Growing up around the time that Chappelle's Show was on the air, it was like a cult. Literally the moment that a new episode aired, you'd have any number of hilarious new quotes to throw around with all your friends. Dave Chappelle invented memes on a nightly basis for a generation of teens, and it was like a national tragedy for us when he announced in 2006 that he was hanging it up and leaving the show.
To this day, you can still go to a party and see a DVD of the show on TV in the background. Its popularity remains unabated. Some of the most frequently quoted and best sketches on the show were ones where Chappelle lampooned popular musicians, and so it seems fitting that in light of the recent announcement that Chappelle will be performing in Houston that we take a look back at those.
5. R. Kelly's "Piss on You" Music Videos Maybe the only thing worse for R. Kelly's public image than the sex tape which it was making fun of, Chappelle pretty much cemented Kelly's guilt to millions of viewers as he showed them damning evidence: Kelly's own music.
Of course, it's not a real song, but it was a damn good parody. It also hit the nail on the head about how Kel's music could be used against him in a public forum. After all, a guy writing sex songs all day getting embroiled in a sex scandal isn't going to fare well. Well, unless you're R. Kelly since he was found not guilty.
4. Making the Band If anyone remembers how utterly stupid Diddy's short lived TV show on MTV, Making the Band, was, then you'll really appreciate Chappelle and crew taking the piss out of it here.
Luckily, if you don't remember it, it's still really funny. Chappelle nails Diddy's attitude and vibe, and the ridiculous stuff he comes up with for the contestants to do is a dead on parody of pretty much any reality show in the last decade.
3. Tupac is Still Alive It was unfortunate when Comedy Central chose to air the last few episodes of Chappelle's Show that Chappelle had filmed, effectively burning bridges with the star, but it did gives us a few more classic sketches to quote for the next few years.
One of the best sketches to come out of it was this amazing parody of the "Tupac lives" rumors, featuring Chappelle's impression of Tupac which could probably fool a casual fan on first listen.
2. Charlie Murphy's True Hollywood Stories -- Prince Prince may seem like an easy target, but Chappelle and Charlie Murphy took the high road on this one. As clear fans of Prince, the two managed to write a sketch that avoided any of the simple Prince jokes others might use.
Instead, the sketch draws its humor largely simply from playing Prince straight, in pretty much exactly the way he behaves in real life. Prince's behavior and attitude needs no exaggeration or over-the-top parody. Prince is just funny in and of himself, which luckily Chappelle and Murphy understood enough to create this legendary sketch.
1. Charlie Murphy's True Hollywood Stories -- Rick James Maybe the ultimate Chappelle's Show sketch, "Rick James" not only became forever associated with the show afterward, but it practically made Charlie Murphy a household name.
The sketch's quotes may have grown grating over the years to hear repeated endlessly and totally out of context, but it cemented the show's legacy and still holds up today. This sketch will go down in history as one of the all-time greatest to ever air on television.
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