Chappelle was known for crafting jokes parodying racial stereotypes and the absurdity of racism. “The Mad Real World” flipped the script on the popular MTV reality show Real World by putting “one white person around the craziest black people we could find.” And the “Niggar Family” skit, featuring a white family with the last name Niggar being praised for using stereotypes about black people, played with language and racist ideology. The sketches stood in stark contrast to SNL’s stale slapstick shenanigans and awkwardly clumsy skits. Chappelle's Show, which ran on Comedy Central until 2006, was nuanced, politically smart, and hella black. However, Chappelle abruptly ended the show during production on the third season after signing a $50 million contract for two more seasons. Citing stress and manipulation, Chappelle took a sabbatical in South Africa and then went home to his farm in Ohio.

Many black artists are leery of being deliberately thwarted by white folks, whether due to systemic manipulation or cultural appropriation. Several hip-hop artists, like Lauryn Hill, Frank Ocean, and even Jay Z, have criticized the corporate cultural machine that exploits music for capital. Legends like Nina Simone and James Baldwin fled the United States for France, weary of America’s specific brand of racism and bigotry. Black folks understand the emotional toll of microaggressions and the nuances of racism in each generation. We respected Chappelle’s departure, yet mourned the loss of one of the greatest sketch comedy shows ever. This week, Chappelle returned to television with the much-anticipated debut of two of three Netflix stand-up comedy specials, The Age of Spin: Live at The Hollywood Palladium and Deep in the Heart of Texas: Live at Austin City Limits.