During his show’s two-year run (many of us don’t count the third season), Dave Chappelle used his clout in the entertainment industry to reel in rap’s A-listers for weekly musical segments. While watching Snoop rap “Deep Cover” with Tyrone Biggums was cool to see, the real benefit of bringing such names to the show were often found in skits. These segments showcased the featured rappers goofing around with Dave. From playing fictionalized versions of themselves to made-up characters, the following are some of my favorite Chappelle’s Show skits to feature rappers. As always, feel free to drop your two cents in the comments.
1. Snoop Dogg – “Kneehigh Park”
Key Quote: “I got so much puppet ass, it could be from anywhere.”
A twisted take on Sesame Street. Featuring a cast of degenerate puppets, “Kneehigh Park” showcased the Dogfather as the voice behind Dave Chappelle’s STD-infected puppet buddy. Q-Tip even stops through at the end, singing a nursery rhyme about wrapping up before hitting the sheets. Exposing a wide-eyed group of kids to the horrors of sex and drugs will never be funnier.
2. Big Boi – “Giving Up The Show”
Key Quote: “We playing on the moon, bitch. Peace.”
Desperate to prove that he still matters after giving up his show, Dave calls Big Boi to hang out. In about a minute’s worth of air time, Big Boi steals the scene, his reluctance to be seen with an out-of-work Chappelle so hysterical. Nick Cannon also makes a surprisingly funny cameo, if only because of his willingness to be a punchline.