How Dave Chappelle Got “Checkmated” By Prince

Written by Greg Moskovitch on 16th June, 2014

How Dave Chappelle Got “Checkmated” By Prince

Dave Chappelle appeared on The Tonight Show Starring Jimmy Fallon recently, during which he discussed meeting Kanye West and the show’s house band The Roots. Host Fallon also questioned the comedian about being featured on the artwork for Prince‘s 2013 single Breakfast Can Wait.

Chappelle first recounted how he met The Roots after he was mistaken for a member of the band at a mall and later attended their show. “I was in Portland, Maine and I was walking in a mall and [The Roots] had been there an hour earlier so I guess they thought I was like a lost Root. A lady comes up and asks for an autograph and I’m signing it and she’s like, ‘I love The Roots.’ I’m like, ‘The Roots?’”

Addressing Prince’s use of an image of Chappelle from his show’s iconic “Prince sketch,” he said, “That’s a Prince judo move. Make fun of Prince in a sketch and he’ll just use you for an album cover. What am I gonna do? Sue him for using a picture of me dressed up as him? That’s checkmate.”

The comedian then shared memories of the first time he met West, which was on the day that Jay-Z‘s The Black Album was released. Chappelle recounted how he, West, Common, and Talib Kweli were listening to the album in a trailer and West demanded they rewind Jay-Z’s shout-out to him.

Later, when Chappelle was showing the rapper early cuts of upcoming sketches for his Comedy Central show, West answered a phone call by proclaiming, “I’m at the edit for the Chappelle’s Show watching sketches no one has seen before… because my life is dope and I do dope shit.”

Watch: Dave Chappelle Talks Prince and Kanye with Jimmy Fallon

(Image: The Tonight Show Starring Jimmy Fallon / YouTube)


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