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Retrospective: The Top 10 Chappelle's Show Skits

By @TrueGodImmortal

Dave Chappelle is a legendary comedian. Hands down. His iconic Chappelle's Show remains in TV history. Today, we wanted to look at the classic show and select the top 10 skits from it. This was not easy to structure and list, as it is more so my personal opinion versus the general consensus, and some classic skits just missed the mark unfortunately. We will always appreciate the Wu-Tang Financial, Reparations, WacArnolds, Fisticuffs, 2Pac, Lil Jon skits however, but those just missed the list. Read and let us know which Chappelle's Show skits are your favorite in the comments below.

10. Making The Band/R. Kelly's Piss On You(Tie)
Season 2, Episode 10/Season 1, Episode 10

-I know, I know. Starting off the list with a tie. There was no way that I could make a decision between these two. Both are iconic and hilarious. The "Making The Band" skit was truly entertaining as Dave took on the role of Diddy, with actual members from the show. He even plays Dylan, the 5th member of the group which provided us with the classic "Dylan, Dylan, Dylan, Dylan, and Dylan, cause I spit hot fire" quote. Dave even plays Fonzworth Bentley as the skit ends, making this THAT much better.

-Now, with the R. Kelly video, we have to include the original, as well as the remix. This has to be included for the sheer absurdity, hilarity, and genius that it displayed, as Dave creates outrageous lyrics backed by a ridiculous music video. The lyrics "only thing that makes my life complete/ is when I turn your face into a toilet seat/", along with the sight of a bucket labeled "R. Kelly's Doo-Doo Butter" makes this skit(along with the remix skit) a top 10 Chappelle's Show skit.

9. Clayton Bigsby
Season 1, Episode 1

-Some may view this as the best skit on the show, and while I agree that it is a classic, I couldn't place too high. However, this skit completely set the tone for the future of Chappelle's Show, knocking it out the park on just the first episode as Dave plays Clayton Bigsby, a blind black white supremacist who doesn't realize he's actually black. The moment he finds out he is really black, everything changes, including him divorcing his wife for marrying a black man(himself... Haha). True classic.

8. Trading Spouses
Season 1, Episode 12

-Leonard Washington. The man, the myth, the legend. This is where it all started. On an episode of Trading Spouses, Leonard and a white man named Todd(both of course played by Dave) switch places for a while, to see how they would adjust with their new family. Todd has a hard time getting his "new wife and son" to adjust to eating parsnips("what the fuck is a parsnip"), while Leonard drops quote after quote while not adjusting well to the new white family. Talk of lightsabers, scorching the earth, and G-G-G-G-Unit(or rather, "G-G-G-Goodbye") ensues along with massive hilarity.

7. Playa Haters Ball
Season 1, Episode 9

-This might be my personal favorite skit of all time, as it gets quoted on the regular. Ice-T and Patrice O'Neal guest star in this skit, which tells the story of the Playa Haters Ball, where they honor the most diabolical haters this side of the Mississippi. Silky Johnson, who is played by Dave, provides an amazing amount of laughs here, giving quote after quote. This is a true gem and one that I feel is supremely underrated. It is one of the best, hands down.

6. Black Bush
Season 2, Episode 13

-I slept on this skit admittedly. I hadn't watched it enough to grasp the full genius of it, and while I always thought it was great, it became a classic to me. Mos Def was amazing here, providing an extra spark to this skit, while Dave played this whole thing perfectly. Jamie Foxx even made an appearance as the black Tony Blair, which was also hilarious. So many quotes, laughs, and once again, genius.

5. The Racial Draft
Season 2, Episode 1

-This is yet another iconic skit that still gets talked about today, hell I see racial drafts being used as jokes all the time to this very day. Dave created a talking point with this skit and the Tiger Woods speech is absolutely brilliant. Mos Def once again shines here, and after all the selections are made, you are left wondering and thinking, which was a big part of the show's success. Thought-provoking, yet genius comedy. Nobody did it better than Dave.

4. Mad Real World
Season 1, Episode 6

-This skit was my favorite for a while. I used to quote this regularly. Who could forget the quotes from Tron? "Niggas is wilding", "Katie got some big ass tittays", "and a Banana Cognac, BITCH", etc... The quotes here were endless. Charlie Murphy was hilarious as well, especially in his interactions with the only white guy in the house. The premise was simple: put a white guy in the house with some of the craziest black people possible, in a reverse version of The Real World. This skit is one I could watch over and over. Truly one of the best.

3. Wayne Brady 
Season 2, Episode 12

-You knew this was going to be on here. There was no way possible that you can have a Chappelle's Show list and not have this skit/episode on it. Chappelle begins the episode by quitting the show and they replace him with Wayne Brady as the host. From there, Dave attempts to get his show back, before showing a night out with Wayne that resulted in pimping, gunfire, a cop getting his neck snapped(as Wayne was singing a song), and Dave losing his sandwich.... All done by Wayne. Absolutely brilliant work by both Wayne and Dave, giving us the legnedary quote, "Is Wayne Brady going to have to choke a bitch?".

2. Charlie Murphy's True Hollywood Stories: Prince
Season 2, Episode 5

-I won't lie... I debated between the first two. Both are classics. Both are Charlie Murphy's True Hollywood Story skits. Based off the show's growth and what stood out as iconic the most, I had to put this one at number 2. Personally, it is likely better than the Rick James skit, as it doesn't run as long, and features more laughs in a shorter time. Dave plays Prince, as Charlie narrates a story from when he and his brother Eddie hung out with Prince once and played basketball.... Then lost and got served pancakes. The ridiculousness of the whole skit is what carries it beyond the average and this is without a doubt one of the best. Period.

1. Charlie Murphy's True Hollywood Stories: Rick James
Season 2, Episode 4

-Was there really any other choice? Objectively speaking, there was no way this couldn't be number 1. Even as I pondered putting the Prince one above this, I realized that it was impossible. This is the most iconic episode from Chappelle's Show hands down. Even the deleted scenes and bloopers are hilarious("interracial dating... Who ya gonna run to... THAT'S RIGHT"). Each and every time I watch this episode, I find something new to laugh at, along with the iconic jokes. This skit/episode helped to push Rick James back into pop culture, immortalizing him for a whole new generation that might not have been around for his music or at least weren't as familar with him. A classic episode from top to bottom, with both Charlie and Dave providing nothing but genius comedy, and even Rick gets in on the fun, by appearing and helping to describe the entire narrative. The 80s were full of big music, women, and lots and lots of coke. This episode cements that fact. Cocaine is a hell of a drug!

With our top 10 list finished, what do you think? Have a list that features other skits? You agree mostly with this list? Let us know in the comments.


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