The Top Ten Chappelle Skits Of All Time In Honor Of ‘Chappelle’s Show’s’ 13th Anniversary


If you’re a TV guy like myself, you probably found yourself having “The Best TV Shows of All Time” debate every now and again and really there’s no right or wrong answer. You’ve got your dramas, your comedies, late night specials, all time classics, documentaries, etc. There are literally thousands upon thousands of options you can slide in that make just about every list near impossible to nail down, but one show that’s mentioned along with the all time greats time and time again is ‘Chappelle’s Show.’ Is it the best show of all time? Probably not. Is it the funniest show of all time? Maybe, but I think one thing just about everyone can agree on is that ‘Chappelle’s Show’ is probably the single most influential TV show of our generation. To this day ‘Chappelle’s Show’ remains one of the most socially relevant, most quotable, and most widely loved programs to ever grace home television screens. Quotes like “I’m Rick James, bitch!” still play without making you sound like the try hard guy that still quotes Borat and skits like “The Racial Draft” have spawned memes and Twitter accounts that still generate a laugh just about every time. In honor of ‘Chappelle’s Show’s’ debut 13 years ago today (makes you feel old AS FUCK, no?), here are my top ten favorite skits in show history. Is this list air tight? Not a chance and when I go back and read this some time in the future I’ll probably think of five or ten more that could have made the cut, but these are my personal favorites from a show that sparked a revolution.

10. The World Series of Dice

The World Series of Dice often gets lost in talks of the greatest Chappelle skits. Likewise, Leonard Washington and Ashy Larry looking drier than Kunta Kinte’s ankles are probably the two most underrated characters in show history.

9. True Hollywood Stories – Rick James

Dave as Rick James is probably the most quotable character in show history. “I’M RICK JAMES BITCH!” Also I’ve never doubted for one second of my life that this story isn’t 100% true. Too outlandish to not be, right?

8. Black Bush

Can you believe the former head of the CIA and Bush’s right hand man got arrested on immigration charges in South Africa the other day? Must have been over there following up on some yellow cake. YELLOW CAKE!

7. Tupac Is Alive

I’m on record as saying Tupac is still very much alive and well (he’s in Cuba) which lends a lot of credibility towards said skit. Also this song should be recorded digitally for mass distribution. The doo doo bar is fire.

6. Wayne Brady Show

“Hoes, Dave. Dave, hoes.”

Putting the Wayne Brady bit in the top ten may seem like a bandwagon pick. Maybe it is, but I don’t think anyone has ever looked at Wayne the same after seeing him letting it ride sideways out the coupe and threatening to choke a bitch. He’s basically Malcolm X in my eyes now.

5. The Player Hater’s Ball

In addition to being in the running as the GOAT skit, Silky Johnson is in the running for the GOAT Chappelle character. “Why don’t you click your heels together three times and go back to Africa?” and the pubic hair coat bit are both first ballot hall of fame lines.

4. Reparations 2003

In a show known for pushing the limits on racial humor and stereotypes, this one is right up there at the top. If you don’t cackle at the Kool truck and Escalade lines though, you might have Aspergers.

3. Clayton Bigsby – The Black White Supremacist 

Clayton Bigsby missed the top spot by a hair, but God damn this skit is still one of the funnier things I’ve ever seen on TV. To think that this was the first skit Chappelle ever did is kind of incredible seeing as they came out of the gate firing on all cylinders and never really slowed down.

2. The Racial Draft

I’ll venture as far as to say the racial draft is the most iconic Chappelle skit and it’s not even close. Still as funny as it was 13 years ago, although this year’s racial draft would look A LOT different. I’m thinking something like this:

  1. Black Delegation selects Dwayne ‘The Rock’ Johnson, trades rights to Stacey Dash
  2. Jews select Drake
  3. Latinos select Marco Rubio
  4. The White Delegation selects Blake Griffin
  5. Manny Pacquiao (weak field for the Asians this year)


1. True Hollywood Stories – Prince

Honestly any one of these skits could have taken the top spot, but when I was searching for no. 1 I had to disregard social relevance, quotability and all that shit. Only thing I’m looking for is the skit that made me laugh harder than anything else and to this day, the Prince Skit may have been the hardest I’ve ever laughed at anything I’ve ever seen on TV the first time I saw it. Not sure that’s gonna get topped either. The Prince Skit should be the measuring stick with which all things dubbed “laugh out loud funny” should be judged.


About Q-Ball

Owner, operator AKA The Commish. Q-Ball is that asshole at the office who refuses to brew a fresh pot of coffee. Not because he doesn't want to, he's just too embarrassed to admit that he doesn't know how.
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