4. 'Chappelle's Show' (2003-2006)
"What is life is nobody's crossing the line?" Dave Chappelle asked on Inside the Actor's Studio. "You just want to try to be on the right side of history…the truth is permanent, and everything else will fall by the wayside." Both populist and pointed, Chappelle's Show tackled race relations with a colloquial sort of lucidity that refused to leave anyone out of the conversation. Celebrity caricatures ("I'm Rick James, bitch") became immediately quotable, but Chappelle's Show really shone in scathing scenes like that of Clayton Bigsby — the blind white supremacist who doubles down on his bigotry after learning he, in fact, is black. Though the show's third season was cut short when Chappelle abruptly fled to Africa, leaving the network and co-creator Neal Brennan in the lurch, it cemented a legacy not likely to fade anytime soon. In the land of awkward white guys doing silly walks, it's hard to imagine a cooler sketch show.