The third season hit a big speed bump in November 2004. He was taping a sketch about magic pixies that embody stereotypes about the races. The black pixie—played by Chappelle—wears blackface and tries to convince blacks to act in stereotypical ways. Chappelle thought the sketch was funny, the kind of thing his friends would laugh at. But at the taping, one spectator, a white man, laughed particularly loud and long. His laughter struck Chappelle as wrong, and he wondered if the new season of his show had gone from sending up stereotypes to merely reinforcing them. “When he laughed, it made me uncomfortable,” says Chappelle. “As a matter of fact, that was the last thing I shot before I told myself I gotta take fucking time out after this. Because my head almost exploded.”
When Dave realized what Whites were really laughing at on his shows.