The 6 best ‘Chappelle’s Show’ sketches ever

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Editor’s note: The following article is an op-ed, and the views expressed are the author’s own. Read more opinions on theGrio.

“Chappelle’s Show” remains one of the most iconic sketch comedy shows of all time. I still hear people quoting the show. Dave and his team, including co-creator Neal Brennan, knew how to combine pro-Black political ideas and comedy in a way that no one else ever has. Choosing the show’s best sketches is a challenge because there are so many great ones. But true fans of the show have a list. Here are mine.

6. Reparations 2003 

To see Black people running around with reparations money is a joy in and of itself. The happiness they exude as they fan themselves with money is genius. This is a great example of how “Chappelle’s Show” mixed pro-Black politics and comedy.

5. The Racial Draft

We all know there are some Black people we’d like to nudge out of the race and a few white people who we wouldn’t mind “becoming” Black, symbolically or honorarily or whatever. This sketch brings that notion to life and it skewers the complexity of modern race. Nowadays, lots of people are bi-racial or multiracial or multicultural, and asking them to choose one race or the other is complicated and nearly impossible. This sketch demands we be binary about race and it comes off hysterical. 

4. The Niggar Family

I love “Chappelle’s Show” for finding a way to say the n-word on TV over and over. I love them for turning racial stereotypes upside down and poking fun at their ridiculousness. But what “Chappelle’s Show” does incredibly well is combining comedy and political ideas, and in this sketch, we have Chappelle as an everyday milkman who’s subverting the system by laughing at the Niggars, and he’s having a blast doing it, but he’s laughing to keep from crying. At the very end, Chappelle’s character says, “Oh this racism is killing me,” and that one line elevates the sketch to a portrait about the pain of living inside a white supremacist system. When I interviewed “Chappelle’s Show” co-creator Neal Brennan for my book, “Who’s Afraid of Post-Blackness?” he told me that that last incredible line — “Oh this racism is killing me” — was improvised. That made me respect Chappelle’s comedic gangster even more. 

3. The Mad Real World

This is a hilarious take on a white boy’s failed attempt to live in a reality show house with a group of Black people. “The Real World” was a massive part of pop culture back when “Chappelle’s Show” was on, and to see an all-out takedown of that whole show is hysterical. Generally, comedy that asserts “Black people are like this and white people are like this” leaves me cold, but Chappelle does that in this sketch in a powerful way.

2. The Wayne Brady Show

This one gets deep. Brady is sometimes seen as a much more, can we say, Oreo-ish performer. In one epic “Chappelle’s Show” sketch, Paul Mooney says “White people love Wayne Brady because he makes Bryant Gumble look like Malcolm X.” Translation for the youngs: Brady is non-threatening to whites. Anyway, Chappelle ran into Brady, who said the sketch had hurt his feelings, and they got to talking and the idea for this epic moment soon followed. Sure, Brady seems Oreo-ish, but you know what they say in Jack and Jill: Never judge a Black man by the cable knit of his sweater. (No they don’t actually say that.) What if, away from the stage, Brady was actually a tough guy? A wild pimp? A shooter??? It blows me away that this sketch is really about the notion that you can never really know who a Black person is. You can’t judge. Just because they might seem Oreo-ish does not mean they are. 

1. Frontline: Clayton Bigsby, the Black white supremacist

This powerful sketch destroys me every time. It’s about Black people betraying their race, the pathetic nature of white supremacists and the desire to be another race. It’s genius. Brennan told me Comedy Central did not want this episode to be part of “Chappelle’s Show’s” first episode. They were adamant. Chappelle said either I get this or I walk. He was right. This sketch blew minds and set the whole tone for the show: They were going to attack — viciously, intelligently but comedically — anything. They were going to be smart, they were going to be political and they were going to kill. And they did. “Chappelle’s Show” remains the best comedy sketch show ever. Yes ahead of “SNL,” “In Living Color,” “Key & Peele” — all of that. No one touches the genius of two and a quarter seasons of “Chappelle’s Show.”

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Touré is a host and Creative Director at theGrio. He is the host of the docuseries podcast “Being Black: The ’80s.” He is also the host of the podcast “Toure Show” and the podcast docuseries “Who Was Prince?” He is the author of eight books including the Prince biography Nothing Compares 2 U and the ebook The Ivy League Counterfeiter.

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