Dave Chappelle will be awarded the Mark Twain Prize for comedy in 2019. That means this most American of comedians will get that most American of entertainment prizes. It’s a match made in heaven — a heaven that got dragged through hell first.
It’s no secret that America has always had a problem talking about race. And it’s often been comedy where we’ve found the truth we couldn’t find elsewhere. There have always been comedians pushing the envelope on race, asking people to see what was clearly before their eyes. From Dick Gregory to Freddie Prinze to Richard Pryor to Paul Mooney to Wanda Sykes, there has been no shortage of comedians bringing the painful and funny truth to our doorsteps.
But none of those talents was able to deliver such incendiary content directly into America’s living rooms the way Chappelle was, with the utterly singular Comedy Central Chappelle’s Show. Wasn’t ever anything like it before — and there hasn’t been since. (Although Jerrod Carmichael‘s less outrageous show knocked boldly, thoughtfully on the door, for sure.) Here are some of the best clips and skits from Chappelle’s Show.
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