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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.

Miles Davis and Prince dance onstage at Paisley Park: Still from Sign o’ the Times: New Year’s Eve 1987 (photo: Courtesy of Warner Records)
Miles Davis and Prince onstage at Paisley Park in a still from Sign o’ the Times: New Year’s Eve 1987 (photo: courtesy of Warner Records)


Such control was put to the test at the New Year’s Eve 1987 show documented in the Sign o’ the Times box. As Leeds notes, it was “the only time Miles and Prince were together in real time making music.” The occasion was a private party celebrating the opening of Prince’s Paisley Park studio complex in suburban Chanhassen, Minnesota.

“Miles was invited, and asked, if he wished, to bring his horn and come join us on stage to jam,” Blistan says. “It was great. Miles even asked me to test his wrap-around [monitoring] equipment during the soundcheck.”

Blistan recalls Miles strolling onto the Paisley Park stage as the band launched into “It’s Gonna Be a Beautiful Night,” warmly greeted by Prince. “Miles is playing and, always, during any set, we have cues—three or four—that Prince could give us by showing a certain hand gesture. If he threw his hand up in a particular manner, there was a riff that the band knew to insert at that point. Could be a jam. Could be a funk song or a ballad. When we saw the hand, we knew immediately on the next phrase what we were going to do.”

Leeds takes the next part of the story: “Miles is playing. Prince is facing us and, in the middle of that, he throws up his hands for one of those cues. But nobody in the band paid Prince any attention … at all. We were all just looking at Miles. Nobody hit the cue. And Prince got pissed. He threw his hand up expecting reaction from the band—nothing. He looked at us and yelled, ‘Hey,’ as if to say, ‘I’m over here. I’m still running the show.’ Then he gave us another cue, and we were on top of that.”

What Blistan and Leeds regret most about that evening is that they had wanted to show their love and respect to Miles during “It’s Gonna Be a Beautiful Night” by playing a riff they adored, a blip at the top of side two of Davis’ Agharta that the Pittsburgh pals had tossed into jams since their club days. “I was just waiting to throw that riff in, elbow Matt as a signal to hit it—just to see what the look on Miles’ face might be,” Leeds says. “For whatever reason, though, I hesitated too long … the moment passed. I will always kick myself for that.”

“Who knows?” Blistan says. “Miles may have turned around and given us a dirty look, like ‘C’mon, playing something I played 30 years ago?’ We’ll never know.”

The realization that Miles’ presence could loosen Prince’s hold over his band, even if only for a moment, seems to have tempered his interest in further collaboration. Leeds readily admits that Prince was intimidated. 

“After the New Year’s Eve show, Miles was still very interested in wanting Prince to produce him, one on one, really hands-on, to see what Prince could do,” he recalls. “Prince was scared to death by that notion. In these words, he said, ‘I don’t know how to tell Miles Davis to play music.’ I explained that Miles wasn’t looking for that, he just wanted some of what Prince had, something that might lead him to play something different, respond differently.”

Eventually, Prince sent the jazz legend several Madhouse tracks, originally intended for that side project’s never-completed third album (read more about that here). Leeds also remembers helping Prince put together a version of his “Nothing Compares 2 U” for Davis—think of what Miles could’ve done with that tune—but he’s uncertain what happened to it. Maybe these are the recordings Vince Wilburn Jr., Davis’ nephew and executor of his estate, was alluding to when he said in a recent interview with the U.K. music magazine Mojo, “[T]here should be more [Miles/Prince] music … If they [Prince’s estate] want to revisit anything, we’re all ears. We’re still hoping. You can quote me on that.” Then again, maybe not.

Miller regrets that Prince and Miles never got it together, but acknowledges that the only true road to positive results for the duo would have been full immersion and deep commitment. “The most obvious way would have been for Prince to do Prince, and have Miles join in fully,” he says. “I don’t know about Prince, but Miles was flexible. I would have loved to have had them spend real time together. Hear what it would have sounded like if Miles’ sound was truly in Prince’s ear. For Prince to write for that voice—because that voice was so strong, so beautiful—that would have been amazing.” 

The Story of Prince and Madhouse