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.
My 5 Favorite Rapper Cameos On “Chappelle’s Show”