Like future co-stars Martin Lawrence, Eddie Murphy, and Norm MacDonald, Dave Chappelle entered the movie business via standup comedy. Born in Ohio and raised in Washington, D.C., Chappelle studied acting at D.C.'s Duke Ellington School of the Arts and honed his skills as a laid-back yet socially attuned comic in the city's clubs. After making his movie debut as one of the merry men in Mel Brooks' Robin Hood: Men in Tights (1993), Chappelle concentrated primarily on his comedy career and appeared regularly on late night and cable television. He returned to films with small yet key parts in two summer blockbusters: as a comic who helps spoil a date for Murphy's rotund scientist in The Nutty Professor (1996) and as a manic inmate aboard the hijacked convict plane in Con Air (1997). Hitting his movie stride in 1998, Chappelle co-wrote and starred in the prison/pothead caper Half Baked (1998), played a randy schemer in Woo (1998), and revealed that he could also play it (somewhat) straight as Tom Hanks' best friend in Nora Ephron's popular romantic comedy You've Got Mail (1998). Maintaining his dual professions, Chappelle turned a cameo role as Lawrence's former criminal partner into a full-fledged supporting turn in Blue Streak (1999), co-starred with MacDonald in the ill-received Screwed (2000), and returned to Washington, D.C., and HBO with his special Dave Chappelle: Killin' Them Softly (2000).
Chappelle had better luck with his next film, the blaxploitation spoof Undercover Brother (2002). As the B.R.O.T.H.E.R.H.O.O.D.'s terminally paranoid agent Conspiracy Brother, Chappelle was a hilariously twitchy comic highlight in the hit-or-miss satire; Undercover Brother became a small hit amid the summer blockbusters. Chappelle's cutting humor could also be heard on TV that same season, with Chappelle lending his voice as a prank caller to Comedy Central's ribald puppet "reality" show Crank Yankers (2002). His characters on that show were a hit with audiences in search of a hearty laugh, and the following year Comedy Central gave the comedian his own series - the aptly titled Chappelle's Show. Perhaps one of the most controversial series - comedy or otherwise - to hit the airwaves in recent memory, Chappelle's Show offered searing social commentary while frequently pushing the boundaries of good taste. With sketch subjects including a blind black man who - not realizing his true race - heads the Ku Klux Klan and collaborators including former Sanford and Son writer Paul Mooney, the series frequently courted controversy much to the delight of its loyal legions of fans.