Dave Chappelle has been aggressively plugging himself into the pop culture zeitgeist so much over the past few years that it’s hard to believe that he basically disappeared for a decade after reaching the top of the comedy world. Chappelle’s first trip up fame mountain came courtesy of Chappelle’s Show; as popular as his stand-up is, his sketch series is still what he’s best remembered for. Comedy Central’s flagship show, which aired from 2003 to 2006, produced some of the most memorable sketches of all time. But perhaps what it’s remembered for equally as much is that it was the show that drove Dave away from the limelight after three seasons, rarely to be seen for a solid decade. Since returning regularly to the limelight in 2016, Chappelle has been cranking out Netflix specials, hosting SNL, collecting the Mark Twain Prize for American Humor from the Kennedy Center, and even had a small but pivotal role in Bradley Cooper’s A Star Is Born.
Thanks to Netflix, HBO Max and CBS All Access, generations old and new can either re-visit or view for the very first time all three seasons of Chappelle’s Show. Having revisited the show myself, I got to see all the ways in which Chappelle has changed as a comic, but even more so, all the ways he’s actually stayed the same. In the first episode, Chappelle addresses the audience saying, “welcome back to the show, I still haven’t been canceled yet, but I’m working on it.” In the very next episode, he comes on stage to tell the crowd, “we’re considered controversial, you can’t say anything on TV anymore.” Based on a moment where he called out the audience at his most recent SNL set for groaning at a joke, it seems like 2003 Dave Chappelle and 2020 Dave Chappelle would get along just swimmingly.
?His current standing in the industry may be a divisive one, but the truth is Dave Chappelle crafted one of the funniest sketch shows ever to appear on television. Now thanks to the streaming gods, they are available again for our enjoyment. Here are 5 great sketches that capture the essence of the show and reminds us just how iconic Chappelle’s Show really was.
Of all the Chappelle’s Show quotes my college friends and I shouted at each other, this sketch had the most. Everything from “Game, blouses!” to “Assemble your crew. I’ll be outside” is hysterically delivered by Chappelle playing Prince. The way Charlie Murphy tells the story of this basketball faceoff is the comedy gold that brings it all together. Just how iconic is this sketch? I saw it shared non-stop the day of Prince’s passing.
While this one might not have much meat on the bones, it’s without a doubt the hardest I have laughed during this entire show. It’s a classic case of a sketch completely flipping the persona of a celebrity that everyone “thinks” they know. Turn the lovable Wayne Brady into a wild, psycho killer, and you have me in stitches.
One of my favorite things Chappelle ever did was impersonate celebrities in his sketches that he looked and sounded nothing like. It’s his mannerisms and commitment to the character that sells it and makes it a joy to watch, even if it’s just Dave in a wig. Nothing drives this point home more than Chappelle as Samuel L. Jackson selling Samuel Jackson beer.
A sketch only somebody with Chappelle’s talent and experience could pull off. This is a very simple and easily understood premise, but one that could go so wrong in the hands of other sketch shows during this time. Find some pop cultural icons who the public isn’t quite sure what their exact race is and set up an NFL style draft complete with commentators. It is without question one of the most memorable sketches just based on the idea alone.
A fake commercial for a copy store where the employees treat the customers like scum of the Earth? Sign me up. Not only does PopCopy capture the show’s silly sensibilities the most, it’s also one of the better commercial parodies to come out of any sketch show. Including this sketch in the very first episode sets the audience’s expectation for the type of rude, off the wall, and sometimes gross-out humor that they can expect in the show going forward.
Chappelle’s Show is now streaming on Netflix, HBO Max, and CBS All Access.
Christian Becker is a writer and comedian based out of NJ. You can follow him on Twitter at @TheAmazingBeck.