The 15 Best ‘Chappelle Show’ Skits, Ranked

From Rick James to Wayne Brady, here are our favorite ‘Chappelle Show’ sketches.

Dave Chappelle
Comedy Central

Image via Comedy Central

Dave Chappelle

Ranking the best sketches in Dave Chappelle’s seminal Chappelle’s Show is no easy feat. The show has transcended pop culture—becoming a lightning rod for topics that no one would speak about, and for social issues that are still a problem to this day. It’s inconceivable that the show would have even flourished this much in a Bush Presidency, with its dense writing about race, identity, and politics—but a truthful brand of comedy was the cure all that we needed in the post-9/11 world.

Digging through hours of the show wasn’t something that I didn’t look forward to, but I did figure that I’d give a disclaimer to why things are ranked how they are. Sure, the punchlines and memes were funny, but Chappelle’s Show was much more than that—it made you think. This ranking takes the most important cultural moments, over the ones you repeated at your class/watercooler/Myspace account back in 2003. Sketches that stood the test of time, and probably wouldn’t make Chappelle himself cringe if you recited them in public (Looking at you, people who still shout “I’m Rick James, bitch!” at him). So here it is, the ranking of the most important Chappelle’s Show sketches. 

15. "Charlie Murphy’s True Hollywood Stories: Rick James"

Season 2, Episode 4

Air Date: February 11, 2004

Okay, before you write angry, hate-filled epithets in the comments—the ranking of one of the most infamous sketches in TV history this low doesn’t mean it is bad. However, it is a little bit overrated in the larger scheme of the Chappelle’s Show canon. Featuring Charlie Wilson narrating his sometimes rocky friendship with Rick James, the first edition of “C True Hollywood Stories” features Chappelle playing Rick James at his peak (with an assist from the real Rick himself in equally hilarious confessional footage), platform shoes, dreadlocks and all. The main beat of the story still holds up today, but unlike other Chappelle’s Show sketches, it hasn’t held up much past the actual punchlines (here’s looking at you, Lil Jon sketch). It is, however, still one of the finest examples of comedy transcending pop culture and honoring one of the greatest musicians of all time.

 

14. "Pop Copy"

Season 1, Episode 1

Air Date: January 22, 2003

The reason we loved Chappelle’s Show was because of its endearing approach to the everyman—and “Pop Copy” showed that sensibility in spades. Taking place in a dysfunctional Print/Copy shop, "Pop Copy" reunited Dave with his Half Baked co-star Guillermo Diaz in this informative commercial about how Pop Copy operates and treats their customers with “care.”

13. "Knee High Park"

Season 2, Episode 10

Air Date: March 24, 2004

Mixing puppets, children, drugs, and STDs may seem like a recipe for disaster, but Chappelle’s Show’s “Knee High Park” sketch thinks outside the box and makes it work. The Sesame Street inspired satire was Chappelle’s way of cutting the bullshit and teaching kids about the real issues in the world, by both offending and probably pissing off people in the process. Snoop Dogg makes a great cameo here as well, lending his vocals to a song about, what else, sex addiction and disease. 

12. "Black George Bush"

Season 2, Episode 13

Air Date: April 14, 2004

The Black George Bush sketch resonates as much if not more now than it did at the time it aired on Chappelle’s Show. Starting with Dave asking if things would be different if George Bush was a black man, “Black Bush” is a sobering look at how things would be if a black man was running the country. He’d be real, blunt, and most of all—he’d be like someone that we all knew. Wait, that sounds familiar. 

11. R. Kelly “Piss On You”

Season 1, Episode 10

Air Date: March 26, 2003

Even though it had a lot of social/political commentary, Chappelle’s Show wasn’t above going low-brow, and Dave’s spoof on R.Kelly’s salacious legal battle was quite the topic to take aim at (no pun intended, of course). Becoming just as famous as the song it was based on (“Ignition Pt. 2”), “Piss On You” proved that Chappelle had a pretty bad ass R. Kelly impression, and he could carry a tune too. Drip, drip drip!

10. "Fisticuffs"

Season 1, Episode 11

Air Date: April 2, 2003

Rap music was a huge inspiration on Chappelle’s Show, and he had more than his fair share of skits that poked fun at the familiar tropes at the time. The introduction of deaf rapper Fisticuffs was perhaps the best example of this, a joyously funny lampooning of the SMACK DVD culture that permeated in the mid 2000’s. Taking viewers through a day in the studio with Fisticuffs, you get a peek inside his interesting song making process. Yes, you’ll probably be going to hell for laughing at this, but it’s a small price to pay.

9. "Racial Draft"

vimeo.com

Season 2, Episode 1

Air Date: January 21, 2004

An ode to the rigorous draft process of professional sports, Chappelle’s Show’s racial draft was a sketch created to answer life’s burning questions like: “What if black people traded OJ to white people?” Jokes aside, this sketch was not only funny, but served as a deep analysis on the role of racial identity—which was a major theme in the three seasons of the show. On the outset, viewers will laugh at the absurdity of trading Tiger Woods to the Asians, but on a deeper level—it posits the notion that all races are somewhat jaded on the definition of what they are, becoming much more than the sum of its punchline.

