The 10 Best Dave “Chappelle Show” Skits Ranked

In two-and-a-half seasons, comedian Dave Chappelle’s The Chappelle Show created the best comedy sketches of all time. Dave Chappelle made fun of topics that no one in America would dare touch — then and now. He tackled topics of race, identity, politics, and stereotypes in a candid brand of comedy that America desperately needed (then and now).

Ranking the shows legendary skits is no easy task. Many of the show’s jokes like “Charlie Murphy’s True Hollywood Stories” and “Clayton Bigsby” are inseparable from pop culture itself. In other words, someone will always be mad when ranking Chappelle’s greatness.

Either way, here we go.

10. “The Wayne Brady Show”

“Is Wayne Brady going to have to choke a bitch?”

There’s nothing better than the first time watching this skit. It might be one of the most subversive comedy sketches of all time.

Depending on the day, “The Wayne Brady Show” can be a top 5 skit. Sometimes it just hits right.

Unfortunately it lacks replay-ability that other classic sketches have.

9. “Charlie Murphy’s True Hollywood Stories: Rick James”

“Bitches! Come over here and have sex with Charlie Murphy”

At this point you would think the “Rick James” sketch is played out. It’s referenced anywhere and is the gateway drug for many Chappelle Show fans. However, this skit holds up no matter how many times you watch it.

And who knew that Charlie Murphy would be a natural storyteller and comedian. I guess it runs in the family.

8. “Playa Hater’s Ball”

“Why don’t you click your heels together three times and go back to Africa.”

This is the all-star lineup for the Chappelle Show. Charlie Murphy and Donnell Rawlings to Ice-T and the late, great hater Patrice O’Neal all put in MVP performances.

“The Playa Hater’s Ball” is one of those skits that only Dave Chappelle could have come up with.

7. “Reparations”

“I’m gonna reinvest my money into the community…SSSYYYKE”

Talk about a sketch that stands the test of time. If Dave Chappelle released “Reparations” today, he’d no doubt be canceled and labeled an alt-right white nationalist.

It’s jokes like these that only 1 percent of the population would ever utter out loud. This show and South Park made Comedy Central the most anti-politically correct network on television.

6. “Making The Band”

“Alright, the only way I’ll open the studio now — y’all have to walk up to the Bronx and get breast milk from a Cambodia immigrant. I only drink the finest of breast milks.”

In this criminally underrated sketch, Chappelle parodies P. Diddy’s MTV show Making The Band. Dave took so many shots at Diddy’s entitled rich-boy attitude.

With the actual cast of the show appearing, and Dave’s stellar performance as the infamous Dylan, this makes for an unforgettable skit.

5. “Racial Draft”

“We the black delegation requests Eminem”

Dave Chappelle, Bill Burr, and the Wu-Tang Clan — what more do you need?

On it’s premise alone, the “Racial Draft” is a top five Chappelle Show skit. But Chappelle has plenty of surprises including the Jewish people claiming Lenny Kravitz and the Asians taking the Wu-Tang Clan.

It’s so genius it makes you want to see a real life one.

4. “I Know Black People”

Dave: “How will black people rise up and overcome?

White Female Cop: “Get out and vote.”

[buzzer sounds]

Dave: “That’s incorrect!”

Another hidden gem in Chappelle’s stellar group of skits. The key to the game is to ask irreverent and audacious questions about black culture to a wide array of people.

The comedic timing, like many of Chappelle’s greatest skits, is perfect. And the impromptu nature of this one makes for a legendary 5-minute burst of comedy.

3. “Charlie Murphy’s True Hollywood Stories: Prince”

“Game. Blouses.”

Charlie Murphy’s story about first meeting Prince and The Revolution is unimaginable.

There’s smoke machines, basketball, and pancakes. I’ll say it again, what more do you need?

2. “The Niggar Family”

“He sure is one lazy Niggar.”

I can’t believe Chappelle went there. This is another sketch that would likely burn down the internet if he released it today. And goddamn is one of Chappelle’s best.

This sketch sits in the hall of fame with Randy Marsh screaming out the n-word on South Park, or pretty much the entirety of the Boondocks, and many other adult show classics that went further than anyone ever imagined.

It would be number one if it weren’t for one that went further…

1. “Frontline—Clayton Bigsby”

Frontline: “What exactly is your problem with African Americans?”

Bigsby: “Well fella, how much time you got?”

This is one of the greatest comedy sketches of all time. Moreover, it appered in the first episode of the Chappelle Show. Talk about setting the tone.

In under 10 minutes Chappelle will have you rolling on the floor from laughter. Additionally, it’s most likely the best example of showing just how moronic racism and xenophobia are.

Incredible satire will do that.