Chappelle's Show Best Sketches
chappelles-show-best-sketches-frontline-clayton-bigsby
2. "Frontline: Clayton Bigsby" (Season 1, Episode 1)
First of all, how incredible is it that this sketch aired in the very first episode of Chappelle's Show? Dave must've had this one saved in his back pocket for a while, because it's a stroke of brilliance: a mockumentary about a blind white supremacist named Clayton Bigsby... who doesn't know he is actually black. It's at once blazingly bold, deeply silly and a good-natured swipe at the essential ridiculousness of racism.
Watch the sketch here.
chappelles-show-best-sketches-i-know-black-people
9. "I Know Black People" (Season 2, Episode 8)
This one isn't a scripted sketch, as such, but a game show where Dave quizzes a wide range of contestants — from a professor of African-American studies to a Korean grocery store worker — on their knowledge of black culture. ("What is a badonkadonk?") Their answers are both hysterical and strangely illuminating... and of course, they're competing to win a gift bag containing bootleg DVDs and menthol cigarettes.
Watch the sketch here.
chappelles-show-best-sketches-internet-real-place
14. "If the Internet Were a Real Place" (Season 2, Episode 6)
One of Chappelle's higher-concept sketches, this one is nearly a Black Mirror episode, with Dave walking through a life-size version of the Internet that's laid out like a shopping mall. It functions both as a 2004 time capsule (Paris Hilton's sex tape! Pop-up ads!) and an oddly innocent snapshot of online life before social media took over every moment of our waking existence.
Watch the sketch here.
chappelles-show-best-sketches-john-mayer
8. "White People Dancing w/ John Mayer" (Season 2, Episode 3)
Here, Dave examines the age-old stereotype that white people can't dance, and discovers they actually can — as long as they hear electric guitar. A trenchant examination of racial diversity follows, with John Mayer providing hot guitar licks for the white folks to groove to. Dave pokes fun at black people and Hispanics, too, and wraps things up with a heartwarming rendition of the Diff'rent Strokes theme song. This is what racial harmony looks like, people.
Watch the sketch here.
chappelles-show-best-sketches-racial-draft
6. "The Racial Draft" (Season 2, Episode 1)
A decade-plus later, this one still stings: a fictional sports-style draft where racial groups take turns claiming celebrities with uncertain ethnic identities — like Tiger Woods, who becomes the black community's top draft pick. (Oof... they are probably regretting that one right about now.) It's a genius conceit that has a lot of fun picking apart just about every stereotype you can think of — the very definition of "equal-opportunity offender."
Watch the sketch here.
chappelles-show-best-sketches-rick-james
1. "Charlie Murphy's True Hollywood Stories: Rick James" (Season 2, Episode 4)
This is kind of like saying Michael Jordan is the best Chicago Bull ever: obvious, maybe, but inarguably correct. You don't have to know the lyrics to "Super Freak" to appreciate Chappelle's loopy impression of the R&B legend, or to be mesmerized by the juicy gossip that Murphy shares about James' outrageous antics... or the real James' very candid recollections. (Cocaine is, indeed, a helluva drug.) This sketch was admittedly overexposed for a while, but it has aged like a fine wine. Sip it, and savor it.
Watch the sketch here.
chappelles-show-best-sketches-the-playa-haters-ball
3. "The Playa Haters' Ball" (Season 1, Episode 9)
If this isn't the best Chappelle's Show sketch of all time, it's absolutely the most quotable, with a gaggle of well-dressed professional haters trading finely crafted insults at a dizzying pace. There are about a million Hall of Fame burns we could cite here, but we're partial to: "What can I say about that suit that hasn't already been said about Afghanistan? It looks bombed-out and depleted."