8. "Charlie Murphy’s True Hollywood Stories: Prince"

Season 2, Episode 5

Air Date: February 18, 2004

Game. Blouses. In honor of the Purple one himself, and the fact that the story is so absurd, Charlie Murphy’s second True Hollywood Story has to place high on the list. Depicting an unforgettable night on the town, and an even more bewildering game of basketball afterward, Charlie tells the story of how Prince got the best of him. Even without the accompaniment of the man himself as a cameo in the episode, Chappelle’s impersonation of Prince is an all-timer. Even if it doesn’t reach the level of absurdity that the Rick James episode had, the punchlines here are more thought out and generally less annoying.

7. "Playa Hater's Ball"

Season 1, Episode 9

Air Date: March 19, 2003

The collection of characters from the Playa Hater’s Ball are some of the most popular recurring sketches on Chappelle’s Show. They’ve joked Diddy’s “dolphin teeth,” gone back in time to shoot slave owners, and in a testament to their legendary status—even appeared recently during Dave’s hosting gig on Saturday Night Live. The adventures Silky Johnson, Buc Nasty and the gang weren’t as deeply rooted in social issues as the other sketches on this list—but they were just plain funny.

6. "The Niggar Family"

Season 2, Episode 2

Air Date: January 28, 2004

Chappelle’s Show was all about uncomfortable, yet thoughtful humor—regardless of who was the target. So when it came to fan-favorite sketch “The Niggar Family,” it raised a huge question. Sure, you see how it’s spelt—but can you really SAY it? Much more than the punchlines littered throughout, “The Niggar Family” deals with inclusion in terms that everyone can relate to, but are afraid to talk about. Framed as a old-school 1960’s sitcom about a white family with an unfortunate nickname, Chappelle probably managed to get the “N” word (Niggar, not the other one) on-air more than any other television show since Roots. If you felt dirty saying it, that’s the point.

 

5. "Making the Band"

Season 2, Episode 10

Air Date: April 7, 2004

It’s no secret that Dave was a big fan of MTV shows, but no one could have prepared us for his lengthy sketch that parodied Making The Band. Featuring the cast of the show, minus Dylan (Dylan, Dylan, Dylan, and Dylan), it was an encapsulation of what made the drama-filled and messy show such a phenomenon upon its airing. Bonus points go to Dave’s impersonation of Diddy (who got a lot of shots in general on Chappelle’s Show). 

4. "The Wayne Brady Show"

Season 2, Episode 12

Air Date: April 7, 2004

If perception versus reality was a big motif in Chappelle’s Show, nothing exemplifies this than this sketch, where Chappelle goes on a deadly ride along with Wayne Brady—who he had declared “soft” in a previous episode. Giving viewers a classic punchline (“Is Wayne Brady going to have to choke a bitch?”) and an even funnier Training Day-esque satire, The “Wayne Brady” sketch is a rare moment where Dave took his foot off of the gas and let someone else become the MVP on the show.

3. “Frontline—Clayton Bigsby”

Season 1, Episode 1

Air Date: January 22, 2003

If you didn’t know that Chappelle’s Show was going to go THERE, then the introduction of Black-White Supremacist Clayton Biggsby in the first episode set the tone for the series as a whole. Framed as a nightly news expose, the sketch is a devilishly smart examination in the learned nature of racism. Clayton (played by Chappelle) is a blind black man who grew up as a right-wing, hate-filled white supremacist who doesn’t know he’s black. Within that hypocrisy, the sketch also follows the David Duke-like cult of Clayton who refuse to tell him the truth. It was and still is shocking and funny, and the punchline at the very end about Clayton’s wife will have you rolling on the floor. 

2. "Reparations"

Season 1, Episode 4

Air Date: February 12, 2003

Spawning a legendary soundbite, and at least ten quotable lines, the “Reparations” sketch from the first season of Chappelle’s Show was a funny, if a little controversial, look at what would happen of black people actually received reparations. In a clever way of playing on stereotypes and social perception, the show writes the sketch in a way that both blacks—and the businesses that profit off of them would react to such a monumental payback. The final punchline will hit you in the stomach, but it’ll also make you think, too. 

1. "Mad Real World"

Season 1, Episode 6

Air Date: Feb. 26, 2003

There can only be one truly perfect sketch in the two years that Chappelle’s Show reigned supreme—and it has to be “Mad Real World.” More of an amalgamation of the idea of cultural tolerance within pop culture than a true teardown, Dave posits the idea that MTV’s flagship reality TV show The Real World should flip the scales and have MORE Black cast members to balance out the feeling of isolation of being the only one. Taking up most of the airtime in the episode (and about half of the actual runtime for an average Real World episode), “Mad Real World” combines five black roommates from the inner-city with straight laced Chad (in comedian Christian Finnegan’s most infamous role). The results are hilarious, of course, but they also speak to a wider issue over the inclusion of people of color in popular media. Chappelle may have used a childhood favorite TV show to cover up the inherent problems behind this, but in flipping the tropes that The Real World (and other forms of movies and TV) on its head, he made a classic sketch and an even deeper message.

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