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.
In this valentine to modern romance, book superstore magnate Joe Fox (Tom Hanks) and independent book shop owner Kathleen Kelly (Meg Ryan) fall in love in the anonymity of the Internet -- both blissfully unaware that he's trying to put her out of business. Director Nora Ephron's Golden Globe-nominated romantic comedy puts romance on the ropes -- and forces two people to make tough decisions about life, love and livelihood.
- Robin Hood: Men in Tights
- Con Air
- Half Baked
- Dave Chappelle's Block Party
- The Nutty Professor
- Dave Chappelle: For What It's Worth
- Inside the Actors Studio: Dave Chappelle
- Undercover Brother
- Chappelle's Show
- Richard Pryor: Omit the Logic
- Dr. Katz: The Complete Series
- Blue Streak
- 200 Cigarettes
- High Times Greatest Hits
- Best of the Larry Sanders Show
- Richard Pryor: I Ain't Dead Yet #*%$#@!!
- Def Comedy Jam: Vol. 1
- Beef 4
- Comedy Central's Home Grown
- Just for Laughs: Stand-Up: Vol. 3