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The Chappelle Show At 20: 10 Favorite Skits

Just like that my friends it is the 20th anniversary of The Chappelle Show. Debuting January 22, 2003 and running for only two full seasons and a mashed up third for a total of 28 episodes. The show had pop culture in a full press choke hold during it's run. 20 year's later it still has a hold on much of society. Especially those of us who were teenagers/young adults during the show's initial run.

I always found Dave Chappelle as a funny guy, but it wasn't until his 2000 HBO special Killin' Them Softly that I realized what a genius he is. The genius trait carried over into The Chappelle Show leaving us with several memorable skits and characters. To Celebrate the man and the show, here are ten of the funniest skits during the show's run.

10. Kneehigh Park

This skit aired on season 2 episode 10 of the show. It's a parody of Sesame Street, which Dave riffed on previously in his stand up special. Kneehigh Park is a rougher version of Sesame Street where the kids are introduced to life lessons such as the dangers of drugs, std's like herpes and crabs, and the cynical view of life and society the older you get (a very important life lesson). Stinky The Grump (Hilariously voiced Charlie Murphy) help's drive that point home when his famous "Fuck It" jingle. Kneehigh Park is not one I hear people reference much, but each segment is very funny and the overall skit is highly underrated.

9. Tyrone Biggums

The World was introduced to Tyrone Biggums in the second episode of the first season. A functioning crackhead impervious to pain and willing to do whatever for his next hit. He would be a recurring character throughout the shows run. In his debut skit he talk's to a classroom about the dangers of smoking crack to be a dealer.

8. Making The Band

In the early 2000's MTV's Making The Band starring Diddy (Then known as P. Diddy) was a sensation. It was such an sensation the rap group he put together Da' Band were actually considered hot. This sketch was genius, featuring actual four members of the band and Chappelle playing both P. Diddy and Dylan.

The sketch riffed on Diddy's consistent threats to shut the studio down during the show, and his famous walk to Brooklyn for some Juniors cheesecake scene. Of course the sketch is most famous for the top 5 rappers of all time line...Dylan, Dylan, Dylan, Dylan, and Dylan.

7. Piss On You

Aired during season 1 episode 10, Dave Chappelle sampled R. Kelly's "Feeling On Your Booty" single from a couple years earlier and used the sex tape scandal featuring R. Kelly pissing on women, to create comedy gold. If you don't find the two song's "Piss On You" and the "Piss On You" remix (which samples ignition remix) please please check your pulse. If some reason you have never seen either sketches here's Piss On You and the remix

6. Wayne Brady Show

Season 2 episode 12 in a bit of meta foreshadowing centered around Dave Chappelle unhappy with negotiations for the next season of the show, walking off. In his absence Wayne Brady was bought on to host the show. Along with a Fear Factor segment, the funniest skit was a Training Day inspired sketch featuring Wayne Brady and Dave Chappelle on the town. Dave as well as the audience were SHOOKED to see an aggressive, vengeful, murderous Wayne Brady. His most famous line "Is Wayne Brady going to have to choke a bitch?" is still quoted to this day.

5. Racial Draft

Oh boy this one is Gold!! and I don't think anyone else could have pulled it off. The Racial draft a spoof on the hoopla and hype surrounding the NFL draft. It features cameos by Mos Def, Angie Martinez and Rza. The purpose of the Racial Draft was to draft people into a race based on their perceived ethnicity. Describing it won't do it any justice just watch the skit.

4. Lil' Jon

In the early 2000's much like Making The Band was a sensation, Lil' Jon and the crunk era of Hip Hop and R&B was an juggernaut. Everytime you turned on the radio or BET and MTV (back when they played music videos) a Lil' Jon produced song was guaranteed to be in the rotation, in fact most times that's all that was in the rotation.

It was only right Chappelle made him a target with A Day In The Life of Lil' Jon. It includes moments at the airport and the doc's office. The skit is even funnier when Chappelle as Lil' Jon has a phone conversation with the actual Lil' Jon. The skit is filled with a lot of "yeahhh's" and "Whattt".

3. Player Hater's Ball

There's Players and the Player's Ball and there's Hater's and The Player Hater's Ball. In The Chappelle show world, The Player Hater's Ball is a convention of verbal abusers or in better terms who can roast other's the harshest. Featuring cameos by Ice-T and Patrice O'Neal, the fact the haters dress up like pimps is even more hilarious. Check out the skit your stomach will hurt from laughing so hard.

2. Clayton Bigsby

Audiences were introduced to Clayton Bigsby on the very first episode of The Chappelle show, and that skit should have been a clue that we were in a ride of something different, thought provoking and hilarious. Clayton Bigsby is a blind white supremacist who just so happens to be Black. He is top 3 fictional Uncle Tom's behind Uncle Ruckus and Stephen (D'Jango Unchained). In real life there are a lot of Black people like this.

The skit is so hilarious because it's a Deadline style segment featuring his life story, his hatred of Black People, and how he is so revered in the white Supremacist community although no one has ever seen his face. Which leads to a hilarious end to the sketch.

1. Charlie Murphy True Hollywood Story

Come on could anything else have been the best skit of the Chappelle show series? The skits featured Charlie Murphy (who was an excellent storyteller) recalling wild time's of the 80's he came across some celebrities hanging with his brother Eddie. The first of course is the story of the time Prince beat him and his friends in a game of pick-up basketball, but it's how they get to that point that's a riot.

The second more popular story is a night out on the town with Rick James (who was very good friends with Eddie). Rick was a wild boy in his day and this story further highlights it. The sketch further accentuates how wild Rick was, by having Rick James himself provide some commentary on the going-on's in the skit. The sketch is famous for two lines still uttered today, "Fuck yo' couch" and of course "I'm Rick James Bitch".

The Chappelle Show was something special and it was hard narrowing down this list to only 10 skits. I missed some good ones (Samuel L. Jackson Beer), but that's the beauty of the show it was gold all the time. Researching for this blog, I was laughing my ass off at these skits like it was my first time watching them. Which proves how timeless the show was and why it's still loved today.

Cheers to 20 Years Chappelle Show!

About The Author

B is a 1500 original. He loves movies, pro wrestling, and traveling. His dream is to one day be able to travel around the world at his leisure. He also is a pro wrestling blogger for his brand at He also has a geek branded blog at Follow him on IG @astorybyb where you may find some of the most random questions and polls known to man.

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