He spoke highly of the late icon both in his autobiography (“His shit was the most exciting music I was hearing in 1982,” he wrote, “so I decided to keep an eye on him”) and in interviews like the widely-circulated clip below, in which he compares Prince to everyone from James Brown to Charlie Chaplin.
But it was more than just a mutual admiration society — the pair met (per Prince’s former tour manager, Alan Leeds, via a 1985 chance encounter at LAX), and were in the process of working together when Miles passed in 1991 (some of his last performances included Prince covers and compositions he’d done specifically for Davis). Below is the unreleased record “Can I Play With U?,” which Prince had written for Davis’ 1986 album Tutu and pulled after he didn’t like the final product.
“What Prince really related to about Miles was his character,” said the Purple One’s frequent saxophonist Eric Leeds, “his legacy, his mystique and everything that Miles represented as a personality. Prince saw in Miles so much of what he thought of himself – the person that goes against the grain, that’s opinionated, that doesn’t allow himself to be controlled by any aspect of the industry for his own artistic vision. And that’s very much what Miles saw in Prince. He saw a young version of himself.”
Watch Davis’ 1991 performance of “Penetration,” one of the songs Prince wrote for him, below.