When Dave Chappelle was facing a huge life change in 2006, it was the wise words of his friend Prince that convinced the comedian he wasn't crazy.

The comic had decided to quit Chappelle’s Show after two complete seasons, reporting that its success was ruining his life and causing him stress. The conditions under which he left the production, which struggled on without him for several episodes, left his future career in doubt – but he felt he had no choice.

“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,” he said in a new interview featured in the liner notes of the Sign O’ the Times box set (via Vulture). Chappelle referred to one of his own sayings, that “the last sane man on earth is going to think he’s crazy,” before adding, “[Prince] was the only one I knew who had already done it. In the loneliest corners of that experience, there was always a sign… that he had been there and lived to tell about it.”

He continued: “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. Or, as he would say, ‘U gotta B free.’”

Chappelle also recalled the first time he’d heard the single “Sign O’ the Times” on a radio show presented by veteran host Casey Kasem. “I remember being struck by the way Kasem introduced the song,” the comedian said. “He actually read the lyrics before he played the record. That really impressed me. When would you ever hear a DJ read lyrics on a Top 40 countdown? The words were profound.”


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