The various roles that Dave plays throughout his show. Listed are a few of the important ones, and which episode(s) they appear in.

In what's now likely the most famous episode of Chappelle's Show ever, Dave plays rock superstar Rick James. The skit features cameos from the real Rick James, as Charlie Murphy recounts one of his True Hollywood Stories. This episode also spawned the now infamous catchphrase, "I'm Rick James bitch!" that became a phenomenon.

A bumbling crackhead, Tyrone has made a number of appearances throughout the series. The first time was him showing up at a "Drug Awareness Day" at a school to promote..crack. Following that mishap, he appeared in episode #108 as his family and friends tried to intervene in his drug habits. He also appeared in the Wayne Brady episode (#212) in an opening skit where he was a contestant on Fear Factor.

Only appeared in one episode, but Samuel L. Jackson was busy talking loudly and trying to sell his beer. IT'LL GET YA DRUNK!

Silky Johnson showed up in episode #109 to take part in the Playa Hata's Ball, an international insult event. Showed up again in the "Never Made It" episode (#211) where him and his Playa Hata Crew travel back in time and shoot a slave owner.

Dave plays The Artist in this classic Charlie Murphy True Hollywood Story. Follows their exploits after they meet at a club and decide to play some basketball at Prince's crib.

Second only to the Rick James episode in it's catching on with the mainstream, Dave plays CRUNK IDOL Lil' Jon in a barrage of WHAT?, YEAAAAH!, and OOOOOKAY!. This skit is the reason grandmother's know who Lil Jon is, and is just as tired as Rick James. Knock it off already!

A black version of Gallagher, that's actually funny!

This Harlem resident shot to fame as the world's richest man (beating Bill Gates!) thanks to a hot hand in dice in episode #104. He reappears in episode #205 as a cocaine trafficking white collar criminal.