Watch the sketch here.
chappelles-show-best-sketches-tron-carter-law-and-order
7. "Tron Carter's Law & Order" (Season 2, Episode 5)
Maybe the show's most insightful critique of racial bias, this sketch flips the script on a pair of criminal defendants, treating a white corporate crook like a black drug dealer and vice versa. It's darkly funny seeing the white guy get railroaded and called a "filthy, big-lipped beast," but the highlight is watching drug dealer Tron (yes, from "Reparations 2003") plead "the Fif" on his way to a cushy plea deal.
Watch the sketch here.
chappelles-show-best-sketches-tyrone-biggums-red-balls
10. "Tyrone Biggums' Red Balls" (Season 2, Episode 5)
Friendly neighborhood crackhead Tyrone Biggums was a Chappelle's Show staple, and his finest moment came in a fake ad for the highly addictive beverage Red Balls. (It's "cocaine in a can, baby!") The drink gives Tyrone so much energy, he's able to break into a locked car where a helpless baby is trapped inside... and steal the car's radio.
Watch the sketch here.
chappelles-show-best-sketches-wayne-brady
5. "The Wayne Brady Show" (Season 2, Episode 12)
The famously inoffensive Wayne Brady lets his rough side out in this uproarious sketch, which follows Dave and Wayne on a night from hell. Dave is shocked as the cuddly Mr. Brady guns down a man in cold blood, collects money from street hookers... and uncorks the classic line, "Is Wayne Brady gonna have to choke a bitch?" We still can't look at Wayne hosting Let's Make a Deal without shuddering.
Watch the sketch here.
chappelles-show-best-sketches-wrap-it-up
15. "Wrap It Up" (Season 1, Episode 2)
This ad parody is positively inspired: a little box that plays the "wrap it up" music we hear when awards-show speeches go too long. Think of all the possible uses: during a boring date... a criminal sentencing hearing... even (um) an unsatisfying bedroom session. Admit it: We all could use one of these, couldn't we?
Watch the sketch here.
chappelles-show-best-sketches-wu-tang-financial
11. "Wu-Tang Financial" (Season 1, Episode 7)
This is a brief, one-joke sketch, but it's a great one, imagining a high-end financial services firm run by hip-hop supergroup the Wu-Tang Clan. There's something absurdly enjoyable about seeing a hoodie-clad GZA and RZA sitting at massive oak boardroom tables and dispensing sage investment advice like "You need to diversify your bonds, n—a." In fact, that classic line alone clinches this sketch a place in the top 15.
Watch the sketch here.
chappelles-show-best-sketches-the-three-daves
12. "The Three Daves" (Season 2, Episode 3)
This is Dave doing Boyhood a decade early, with a look back at how he would react to certain situations at age 18 and age 24, versus how he would react now at age 30. It's at once a surprisingly poignant meditation on the maturation process, and a vehicle for silly jokes about the lyrics to "Rump Shaker."
Watch the sketch here.
chappelles-show-best-sketches-prince copy
4. "Charlie Murphy's True Hollywood Stories: Prince" (Season 2, Episode 5)
Fact is stranger than fiction, and this endlessly fascinating tale from Charlie Murphy (RIP) is certainly strange: He recalls him and his friends being challenged to a game of pick-up hoops by none other than Prince. (Yes, that Prince.) What's more, the Purple One and his androgynous bandmates trounce Charlie and his macho pals — and serve them pancakes after. Murphy's narration is mesmerizing, Dave's Prince impression is hilariously droll... and suddenly, we're hungry for pancakes.
Watch the sketch here.
chappelles-show-best-sketches-reparations-2003
13. "Reparations 2003" (Season 1, Episode 4)
This explicitly political sketch — shout-out to Ta-Nehisi Coates! — imagines the ramifications from the U.S. government handing out big checks to the black community to compensate for slavery. (FUBU merges with KFC to form the world's largest corporation; a dice player named Tron passes Bill Gates as the richest man alive.) Bonus points for giving us the Chappelle's Show closing mantra: "I'm rich, beyotch!"
Watch the full episode here.