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He was invited to appear regularly on many late night television shows as well as to do stand-up specials on cable television. His movie career was also picking up as he was offered parts in the blockbuster hit The Nutty Professor in 1996 and Con Air in 1997. Though the parts were small, it was clear that Chappelle's comedy had great potential for growth. Chappelle was ready to take his place in the spotlight. He co-wrote and starred in Half Baked in 1998. The film helped him become better known, especially to a young audience. Also in 1998 he costarred in the comedy Woo and the romantic hit You've Got Mail with Tom Hanks. Chappelle landed a supporting role in the 1999 cop comedy Blue Streak, playing Martin Lawrence's former partner in crime. He continued concentrating on his film career into the new century with the 2000 release Screwed.

Also at the turn of the century, Chappelle returned to his home town of Washington D.C. to perform in his own HBO comedy special, Dave Chappelle: Killin' Them Softly. Over the next couple of years Chappelle did more stand-up than acting, but Hollywood was not finished with him. In 2002 he starred in Undercover Brother, a comedy that had audiences rolling in the aisles. He also appeared that year as voice talent on the hit Comedy Central show Crank Yankers.

In 2003 Dave Chappelle became a household name when he produced and hosted his own weekly comedy hour, aptly titled The Dave Chappelle Show. Chappelle shines as he combines his two loves, stand-up and acting. The show encompasses all that is good about classical stand-up comedy with the added spice of sketch comedy thrown in. Fans, both young and old, can find something to laugh about in the politically incorrect, socially active, and absolutely hilarious skits that Chappelle writes and stars in. Chappelle is not afraid to tackle the issues in his stand-up routines. The show, featured on Comedy Central, also gives viewers an idea of what Chappelle's live shows would be like.