‘Chappelle’s Show,” the genius comedy show that introduced a number of catchphrases into the public lexicon and became both a blessing and a burden to its creator, Dave Chappelle, is best known for its standout sketches and characters.
Just the words “African-American KKK member Clayton Bigsby” or “Wayne Brady gunning down people from the front seat of his car” are enough to make people laugh.
The first five dates of Chappelle’s upcoming run at Radio City Music Hall are the comic performing solo, but the shows on June 23 through 26 feature collaborations with Nas, The Roots, Erykah Badu and Janelle Monae, among others.
Going back to those Comedy Central episodes, Chappelle has always incorporated music into his work, whether it was guest performances by artists at the end of the show or, on occasion, appearances in sketches.
amNewYork broke out the DVDs for the first two seasons of “Chappelle’s Show” and put together a list of the best collaborations between Chappelle and the music world — and no, his impersonation of Prince does not count.
The Player Haters Ball (featuring Ice-T)
The Original Gangster hosted the Haters Awards, threatening that the next heckler would be shot. Unsurprisingly, the crowd seemed to believe him.
Wu-Tang Financial (featuring RZA and GZA)
Three words: Diversify. Yo. Bonds.
Charlie Murphy’s True Hollywood Stories: Rick James (featuring Rick James)
One of the best-known sketches of the show’s run would have worked just based on Chappelle’s unhinged impression of the “Super Freak” singer. But the interstitial appearances of the actual James yield the show’s biggest catch phrase (“Cocaine is a hell of a drug”).
Def Comedy Poetry Jam (featuring Mos Def)
The rapper now known as Yasiin Bey hosts a hybrid of the Russell Simmons HBO showcases. The sketch was included on Chappelle’s episode of creative failures, but it did give the world Mos Def in a cape yelling, “Are you ready for some poetry, mother[EXPLETIVES]?”
Kneehigh Park (featuring Q-Tip and the voice of Snoop Dogg)
Long Beach and Queens combine with kids and puppets in a sketch that makes “Avenue Q” look like “Howdy Doody.” Heroin and puppet genitals, together at last.
If you go: Dave Chappelle is at Radio City Music Hall Wednesday though June 26, 8 p.m. 1260 Sixth Ave., 212-307-7171, sold out