Chappelle’s Show
Dave Chappelle left no stereotype unmocked in brilliant sketches like “The Racial Draft,” in which various races tried to claim people of mixed ethnicity. Every episode of Chappelle’s Show had something to offend you, from Rick James’ catchphrase to homeless crack addict Tyrone Biggums.
Even Chappelle wasn’t always sure people were laughing at the right things — he left while shooting the show’s third season after an incident in which a white spectator laughed at a sketch about stereotypes in the wrong way, and made Chappelle question whether his show was subverting stereotypes, or adding to them.
“When he laughed, it made me uncomfortable,” Chappelle told Time. “As a matter of fact, that was the last thing I shot before I told myself I gotta take f—ing time out after this. Because my head almost exploded.”
Chappelle, of course, is one of the most successful standup comedians of all time, and continues to offend people, even in the Netflix special he just released. He continues to not care if you’re offended.
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