Prince Loved When He Was Portrayed by Dave Chappelle

Editor’s note: Dave Chapelle performed a four-hour 2 a.m. set Friday at San Francisco’s Chapel venue, telling the audience: “I almost thought about not coming tonight, but my band was like, ‘Yo, Prince would definitely not condone that.’ And now there is no place I’d rather be.” The San Francisco Chronicle reports that his backing band performed renditions of “Kiss” and “Nothing Compares 2 U” on a purple-lit stage as Chapelle said, “This is black 9/11. It’s so much better that we grieve together.”

One near-universally beloved Chappelle’s Show sketch features Dave playing Prince. It turns out that the legendary artist was also a huge fan.

Chappelle’s Show cast member Donnell Rawlings told The Hollywood Reporter he will never forget making the sketch and he hopes it will help fans somewhat overcome their sadness.

“He thought it was hilarious,” Rawlings says of Prince’s reaction. “And I think [Chappelle and Prince] really built a friendship after that sketch.”

The sketch, “Charlie Murphy’s True Hollywood Stories - Prince,” first premiered Feb. 18, 2004, and featured Chappelle playing the music icon while Murphy reminisced about their actual crazy basketball game one night in the mid-‘80s. Rawlings played Murphy’s buddy in the sketch.

“Dave wanted Prince to be in the sketch, and he asked him about it and Prince told Dave, 'Yeah, nah,’” Rawlings recalls with a chuckle. “And that’s true to Prince’s fashion with dialogue. You’ll probably never hear of Prince talking more than three sentences.”

Rawlings contends that the sketch became so well-known and beloved, people go Chappelle and Prince confused.

“Some people think Dave Chappelle is Prince. I’m pretty sure someone had to put out some disclaimer saying 'Dave Chappelle is not dead. Prince died,’” Rawlings says laughing. “Prince is much larger than a sketch, but just showing what Chappelle’s Show did for the art form, when you mention Prince and his music, there is no way to get around that groundbreaking sketch.

Rawlings remembers the first time he saw Chappelle dressed like Prince.


(Prince’s 2013 single “Breakfast Can Wait” featured Chappelle dressed as Prince as its cover art)

"It was so funny … it was a 6-foot Prince,” Rawlings says in hysterics. “Just to see him walk in, in that purple outfit, with the blouse and wig – the entire set just lost their s—.”

Rawlings met Prince once before, kind of, he says. It’s a moment he’ll never forget. “There’s certain people, when you’re in their presence, you just shut up.”

“Prince was at the Boston comedy club in the village, and I wanted to talk to him,” Rawlings remembers. “There was just something about him. There wasn’t a spotlight or anything, but it just looked like he was perfectly lit and his face was glowing. And he stared and I stared … I’ve never been attracted to a guy in a blouse before, but for some reason that day, Prince looked attractive to me,” he says laughing. “And I was like 'Donnell, shake it off. Don’t get caught up in the rapture of his eyes.’ And I think that’s why Prince wore shades so often because he knew if he made eye contact with you, there could be some questions.”

Chappelle and Prince are very much alike, Rawlings says.

“They both are original artists and they weren’t going to comprise to what Hollywood thought the norm was,” he says. “And those are they type of people you remember for the rest of your life.”

Rawlings says he is hurting like most of the globe with the news of Prince’s passing, but he hopes the Chappelle’s Show sketch will ease some fans’ pain.

“The world we live in now, people come and go … and I think it’s awesome that the millennials and younger people may have gotten reintroduced to Prince through a comedy sketch.”

This article originally appeared in The Hollywood Reporter.