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.
Follow @hprocksoff
