After beginning his film career in 1993 as Ahchoo in Mel Brooks‘ Robin Hood: Men in Tights, he landed supporting roles in box office hits including The Nutty Professor, Con Air, You’ve Got Mail, Blue Streak and Undercover Brother. His first lead role was in the 1998 comedy film Half Baked, which he co-wrote with Neal Brennan. Chappelle also starred in the ABC TV series Buddies.
In 2003, Chappelle became more widely known for his sketch comedy television series, Chappelle’s Show, also co-written with Brennan, which ran until his retirement from the show two years later. The show continues to run in late-night syndication and on television networks around the world. By 2006, Chappelle was called the “comic genius of America” by Esquire and, in 2013, “the best” by a Billboard writer. In September 2017, Chappelle was awarded an Emmy Award for his guest appearance on Saturday Night Live.