In this classic sketch from the premiere of Chappelle’s Show season two, representatives from various races take turns “drafting” celebrities onto their “teams” in the same way sports leagues pick new players. In addition to cameos from Mos Def (as the black rep) and the Wu Tang Clan (which officially becomes Asian), there are some serious upsets over the likes of such early 2000s superstars as Tiger Woods (who finally issued a response in 2011), Halle Berry, Lenny Kravitz, and Colin Powell. The “Racial Draft” sketch exemplifies what Chappelle did best, mixing goofy-ass costume gags with sharp-as-hell political satire.
 
You can stream all of Chappelle’s Show seasons two and three on this site—click this link to check it out!