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

Bringing together musical geniuses with huge egos—no matter what respect or affection exists between them—can be more difficult than uniting warring nations or battling spouses. So it was with the brief dance between Prince and Miles Davis.

In the first half of the 1980s, Prince established himself as a wunderkind-auteur known for rolling cosmopolitan R&B, funk, psychedelic rock, and new wave into one sweetly soulful yet edgy pop mélange. In that same period Davis, jazz’s eclectic, ever-changing trumpet god, re-emerged from a five-year retirement and left his longtime label Columbia for Warner Bros., Prince’s industry home since 1977. That each loved the other’s work is no secret; that they actively sought collaboration is the stuff of legend.

Now, more than three decades after the twosome sort of connected, what little fruit was yielded from that pairing (perhaps?) is part of an epic reworking of Prince’s 1987 chart-topping double album Sign o’ the Times. Its new Super Deluxe edition contains 63 previously unreleased tracks from Prince’s storied vault, as well as a two-hour-plus DVD featuring his only onstage collaboration with Davis, during a New Year’s Eve 1987 benefit concert at his then-new Paisley Park studio in Minnesota. Within that same package—eight CDs or 13 LPs—is “Can I Play With U?,” a track composed and played by Prince for inclusion on Miles’ first Warners album, 1986’s Tutu, but left on the cutting-room floor.

This exciting archival development can’t help but prompt a question, necessitated by 30 years of fevered rumor: Is Davis’ slithery trumpet blare across a lengthy “It’s Gonna Be a Beautiful Night/Auld Lang Syne” live medley and one unused, good-not-great pop track really everything Miles and Prince did together?

Providing an answer, and further background on the Miles/Prince pairing, are three players who were there: Marcus Miller, the bassist, composer, and co-producer behind much of Davis’ 1980s output; Matthew Blistan, a.k.a. Atlanta Bliss, Prince’s trumpeter from 1985 to 1991; and Eric Leeds, Prince’s saxophonist and horn arranger from the tail end of the 1984-85 Purple Rain tour through to 1992’s The Love Symbol Album. Leeds also teamed with Prince for several forays into instrumental jazz-funk under the name Madhouse. That several unused Madhouse tracks were attractive to Miles—so much so that he recorded them toward the end of his life—just adds to the royal duo’s list of could-have-beens.