Charlie Murphy first showed the infamous Rick James sketch to his brother Eddie Murphy before audience tapings. Eddie enjoyed the sketch so much that the two watched it again.
The original opening theme was supposed to have lyrics, but the "band" couldn't synch the lyrics to the music. Dave told them to just keep saying "Chappelle's Show" over and over.
Somewhere in every episode of the second season the same man can be seen intensely dancing "The Robot." He is Karl Lake, set dresser for the show. In the first season he was asked to be in a crowd scene and do something funny. Chappelle liked the dance Lake was doing and made it a fixture of the second season.
Dave Chappelle left the show abruptly during filming of the third season. He later stated in interviews that he never intended to make a third season but he felt pressured by Comedy Central and his co-workers to continue. Comedy Central pulled the show from its 2005 schedule and decided to shelve the completed sketches in hopes that Chappelle would return to finish the season. Chappelle stated in interviews that if Comedy Central aired the episodes he would definitely not return to the show. After negotiations with Chappelle stalled, Comedy Central decided to repackage some of the completed sketches and air them in 2006. Charlie Murphy and Donnell Rawlings took over the hosting duties.
Unaired sketches shot for the aborted third season include: A parody of Michael Jackson's videos "Thriller" and "Beat It" referencing his child molestation trial. A parody of Super Size Me (2004) called "Maximize Me." A sequel to Daddy Day Care (2003) starring Charlie Murphy. Dave using the speech patterns of politicians to receive special treatment at a coffee shop and a strip club. A parody of the Virgin Mobile commercials featuring two singers on the street. A "Hip-Hop Newsbreak" portraying the lyrics of Nas's "If I Ruled the World." Dave imagining what would happen if he sold a ringtone and spoke at the Republican National Convention. A "Hip-Hop Newsbreak" stating lyrics of Dr. Dre's "Still D.R.E." Dave harassing his ex-girlfriend's husband at his job at a donut shop. A "Hip-Hop Newsbreak" stating lyrics of Das EFX's "They Want EFX."