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.
It's the classic tale of Robin Hood ... reenvisioned by comic master Mel Brooks. As evil Prince John (Richard Lewis) oppresses the people, Robin (Cary Elwes) steals from the tax collectors, triumphs in an archery contest, foils (literally!) the Sheriff of Nottingham (Roger Rees) and makes goo-goo eyes at Maid Marian (Amy Yasbeck). The titular musical number, involving song, dance -- and, yes, men in tights -- is an undisputed highlight.
- You've Got Mail
- The Nutty Professor
- Blue Streak
- Con Air
- Undercover Brother
- Chappelle's Show
- Richard Pryor: I Ain't Dead Yet #*%$#@!!
- Def Comedy Jam: Vol. 1
- Best of the Larry Sanders Show
- Dr. Katz: The Complete Series
- Half Baked
- 200 Cigarettes
- Dave Chappelle: For What It's Worth
- Inside the Actors Studio: Dave Chappelle
- Dave Chappelle's Block Party
- Beef 4
- Comedy Central's Home Grown
- High Times Greatest Hits
- Just for Laughs: Stand-Up: Vol. 3
- Richard Pryor: Omit the Logic