Chappelle’s Show is a series that brings with it two feelings whenever you hear it mentioned: 1) memories of the great hilarity that spread across dozens of sketches and two full seasons on Comedy Central throughout the early 2000s; and 2) sorrow that it all ended too soon.
Dave Chappelle, the mastermind behind the series, turned down an estimated $50 million to do a third season. When Comedy Central persisted and did it anyway without his blessing, there was too much bad blood to get the funnyman to ever come back.
Thankfully, Dave is back doing standup, and in a way, his show is back, too.
If you’re a Hulu Plus subscriber, you can now stream all three seasons of Chappelle’s Show for no extra charge.
If you’ve never seen the series before, get ready to laugh. The sketch comedy show features some timely humor that may float over the heads of younger audiences, but for the most part, everything you see is as relevant and bawdy today as it was when it premiered in 2003.
For those of you revisiting the series for the first time in years, you are going to be taken aback by the onslaught of laughs. Yes, there are even more than you remember.
To celebrate the arrival of Chappelle’s Show on the streaming subscription service, The Inquisitr has identified his five best sketches — no easy feat considering pretty much everything in those first two seasons is comedy gold. Let’s get started, but a word of warning: Chappelle is always NSFW.
5. Clayton Bigsby, the Black White Supremacist
Chappelle’s Show played with race relations a lot and got off to a very early start doing so in the inaugural episode. As part of the recurring “Frontline” segment, Clayton Bigsby (Dave Chappelle), the most influential White Supremacist in America, is revealed to be an old, blind African-American who doesn’t realize he’s black.
Raised in a predominantly white area, he was brought up as a white person in a riff on the Steve Martin film The Jerk. Chappelle goes all-in with the character, and the supporting players’ reactions when they find out Bigsby’s true identity are, you might say, explosive.
4. Charlie Murphy’s ‘True Hollywood Story’: Prince
Parodying the popular E! reality series E!’s True Hollywood Story, Chappelle’s Show did its own version based on some of the hilarious tales of Charlie Murphy, Eddie’s brother. One of the funniest involves Dave stepping into the role of Prince for accompanying flashbacks as Murphy tells of the night that his crew got humiliated in a game of basketball over at Prince and the New Power Generation’s hangout (“shirts versus blouses”).
3. Samuel Jackson Beer
It’s not one of the longer sketches that Chappelle’s Show pumped out over its two-season run, but you cannot see Chappelle do his pirate rendition of Samuel L. Jackson while promoting the titular malt beverage and not bust a gut.
2. Knee High Park
Chappelle’s Show meets Sesame Street in this disturbingly hilarious puppet sketch in which Chappelle, Snoop Dogg, and the rest of the crew teach youngsters about STDs and drugs. It’s as awful as it sounds, and equally hilarious.
1. Charlie Murphy’s ‘True Hollywood Story’: Rick James
Sure, maybe it’s the easy way out, but there is a reason virtually everyone in the world knows this sketch. Dave Chappelle’s frenetic performance as Rick James, which plays out over interviews with Murphy and the actual Rick James, was so good that it almost got its own movie, according to SplitSider.
The sketch takes up the entire episode, and it’s worth every moment.
So there you have it, the five best Chappelle’s Show skits. Which ones did you like best, and which ones deserved to be here? Sound off in the comments section!
[Image via Chappelle’s Show screen grab, linked above]