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Top 10 'Chappelle's Show' Sketches

The best 'Chappelle's Show' sketches make us wish this series was still on air.

You can't have a conversation about sketch comedy series without mentioning this comedian's short-lived show. Join WatchMojo.com as we count down our picks for the "Top 10 Sketches from Chappelle's Show."

For this list, we’re taking a look at the defining sketch from this acclaimed comedy show that was never afraid to tackle society’s most controversial hot topics.

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#10: “The Niggar Family”

When it comes to racial slurs, is it the word itself that makes it offensive, or the context? Chappelle, being the inquisitive host he was, decided to explore this concept the only way he knew how. This controversial sketch features a suburban white family that just so happened to carry the last name Niggar, which as you can imagine, makes for some more than interesting scenarios and double entendres. Behind the comedy, the sketch speaks volumes on our society’s social conditioning and what we consider politically incorrect.

#9: “Making the Band”

Reality TV shows do a pretty good job at making fun of themselves on their own, but that doesn’t quite save it from Chappelle’s critique. This sketch parodies hip-hop mogul P. Diddy’s MTV series Making the Band, and hilariously sums up the show’s numerous shortcomings. The selected band members never seem to get to record any music, and their boss’ random assignments do nothing but lead the team astray. The comedic depiction of the cast is what really puts us in stitches, and allows us to meet the self-proclaimed best rapper of all time.

#8: “A Moment in the Life of Lil Jon”

When it times of great despair, sometimes you’re your own best listener. In this sketch, audiences look into the mind of one of hip-hop’s greatest hype men. Along with posing as the performer, Chappelle gets the real Lil Jon to appear on the show and illustrate an intimate phone conversation with himself. Amid all the various “Yeah!,” “HWHAT?!,” and “O-kay!’s,” Lil Jon unveils some of his deepest disturbances and shows a side of himself not commonly seen. The two end their phone call abruptly, and while they couldn’t hear each other, we’re sure they both understood each other perfectly.

#7: “The Wayne Brady Show”

Have you ever found out who your friend really was once it was too late? No? Just Dave? After seemingly taking over Chappelle’s Show, Wayne Brady shares his and Dave’s eventful night out. Contrary to the joyful and charismatic straight arrow Brady portrays on television, the comedian is soon revealed to be homicidal pimp with a short temper. Throughout their drive, Brady coerces Dave to take drugs, to become an accessory to murder, and to listen to his delusions of grandeur. Just when you think you know a guy.

#6: “Tyrone Biggums - Red Balls Energy Drink”

Make no mistake, drug addiction is a serious problem, and Chappelle opted to show everybody just how severe it could be with the conception of this character. Tyrone Biggums is much like your everyday community member, but he just so happens to be addicted to crack. He’s often comically depicted as a hygienically challenged homeless man with an exaggeratedly high voice. His various skits have shown him sponsoring a cocaine-infused energy drink, speaking to a elementary class on the dangers of the drug, being featured on Fear Factor, and even attending a less than successful drug intervention. “Shazam!”

#5: “Reparations 2003”

If you’re a fan of this comedian’s work, then you recognize how keen he is on hypotheticals. This sketch entertains the idea of how the U.S. would react if African Americans received one trillion dollars in reparations for slavery. As reported by anchorman Chuck Taylor and his team, the country gets flipped on its head as various stocks on Wall Street skyrocket, crime drops to zero percent, and Bill Gates gets dethroned as the world’s richest man by Harlem resident Tron.

#4: “The Racial Draft”

Racial ambiguity can be a beautiful thing, but oftentimes confusing. In an attempt to resolve some of our nation’s biggest questions regarding our biracial athletes and celebrities, Chappelle hosted the first, and most likely only ever, racial draft. In this, we see star golf player Tiger Woods getting drafted into the black community, Lenny Kravitz becoming fully Jewish, and even more ridiculous incidences, such as hip-hop group the Wu-Tang Clan becoming accepted by the Chinese delegation.

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

Prince is revered as one of most respected musical talents alive, but would you have ever imagined him to have some slick moves on the court? Charlie Murphy didn’t, as he returned for another segment of True Hollywood Stories, to recite the tale of the day he met Prince. Murphy recalls the two meeting at a nightclub before retreating to pop star’s personal pad. In the spur of the moment, Prince challenges Murphy and his crew to a game of basketball that he wouldn’t soon forget. Underestimating Prince and The Revolution, Murphy gets schooled Purple Rain-style before being served breakfast by the winning squad.

#2: “Frontline: Clayton Bigsby”

Most comics prefer to tread lightly onto the scene with their television show debut, but Chappelle isn’t most comics. With his first episode, Chappelle introduces yet another hilarious hypothetical of a blind African American man that is raised as a white supremacist. When he finally agrees to an interview with Frontline, Clayton Bigsby’s true identity finally reaches the masses. His family and peers have kept the secret from him for his own protection and for the good of the movement. However, he finally makes his big reveal at a KKK rally where the reactions are priceless.

Before we unveil our pick for top Chappelle’s Show sketch, here are a few honorable mentions:

  • “Samuel L. Jackson Beer”
  • “I Know Black People”
  • “R. Kelly’s “Piss On You” Music Videos”
  • “Better in Slow Motion”
  • “The Playa Hater’s Ball”
  • “Kneehigh Park”

#1: “Charlie Murphy’s True Hollywood Stories - Rick James”

Hollywood can be a crazy place, and it was this defining sketch that let us know just how crazy it got for Charlie Murphy in the 80s. Being Eddie Murphy’s brother allowed Charlie to rub shoulders with a lot of prominent celebrities of that era, such as R&B legend Rick James. Murphy’s story highlighted the singer’s insufferable behavior and drug problem, and how he’d often have to “check him” once he got out of line. This single sketch shaped the show into what it became and is also credited for coining Chappelle’s most famous line. [“I’m Rick James bitch.”]

Do you agree with our list? What Chappelle’s Show sketch makes you wish Dave would return to television? For more comedic Top 10s published daily, be sure to subscribe to WatchMojo.com.

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