"It's a hard thing to talk about. I looked up to him like everybody did. I didn’t know him that well, but the times that we hung out were fun and very memorable and often funny. He was very generous with his advice, and he was very generous with his access," Chappelle said of Prince.
"He fostered a community among artists. He used to have these parties where we would go over to his house, and there would be all these musicians that I admired, and they’d just do these jam sessions in the basement. Everybody at the party was playing something. I think when he died there was the icon dying, but then there was this pillar in the community of people dying."
Chappelle also talked about Bill Cosby, who was a major influence on his comedy; Cosby's legacy has been permanently marred by decades of allegations of sexual assaults from dozens of accusers.
"The Bill Cosby thing was tough for me. I'm not saying that to detract from his alleged victims at all. But he was a hero of mine," Chappelle said.
"So many bad things happened to our heroes: Muhammad Ali had Parkinson's; Richard Pryor had M.S.; Prince died too young. And Bill just looked like one of the guys who was going to get to the finish line and just die of old age. And this happened. Jesus Christ. It’s awful."
In the New York Times interview, Chappelle also talked about his now-classic SNL monologue in the first post-Election Day episode and why it's difficult for comedians to poke fun at Trump, even if the president seems like an easy target.
"[Trump's] so skewed, it's hard to find an angle that sounds fresh," Chappelle said. "If you talk about him, it’s almost like you're part of the chorus and not a soloist."
Chappelle will release his first two Netflix comedy specials, The Age of Spin and Deep in the Heart of Texas, on March 21st, with a third special featuring all-new material also planned for 2017.