How Dave Chappelle 'Knew Kanye Was Going to Be a Star' - Rolling Stone
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How Dave Chappelle ‘Knew Kanye Was Going to Be a Star’

Comedian talks about his first encounter with the rapper and dishes on Prince with Jimmy Fallon

Dave Chappelle continued making the late-night TV rounds on Friday, appearing on The Tonight Show to talk to Jimmy Fallon about his upcoming string of dates at Radio City Music Hall. The comedian announced that Nas will be joining the show on June 23rd, and reminisced about how he came to work with the Roots after being mistaken for a lost member of the group in Portland, Maine.

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Chappelle also talked about his first encounter with Kanye West, whom Chappelle booked to perform on his Comedy Central sketch show before the rapper was famous. Chappelle said that it was clear even then that West was destined for greatness. “It was Muhammad Ali in Olympic Village. He just knew he was gonna get the gold,” Chappelle said. 

According to Chappelle, West received a call while he was backstage with the show’s crew watching unaired sketches during editing. West reportedly told the caller that he was unavailable because “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.”

“This is when everybody knew Kanye was going to be a star,” Chappelle said.

Chappelle also talked about Prince using an image from The Chappelle Show as the artwork for his single “Breakfast Can Wait.” “That’s a Prince Judo move, right there, isn’t it?” he said. “You make fun of Prince in a sketch and he’ll just use you in his album cover. What am I gonna do, sue him for using a picture of me dressed up like him? That’s check mate right there.” 


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