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Dave Chappelle Canvassing For Andrew Yang

Source: Sean Rayford / Getty

15 years ago, Dave Chappelle completely shocked fans and colleagues alike when he walked away from his insanely popular  series Chappelle’s Show at its peak. All these years later, Dave told Gayle King that he decided to leave because “it just didn’t feel right” and despite all of his professional success, he wasn’t content emotionally.

Since the show was so popular, the move left a lot of people confused, at the time–especially since Chappelle reportedly rejected Comedy Central’s $50 million offer to complete a third and fourth season. Despite so many wondering what Chappelle was thinking, though there was one person who didn’t question Chappelle’s choice: Prince.

Within the liner notes for his upcoming Sign O’ the Times super deluxe edition, Dave reflected on Prince’s legacy and his reaction to the comedian’s decision to take a long break from Hollywood.

“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 said, according to reports from Vulture. “He was the only one I knew who had already done it … The mere sight of Prince reminded me that I’m not the last sane man on earth, and I’m not crazy.”

After that is when Dave hinted at Prince’s career-long battle with the music industry along with his relentless efforts to protect his art. In the 1990s, during his lawsuit against Warner Bros, Prince caused quite the ruckus when he performed at Wembley Arena with the word “slave” written across his face.

“He was the first person I knew who didn’t question my choices,” the comedian went on to say. “In fact, he didn’t even ask me about them. 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. Or, as he would say, ‘U gotta B free.'”



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