Despite being among the best-remembered segments from Chappelle’s Show, “Charlie Murphy’s True Hollywood Stories” was only featured twice during the series’ run on Comedy Central. The first sketch, of course, covered Murphy’s encounters with infamous “Super Freak” hitmaker Rick James. They followed that up a week later with an equally memorable sketch in which pop icon Prince and his band, The Revolution, mopped the floor with Murphy and his crew in a game of basketball. Check it out below.
According to Donnell Rawlings, who also appeared in the sketch, Prince took Chappelle’s over-the-top portrayal of him in stride. “He thought it was hilarious,” Rawlings told The Hollywood Reporter of the Purple One’s initial reaction. “And I think [Chappelle and Prince] really built a friendship after that sketch.” Furthermore, Rawlings revealed, Chappelle even reached out to Prince prior to filming the episode. “Dave wanted Prince to be in the sketch,” Rawlings remembered, “and he asked him about it, and Prince told Dave, ‘Yeah, nah.’”
Although he had a good sense of humor about the whole thing, Prince got some playful revenge on Chappelle nine years later when he used a picture of the comedian imitating him on the cover of his 2013 single “Breakfast Can Wait.” When Jimmy Fallon showed the photo during an interview with Chappelle back in 2014, Chappelle reacted by saying, “That’s a Prince judo move right there.” Chappelle explained that the songwriter never bothered to clear the image with him. “You make fun of Prince in a sketch, and he’ll just use you in his album cover,” he joked. “What am I gonna do, sue him for using a picture of me dressed up like him? It’s impossible…that’s checkmate right there.”
Years later, Chappelle credited Prince with being the person who convinced him he wasn’t crazy after he walked away from his popular Comedy Central series in 2006 after signing a $50 millon deal for two additional seasons. “When I left Chappelle’s Show, not only was Prince the only person I could relate to, he was one of the few people who truly cared about what was happening in my life,” Chappelle recalled in the liner notes for the 2020 Prince box set Sign O’ the Times. “The mere sight of Prince reminded me that I’m not the last sane man on earth, and I’m not crazy. He was the first person I knew who didn’t question my choices. He just told me, ‘Whatever it is, you’re right.’ He helped me understand that it might not be over and that there might be another side to it…and whether or not there is or isn’t, at least you’re free.”
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