The ‘80s had Eddie Murphy; the ‘90s had Chris Rock; the millennium had Dave Chappelle. The DMV great, who’s been performing stand-up since he was 14, combined some of Murphy’s comedic acting ability and Rock’s raw political insight with his own incisive social commentary to become undoubtedly one of this century’s most revered comedians. Introduced to many as a witty, scrawny dude pantomiming biting a penis off on HBO’s Def Comedy Jam, Chappelle spent the ’90s killing it as a late-night show guest; appearing in The Nutty Professor, Con Air, Forrest Gump, and cult classic Half-Baked; and brought in the new decade with his excellent HBO special, Dave Chappelle: Killin' Them Softly.
It’s enticing to be the contrarian that argues Chappelle has so much more to offer outside 2003 and 2004. You’d be right, but anyone who doesn’t put Chappelle’s Show at the center of his legacy is kidding themself. Dave’s masterpiece created pop culture moments at an insane rate—the R. Kelly spoof, the Player Hater’s Ball, Clayton Bigsby, and Tyrone Biggums all appeared in the first season alone, and that wasn’t even the show’s best.
But Chappelle’s Show made its star too famous. Chappelle had to contend with a mainstream audience possibly laughing at his jokes—many of which dealt with the surreal nature of being a black man in America—for the wrong reasons. Chappelle has specifically pointed to a skit in which he’s a blackface pixie who convinces black people to act stereotypically. One white man’s laugh during the bit threw him off. "When he laughed, it made me uncomfortable," Chappelle told Time. "As a matter of fact, that was the last thing I shot before I told myself I gotta take f****** time out after this. Because my head almost exploded."
So Chappelle’s Show had to go, and Dave spent the better part of last decade out of the spotlight. But he bounced back when he was ready, booking multi-night residencies at Radio City, dropping four Netflix specials in a $60 million deal with the streaming service, and hosting his first Saturday Night Live. From now back to his prime, and in honor of his 45th birthday, here are the best Dave Chappelle bits.