My Five Favorite Chappelle’s Show Sketches

March 25, 2021

Recently, some of my Twitter friends and I discussed what some of our favorite Chappelle’s Show sketches are. Many all-time greats with all-time classic characters were mentioned, from Ashy Larry to Clayton Bigsby to Tyrone Biggums. In lieu of our late-night chat, I present you my five most favorite Chappelle’s Show sketches.

5. “Tron Carter’s Law & Order”

Coming in at the fifth (or should I say “fif”) spot is “Tron Carter’s Law and Order.” This sketch is one of my all-time favorites and in my opinion one of the most underrated sketches in the three seasons of Chappelle’s Show. You can watch the whole thing uncensored on YouTube. The sketch features Dave Chappelle’s recurring cocaine dealer character Tron Carter, comparing his process for being arrested and trialed to that of a white CEO charged with multiple offenses of financial fraud. The twist of the sketch is that it takes place in an alternate universe where Carter faces the judicial system that a typical white CEO would get along with its benefits, while the CEO faces the judicial system as if he were a black man, facing unfair and unjust punishment. This sketch is sometimes overlooked as it is in the same episode as Charlie Murphy’s Prince story (we will get to that) and Tyrone Biggums’ Red Balls energy drink, the two sketches featured in the episode’s title. The sketch features comedian Rick Crom as the CEO’s public defendant and Bill Burr does an excellent job playing the lead detective. Be prepared to read Bill Burr’s name more as we move along in the list.

4. “World Series of Dice”

The announcing team of Robert Petkoff and Bill Burr commentate the eighth annual World Series of Dice, live from the Marcy Projects in Brooklyn. This sketch features Eddie Griffin as Grits n’ Gravy, Chappelle as recurring character Leonard Washington, and Donnell Rawlings as hometown player Ashy Larry. Rounding out the competitors is Chappelle’s Show regular Yoshio Mita as Phyuck Yiu. All four do a spectacular job with their competitive dialogue, including some great smack-talk early from Washington to Ashy Larry. Charlie Murphy makes a great appearance at the end, and Petkoff and Burr make the whole thing seem like it could be a real broadcast. Here is the YouTube link for the full uncensored sketch.

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

One of two “Charlie Murphy’s True Hollywood Stories” comes in at the three spots. This sketch is a nice blend of Murphy’s real takes on the wild world in the 80s, Chappelle doing a tremendous celebrity impression, and a solid supporting cast of characters. The audience is into the sketch from the beginning with the reveal of Murphy’s Jheri curl and the slow pan up to Chappelle as Prince. Chappelle nails his Prince impersonation, with the slight audible noises throughout really sealing the deal. The Revolution members do a great job in their roles, and we get a hilarious line from Donnell Rawlings, saying through his teeth “Man I’m not on your team” after a love tap from Prince. This sketch is also uncensored on YouTube.

2. “Racial Draft”

Petkoff and Burr are back on the call, this time joined by Chappelle. In another sports production parody, this sketch spoofs on the NFL Draft by using various races drafting different celebrities. The sketch opens with the black delegation’s number one pick, Tiger Woods (Chappelle), presented by Mos Def’s character Rondell. The sketch features many hilarious jokes playing on various perceived racial stereotypes, and the tension at the announcer table between Chappelle and Burr is hilarious throughout. From Rondell and Tiger Woods with the number one pick to the entire Wu-Tang Clan being selected as the final pick to the Chinese delegation, this sketch is an A+. Here is the YouTube link for the full uncensored sketch.

Honorable Mentions:

“Samuel Jackson Beer” – A parody of Samuel Adams, with Chappelle playing Samuel Jackson in a colonial outfit. Jackson lays his profanity-laden promo on an unsuspecting Bill Burr, making this sketch short and sweet.
“Reparations” – A news segment about the government permitting reparations to all African Americans in the United States. Dave Chappelle plays both white news anchor Chuck Taylor and previously mentioned Tron Carter, who plays a game of dice to add to his status as richest man in the country. My favorite part of the sketch is Taylor listing the impact of reparations on various stocks, including Sprint, KFC, and the gold industry.
“Trading Spouses” – A look on the first ever interracial version of the popular reality show. Chappelle plays both Todd, the white guy, and Leonard Washington from the dice sketch.

1. “Charlie Murphy’s True Hollywood Stories – Rick James”

Undoubtedly the best Chappelle’s Show sketch. Not only do you get to hear Charlie Murphy’s real life takes on the world of the 80s, but you also get to hear from Rick James himself. Just like the other Murphy story, the audience is loud from the beginning once Chappelle’s costume is revealed. The most quotable sketch is so jam packed with great content, there two commercial breaks before the whole story is finished. Chappelle and Murphy are outstanding in this sketch, and Rick James is intentionally (and many times unintentionally) hilarious. The favorite line of mine and my dad’s is after Eddie Murphy says Rick James needs help after they beat him up when Charlie says, “We just gave him some help.” Here is the link for the YouTube clip.

It was tough to nail this list down to just five sketches, so I encourage you to discuss sketches you like that I may have missed. I have loved Chappelle’s Show since my dad got me into it with reruns on Comedy Central. It is my all-time favorite show, and I am glad to share my favorite moments from my favorite show!