Dave shows a girl who curses her breasts the error of her ways and shares hilarious outtakes from Roots; musical guest Talib Kweli.

Dave shows us what happens when couples try "Trading Spouses" and introduces a family-friendly brand of pot; musical guest Blackstar.

Dave Chappelle plays America's most vicious blind white supremacist and unveils racy "bootie" videos starring Nat King Cole.

Dave uncovers racism among Hollywood's animal stars, and Tyrone Biggums returns when his friends hold an intervention; musical guest Slum Village.

Dave Chappelle runs for office and shows us how much cooler life would be if everything were in slow motion.

Dave explores the myth that white people can't dance and charts his own emotional growth; musical guest John Mayer.

Dave hosts "Who Knows Black People" and an installment of "When Keeping It Real Goes Wrong;" musical guest Erykah Badu.

Dave sees people's inner thoughts and freaks out when a little kid beats him at video games; musical guest De La Soul.

Dave introduces The Love Contract and True Hollywood Stories featuring Rick James; musical guest Ludacris.

Dave reflects on "Great Moments in Hookup History" and dares viewers to "Ask a Black Dude"; musical guest Fat Joe.

Dave looks at TV gambling sensation the World Series of Dice; Eddie Griffin guest stars with musical guests Common & Kanye West.

Crackhead Tyrone Biggums returns as a guest on Fear Factor; special guests Joe Rogan, Nick Cannon, and Wayne Brady.

Dave takes a realistic look at "Pretty Woman" and "The Matrix" and introduces the Wu-Tang Clan's new financial consulting firm; musical guest...

Dave presents the History Channel's coverage of great inner city gang wars from the 1980's; musical guest Gza.

Dave takes a realistic look at "Pretty Woman" and "The Matrix" and introduces the Wu-Tang Clan's new financial consulting firm; musical guest...

Dave presents the History Channel's coverage of great inner city gang wars from the 1980's; musical guest Gza.

Paul Mooney answers life's biggest questions as "Negrodamus;" Prince hits the basketball court; musical guest Cee-Lo.

Dave Chappelle runs for office and shows us how much cooler life would be if everything were in slow motion.

Dave imagines a black, watermelon-smashing Gallagher and Paul Mooney guest stars as "Negrodamus;" musical guest DMX.