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The Ballad of Miles Davis and Prince

In the mid-1980s, two creative titans met, one from the jazz world and one from the pop world. A newly expanded, multi-disc exploration of Prince’s ’87 masterpiece Sign o’ the Times partly reveals what happened—and what could have been—between them.

Prince (photo: Jeff Katz/Courtesy of the Prince Estate)
Prince (photo: Jeff Katz/Courtesy of the Prince Estate)


The saga of Prince and Miles could not end with one bum song in 1986; that’s what makes the legend flourish. The two kept in contact, hung out and weaved around each other, perhaps fearful of commitment. Leeds and Blistan both remember March of 1987, when Davis came to Minneapolis for a concert at the Orpheum Theatre.

“Miles came out to Prince’s warehouse to hang a day before his gig—this would have been Matt’s and my opportunity to chill with him,” Leeds recalls. “I was doing something with Prince. Matt was just sitting when Miles took the barstool next to Matt and sat down. I’m looking at Matt—one of my dearest, oldest friends—sitting next to his absolute hero. I always wished I had a photo of that.” 

Blistan laughs as he imitates Davis’ introduction (a raspy “I’m Miles”) and remembers happily that the two talked embouchure and equipment while waiting for Prince and Miles to meet. “We had a good discussion about the stuff Prince had on stage, like our Fairlight sampling keyboards. They were $30,000 each. Prince had two. Miles was impressed.”

Later that same night, Miles, percussionist Sheila E., Prince’s jazz-pianist father John L. Nelson, and Leeds all had dinner with Prince at his house, an experience the saxophonist calls “the most fascinating several hours of my life. Miles was on, performing. Is it really so difficult for music writers to get that 90% of what he said, he said for effect? He wanted to get a rise out of people, saying the most ridiculous, obscene, absurd shit just to watch people react. It’s how he enjoyed himself.” 

Eventually the subject turned to other trumpeters. “I knew there were musicians that Miles loved to put down,” Leeds says, so he threw out Lester Bowie’s name, figuring Miles would have little time for the Art Ensemble of Chicago mainstay. Instead, he got this rejoinder: “Eric, why the fuck wouldn’t I love Lester Bowie?”

“Wow, cool,” Leeds says. “I got him to admit somebody else was a badass trumpet player with his own identity. No way in the world would he have said that about Freddie Hubbard, he would never give it up to him. Funny thing too, about Miles and Prince—they would never truly give it up to each other. They both loved and identified with each other, yet you could see the wheels turning. Prince had nothing but adoration for Miles. Miles was the template for everything Prince aspired to as an artist. But in Prince’s eyes, Miles was the old man: ‘I’m the new you.’ And Miles, [though he] respects the hell out of what Prince does, is thinking, ‘You may be the new version of me, but without me there is no you.’ Everything they said to each other, how they interacted, was nothing but a dance. It was hilarious to watch two superegos dance around each other. Neither one of them was going to be the first one to give it up.”

Mention this summation to Miller, and he’s very clear. “Working with Miles as I did, there was never a question of who would be top dog: Miles was Miles,” he laughs. “He’d been Miles since 1945. It might have, however, been uncomfortable for Prince, who wasn’t in any situation where he wasn’t Prince. He was always in control of his surroundings.”