11 Of The Most Legendary ‘Chappelle’s Show’ Sketches

It’s been 10 years since iconic comedian Dave Chappelle walked away from his hilarious sketch comedy show, Chappelle’s Show. Though the show only aired for three seasons, the sensational sketches remain timeless; forever ingrained in our pop-culture imaginations. Chappelle’s biting criticisms of racism, hip-hop and American culture as a whole, gave him a leg above other comics and helped revitalize Comedy Central. In honor of the legendary comedian and his ground-breaking show, here are the 11 most legendary Chappelle’s Show sketches.

11. A Moment In the Life Of Lil Jon

Air date: February 3, 2004

There was a time in the early ’00s when Lil Jon was one of the biggest names in the rap game. With hits like, the Ying Yang Twinz’ “Salt Shaker” and Usher’s “Yeah!”, Lil Jon was everywhere with his loud shouting and ad-libs. Chappelle, of course, decided to make fun of how absurd the rapper was which made it even more hilarious when he impersonated Jon’s normal voice.

10. White People Dancing

Air date: February 4, 2004

Never afraid to comment on racial stereotypes, Chappelle with the help of his friends John Mayer and Ahmir “Questlove” Thompson decided to try and figure out which instruments motivated different racial groups to dance. As you can see, Black people didn’t seem to keen to hear Mayer on electric guitar.

9. The Player Hater’s Ball

Air date: March 19, 2003

Chappelle didn’t just come up with the Player Hater’s Ball in a vacuum.  Based on The Players Ball founded in the ’70s by pimps across the U.S., Chapelle was inspired to do his own version of the Ball, crowning the “Hater of the Year” in lieu of the “Pimp Of The Year”. Watch the epic sparring between the “most prestigious verbal abusers on the planet.”  We promise you’ll die of laughter.

8. R. Kelly’s “Piss On You”

Air date: March 26, 2003

Chappelle’s Show aired during the height of R. Kelly‘s sex scandal where he allegedly urinated on an underage girl. Never afraid to comment on the wrongdoings in society, Chappelle, eviscerated the R&B singer by remixing Kelly’s “Ignition” and retitling it “Piss On You” Of course, Kelly now claims never saw the sketch…

7. Making the Band

Air date: March 24, 2004

If you were around in the early ’00s then you know of Diddy’s infamous reality show, Making the Band which aired on MTV. The series chronicled Diddy’s antics and his attempts to help mold a hip-hop group whose members were constantly embroiled in drama. Of course, Chappelle decided to parody the series in a hilarious way, taking on the egotistical hip-hop mogul himself.

6. The Mad Real World

Air date: February 26, 2003
MTV’s Making the Band wasn’t the only reality show that Chappelle parodied. The comedian also took on MTV’s The Real World , commenting on the fact that Black people who often appeared on the majority white shows were often made out to be crazy instead of the environment itself being a terrible one to be in,

5. Tyrone Biggums

Air date: March 12, 2003

Tyrone Biggums was one of Chappelle’s most long-running and classic characters on Chappelle’s Show. Tyrone was the epitome of a crack head who would do anything to get his hand on a dollar to buy his drugs. Tyrone was always a fan favorite.

4. The Racial Draft

Air date: January 21, 2004

To this day The Racial Draft is called one of the best sketches of all time. Focusing on the racial identity of America and how people latch onto celebrity figures. The biggest names in sports and entertainment were up for drafts as the races argued over who they wanted.

3. Frontline: Clayton Bigsby

Air date: January 22, 2003

Dave Chappelle opened the “Frontline: Clayton Bigsby” sketch by saying, “I still haven’t been canceled yet, but I’m working on it. And I think this next piece might do it. This is probably the wildest thing I’ve ever done in my career and I showed it to a black friend of mine, and he looked at me like I had set black people back with a comedy sketch. Sorry…” What came after was a stunning sketch about Clayton Bigsby, a blind, African-American white supremacist…the most absurd (and hilarious) idea that Chappelle ever conceived.

2. Charlie Murphy’s True Hollywood Stories – Rick James

Air date: February 11, 2004

Because of  Chappelle’s Show and Charlie Murphy‘s True Hollywood Stories, you can’t think of Rick James without wanting to yell, “I’m Rick James, bit*h!” Chappelle nailed it as the enigmatic “Super Freak” singer while Murphy reflected back on his love of the ’80s and his times with his younger brother.

1. Charlie Murphy’s True Hollywood Stories – Prince

Air date: February 18, 2004

Charlie Murphy’s True Hollywood Stories didn’t end with Rick James. Perhaps the most iconic Chappelle’s Show sketch of all time revolves around the late icon Prince, a game of basketball and some pancakes. The best part about the entire thing is the fact that the late Purple Rain singer confirmed all of this did actually happen and that he adored Chappelle and Murphy for doing the sketch. He even released the song “Breakfast Can Wait” in 2014, which was inspired by the sketch using Dave Chappelle as the single’s cover art.

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