While continuing to work on his live act, Chappelle managed to land a few key supporting roles -- as the cruel comic making fun of Eddie Murphy in The Nutty Professor (1996) and as a manic convict in Con Air (1997). In 1998, Chappelle co-wrote and starred in the pothead caper film Half Baked and played Tom Hanks' best friend in the romantic comedy You've Got Mail.
Chappelle's popularity has grown tremendously thanks to his 2000 HBO stand-up special, Killin' Them Softly, and the 2003 debut of his sketch comedy series, "Chappelle's Show," on Comedy Central.