Dave Chappelle is mostly known for being a stand-up comedian who had his own show—a sketch comedy television series called Chappelle's Show (2003–2006). He created it with another comedian, Neal Brennan. The show ran for two entire seasons and the third season contained of three episodes of previously unreleased sketches.

The comedian didn't want to continue with the series because he wasn't content with himself and he imagined success differently. Also, the job was very intense and he didn't have time to do anything beside work. The feeling was so strong that even $50 million didn't convince him to stay in the show. The contract was already there, the sum written, but Dave Chappelle walked away.