Dave Chappelle: One of Hip-Hops Favorite Comedians

Matthew Spence
4 min readMay 19, 2020

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Dave Chappelle is hands down one of the best comedians of our time, and if not, the best comedian of all stand (but that’s debatable). Laying the groundwork with stand up specials to establishing his legacy with his classic & beloved sketch comedy show “Chappelle’s Show”, which gathered a huge fan base especially Hip-Hop culture. Hip-Hop has gone on to express love for Dave and the feeling is mutual with him as well; Dave has expressed his love for rap throughout his career, to the point where he is Hip-Hop.

On “Chappelle’s Show”, numerous skits were revolving around an underground rapper who’s deaf in one ear, hip hop moguls promoting out of the ordinary products, and so on. The show also had appearances and cameos from rappers & hip-hop moguls including frequent guest/performer Yassin Bey, who then was known as Mos Def, Q-Tip of A Tribe Called Quest, Redman, RZA & GZA of the Wu-Tang Clan, The Roots and etc. During the entire series (excluding the 3 lost episodes), many musical guests performed at the end of the show. In fact, in season 2 episode, Common & Kanye West performed their song “The Food”, that performance went so well that Common used the live version from the show on his critically acclaimed 2005 “Be” instead of the original studio version of the record. Kanye West would make his first television performance ever a year a before in 2003 on Chappelle’s Show, with him performing “Two Words” featuring Mos Def & Freeway. Going beyond the show, in 2005, Dave held a block party in Brooklyn, N.Y. with performances by Black Star, Common, The Roots, Kanye West, Erykah Badu, & reuniting The Fugees. Soon to be documented for his properly titled film “Dave Chappelle’s Block Party”. Adding to this is he is also somewhat being an honorable member of the Soulquarians and Native Tongues due to his close ties with The Roots, Common, Erykah Badu, De La Soul, Yasiin Bey & Talib Kweli.

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On Raps end of the bargain, many rappers gave gone on to reference Dave Chappelle and “Chappelle’s Show” on multiple occasions. Those rappers include Lil’ Wayne, J.Cole, Ghostface Killah, Tyler, The Creator, & so on. Most notably, the show’s most famous sketch, “Charlie Murphy True Hollywood”, in particular his story involving run-ins with legendary funk singer Rick James. Notable references include: Pusha T Trouble on my Mind “Rick James said Cocaine is one helluva drug” to A$AP Rocky’s verse on Famous Dex’s Pick It Up “What the face say to the fist? (I’m Rick James, bitch!)”; to Earl Sweatshirt in his verse on the Danny Brown song “Really Doe”, where he says “I’m at your house like, “Why you got your couch on my Chucks?”. Past the skit references, Hip-Hop still mentions Dave; J. Cole on his song Runaway from 2013: “In our thoughts, if I follow my heart to save myself, Could I run away from fifty-mill like Dave Chappelle?”. On the skit “Fin” from The Odd Future Tape, Tyler takes the time to thank everyone from friends, family, and inspiration one of those he lists is Chappelle himself: “……Adult Swim, uhh Fresh Prince, Magic School Bus, Reading Rainbow, 90’s Nick, Dave Chappelle, Chris Rock, Eddie Murphy, Will Smith….” In a piece with Teen Vogue from 2017, Chance the Rapper elaborated on his admiration of Dave saying: “I would largely attribute my identity — as it relates to music labels and corporate music giants — to Dave Chappelle and his relationship to and firm standing in Hollywood”.

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Now over a decade later from a hiatus, deeply missed, Dave Chappelle is back in the light with numerous successful Netlfix Standup specials and the love continues to spread. At the 60th Annual Grammy Awards, Dave Chappelle was there, to win Best Comedy Album, but to also be apart of Kendrick Lamar’s opening performance by giving quick speech interludes & to be the one to present the Best Rap Album award (but he couldn’t have done it without first shouting out to one of his favorite groups A Tribe Called Quest, who people say were snubbed). Sure, Dave Chappelle isn’t the first comedian nor only comedian Hip-Hop loves (e.g. Chris Rock, Eddie Murphy, Richard Pryor, Bernie Mac), however, over 20 years in stand up not only has a place in comedy but a place in Hip-Hop.

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Matthew Spence
Matthew Spence

Written by Matthew Spence

What's up, I love to write about music and other pop culture topics I enjoy. Hopefully, I'll go far with this!

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