Chappelle moved to New York City to pursue a career as a comedian. He gathered the courage to perform at Harlem's famed Apollo Theater in front of the infamous "Amateur Night" audience. The performance resulted in him being booed off the stage. Chappelle has described the experience as the moment that gave him the courage to continue his show business aspirations. He quickly made a name for himself Read more...

In 2003, Chappelle debuted his own weekly sketch comedy show on Comedy Central called Chappelle's Show. The show parodied many aspects of American culture including racial stereotypes, politics and pop culture. Along with comedy skits, the show also featured musical performances by mostly hip-hop and soul artists. Chappelle's pointed social and political commentary quickly helped the show garner Read more...

Chappelle was the subject and producer of the Michel Gondry-directed documentary Dave Chappelle's Block Party which chronicles a Chappelle-hosted event in the Bedford-Stuyvesant neighborhood of Brooklyn on September 18, 2004. The highlight of the event was the reunion of popular '90s rap group The Fugees. Chappelle toured several cities in February and March 2006 to promote the film under the moniker Read more...