The second episode of the "lost" third season of , titled "Black Howard Dean & Stereotype Pixies," is widely regarded as the most consequential installment in the series' history. Aired on Comedy Central on July 16, 2006, it features the material that directly preceded Dave Chappelle's infamous departure from the show and his spiritual retreat to South Africa. The Sketches
: The experience led Chappelle to question whether his work was reinforcing the very racism he aimed to expose. Fearing he had crossed a line from critique to complicity, he walked off the set during the pixie sketch and did not return to complete the season. [S3E2] Black Howard Dean & Stereotype Pixies
: Dressed in blackface, the pixie attempts to convince Chappelle (playing himself) to order fried chicken on a flight. The second episode of the "lost" third season
: The sketch also features an Asian pixie, a Latino pixie enticing a man to "pimp" his car with leopard print seats, and a "bland" white pixie. Historical Significance & "The Laugh" Fearing he had crossed a line from critique
: While filming the Black Pixie segment, Chappelle reportedly heard a white crew member (or audience member) laughing in a way that felt uncomfortable. He felt the laughter was coming from a place of enjoying the stereotypes themselves rather than the irony or satire intended.
This episode is primarily remembered for the "Stereotype Pixies" sketch, which became the catalyst for Chappelle leaving his $50 million contract.