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TDS Staff Picks: Favorite Chappelle’s Show Sketch

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There’s so many to choose from.

Dave Chappelle’s Show 2nd Season Launch Photo by Sylvain Gaboury/FilmMagic

In light of the recent announcement that all college sporting events are suspended/canceled for the foreseeable future, we’ve decided to try to bring some sense of levity, and distraction from the real world that sports invariably did for decades. With no USF spring football, baseball or softball content to churn out, we’ll make do with whatever comes to mind. Enjoy.

It’s amazing how Chappelle’s Show took over the public conscience almost immediately after the first episode aired on January 22, 2003. Every conversation, someone peppered in a Chappelle’s Show quote or reference, which turned into a 10-minute reenactment of our favorite bits. While the show only lasted 28 episodes, the cultural impact remains over 17 years later. We’ve decided to pick our favorite sketches. There may be some duplicates, and that’s OK.

Let’s start the show.

The Racial Draft - Season 2 Premiere, by Nathan

“I’ve always wanted to say this...FOR SHIZZLE”

Draft picks:

  • Black delegation: Tiger Woods
  • Jewish delegation: Lenny Kravitz
  • Latino delegation: Elian Gonzalez
  • White delegation: Colin Powell, and Condoleezza Rice for OJ Simpson.
  • Asian delegation: Wu Tang Clan

This entire sketch is perfection, and a clear sign that Dave Chappelle had found his sweet spot as an entertainer, and that season two was going to be an absolute banger. When Chappelle says “Now wait just a God Damn minute Rondell” after the Black delegation, played by Mos Def, tries to take Eminem as part of the trade for Powell had me rolling on the floor. The White delegation throws in O.J. Simpson to keep Eminem, they shake hands and walk away.

The commentators may have been the funniest part of the sketch with Chappelle breaking the news that Tiger Woods has lost all endorsements after becoming 100% black, the total confusion of the White delegation’s pick of Powell, to Bill Burr and the other guy (I’m not looking up his name) quietly celebrating getting rid of Simpson all made for a fantastic sketch.

The World Series of Dice- Season 2, Episode 7, by Seth

“When I leave, come together like butt cheeks”

In 2003, ESPN began airing the World Series of Poker. It exploded in popularity and launched unknown poker players into the public consciousness. Its popularity also helped to spawn one of my favorite Chappelle’s Show skits: The World Series of Dice.

The World Series of Dice is presented as a large, sporting event complete with two announcers (Bill Burr and Robert Petkoff) and the Monday Night Football theme. In actuality, it’s a game of dice being played in the Marcy Projects by four competitors:

  • Grits n’ Gravy -Kansas City, MO
  • Phyuck You -Far East
  • Leonard Washington -A little town called none of your business
  • Ashy Larry- Marcy Projects

The absurdity of the characters, from their names to their looks, melds with the absurdity of the presentation and the deadpan seriousness of the announcers to create something special. The whole skit gets taken to a new level when the game is robbed by “local thug” Rodney “Quills” Dinkins, who breaks in and demands that everybody “get butt naked”. From there it builds to a beautiful crescendo where Leonard Washington stares down Quills like a gunslinger in the Wild West. Quills calls his bluff and a telestrator -style breakdown of the shooting includes the following exchange:

Burr- “You noticed how he shot him below the waist, so it’s not attempted murder. That’s very intelligent on Quills’ part”

Petkoff- “Quill knows the Law”

The Sketch ends with the announcers signing off as they are stripping off their clothing and being robbed. The sketch is a great blend of absurdity and parody with great performances throughout.

Black Bush - Season 2 Finale, by Nick

Season two of Chappelle’s Show may be the greatest season of any comedy show ever. Racial Draft, the Rick James and Prince skits, the Lil’ Jon skits, the Wayne Brady episode, it’s a murderer’s row of some of the funniest television to ever hit the airwaves and had myself and my friends dying week-after-week in middle school.

So it’s only right that the season ended with a skit as over the top as Black Bush. Early 2004 in the midst of the Iraq War and W’s first term, Dave takes on the roll of the 43rd president to highlight the absurdity of the administration at that point in time. We get moments like Jamie Foxx showing up as Black Tony Blair, the Black Head of the CIA, played by Mos Def, holding yellow cake in a “special CIA napkin”, the president challenging the U.N. to sanction him with their non-existent army, “M.A.R.S, Mars bitches,” and so many other quotables that I recite to this day.

It also gave us this...

“What? Huh, oil? Who said something about oil, bitch he cooking? Oil...COME ON Y’ALL, LET’S GET OUT OF HERE!”

Black Bush- Season 2 Finale, By Jamie

Picking the best Chappelle’s Show sketch is really hard. There are at least 10 Hall of Fame-level sketches, and every time you think you’ve settled on the best, you remember another one and you have to start all over again.

First I thought I would go with the Wayne Brady sketch, because I love watching actors playing way, way against type. I also thought about the Racial Draft (which doesn’t really hold up anymore), both of Charlie Murphy’s True Hollywood Stories, all three When Keeping It Real Goes Wrong sketches, the Player Haters’ Ball, The Mad Real World, the Tyrone Biggums Fear Factor sketch, the Three Daves sketch, Clayton Bigsby, even the reparations sketch, and the Trading Spouses sketch.

The best one, though, is clearly Black Bush. When you write one sketch that spawns TWO memes that are still going strong 16 years later (“Mars, bitches” and the GIF of Dave knocking over the water and his crew scattering from the Cabinet room), that just has to win. It does.