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- 2003–200622mTV-MA8.6 (606)TV EpisodeDirectorNeal BrennanRusty CundieffStarsDave ChappelleBill BurrJonathan CorbettDave debuts Samuel Jackson beer, shows us how much cooler life would be if everything were in slow motion and reveals the latest picks in "The Racial Draft".
- 2003–200619mTV-MA9.4 (1.1K)TV EpisodeDirectorNeal BrennanAndre AllenScott VincentStarsDave ChappelleRashida JonesCharlie MurphyDave introduces The Love Contract and the first of Charlie Murphy's True Hollywood Stories featuring Rick James. Musical guest Ludacris.
- 2003–200621mTV-MA8.8 (625)TV EpisodeDirectorNeal BrennanScott VincentStarsDave ChappelleJonathan WalkerBill BurrCharlie Murphy reveals another True Hollywood Story featuring Prince, and Paul Mooney answers life's biggest questions as "Negrodamus." Cee-Lo performs "Call Me".
- 2003–200622mTV-MA7.9 (487)TV EpisodeDirectorRusty CundieffStarsDave ChappelleGeneva CarrRon JeremyDave considers what life is like for rap sensation Lil' Jon and imagines how sleazy the Internet would look if it were a place. Anthony Hamilton performs "Comin' From Where I'm From".
- 2003–200622mTV-MA8.1 (477)TV EpisodeDirectorRusty CundieffAndre AllenStarsDave ChappelleLinda DohertyTrish MinogueDave hosts his new game show "I Know Black People," with another installment of "When Keeping it Real Goes Wrong"; musical performance by Erykah Badu.
- 2003–200622mTV-MA8.0 (482)TV EpisodeDirectorRusty CundieffStarsDave ChappelleRick CromJim BreuerDave broadcasts the World Series of Dice and spends another moment in the life of Lil' John; musical performance by Common & Kanye West.
- 2003–200622mTV-MA8.0 (443)TV EpisodeDirectorNeal BrennanStarsDave ChappelleKadene KerrYoshio MitaDave imagines life as Oprah's baby's daddy and shares his experience as a jury member on the OJ Simpson trial; musical performance by Wyclef Jean.
- 2003–200622mTV-MA8.0 (658)TV EpisodeDirectorAndre AllenRusty CundieffScott VincentStarsDave ChappelleRandy PearlsteinMelle PowersDave's sketches include a parody of 'The Real World, with an all-black cast and one white man.