Photo sources: Comedy Central

Every Single ‘Chappelle’s Show’ Sketch (Except One), Ranked

Three seasons. Twenty-eight episodes. Untold cultural impact. It’s all here.

Keith Murphy
Published in
50 min readSep 8, 2020

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By the time comedian Dave Chappelle was a 14-year-old prodigy turning heads in Washington, D.C.’s stand-up clubs, he was already building the foundation for what would become the most groundbreaking sketch show of the 21st century. The skinny minister’s kid was not yet ready to tackle adult-themed humor in 1987, but he wasn’t afraid to explore the dangerous minefield of race that would fuel much of the success of his genre-shifting series, Chappelle’s Show.

“Jesse Jackson was running for president, so I used to do jokes about that,” he told NPR’s Fresh Air back in 2005, alluding to the Black civil rights icon’s second run for the White House. “I’d talk about stuff I saw on TV, like Alf. But they all had race in them, one way or another. Alf, my whole thing, was like, an alien comes 3 billion miles from space and gets a home with a White family… which all sounds corny now, but remember, I was 14, so it was like, wow.”

When Chappelle’s Show premiered on Comedy Central on January 22, 2003, it didn’t just disrupt the predominantly…

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Keith Murphy
Writer for

Mr. Murphy’s work has appeared in such publications and online sites as VIBE, The New York Post, Billboard, ESPN’s The Undefeated, OZY, and Esquire.