Despite not having aired an original episode in almost seven years, few shows are universally beloved as Chappelle’s Show. This is particularly great because few shows have shown as much love towards hip-hop than Dave Chapelle’s satirical masterpiece on the intersection of race, pop culture and American comedy. Perhaps more than any other comedian in history, Dave Chappelle has been hip-hop’s comedian. Versed in the culture and minutiae of a true hip-hop fan, Chappelle’s Show is coded in the language and culture of rap music.
Over the too brief 28 episodes of the series, hip-hop played a vital part in the show’s appeal. Whether, it was the numerous guest performances by rappers on the show or appearances by rappers and artists in the show’s many classic sketches, hip-hop was present in one of the 2000′s shining examples of American comedy.
XXL brings to you a collection of the many the greatest guest appearances by hip-hop over the years on the show. These are the moments that made Chappelle’s Show, one of the defining shows in hip-hop history.