12 Best Characters From Chappelle’s Show

There are comedy shows that are funny in their moment, and then there are shows that permanently change the language of pop culture. Chappelle’s Show firmly belongs in the second category. When Dave Chappelle and Neal Brennan’s sketch series premiered on Comedy Central on January 22, 2003, it mixed celebrity parody, racial satire, Hip-Hop culture and completely ridiculous premises in a way television had rarely seen before.

The series also helped transform Chappelle from a respected stand-up comic and familiar movie face into one of comedy’s biggest names. More importantly, its best sketches refused to choose between being smart and being absurd. Chappelle could use one character to dissect racism and another to spend five minutes screaming three words at strangers, and somehow both could become classics.

That versatility gave Chappelle’s Show a ridiculous bench of memorable characters. Some appeared repeatedly, others only needed one legendary sketch, and a few were Chappelle’s exaggerated versions of real celebrities. More than two decades later, people are still quoting them. Here are 10 of the best.

Clayton Bigsby

Introducing Clayton Bigsby in the very first episode told viewers immediately that Chappelle’s Show was willing to go places most television comedies would not. Chappelle played a blind Black man raised to believe he was white who becomes a committed white supremacist, turning an outrageous premise into a sharp satire about how racism is learned.