizon Wireless AmphitheatreSeptember 15

5. Dave Chappelle as Prince

4. Dave Chappelle as Lil Jon

3. Dave Chappelle as Silky Johnson, “Player Hater of the Year, 2002”

2. Dave Chappelle as Clayton Bigsby, black white supremacist

1. Dave Chappelle as Tyrone Biggums

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