The Only Time Prince & Miles Davis Jammed Together Onstage: Watch the New Year’s Eve, 1987 Concert

A too-pre­cious genre of inter­net meme depicts depart­ed pub­lic fig­ures who did not know each oth­er in life meet­ing in heav­en with hugs, high-fives, and winc­ing­ly earnest exchanges. These sen­ti­men­tal vignettes are almost too easy to par­o­dy, a kitschy ver­sion of the “what if” game, as in: what if two cre­ative genius­es could col­lab­o­rate in ways they nev­er did before they died?

What if John Lennon had formed a band with Eric Clap­ton—as Lennon him­self had once pro­posed? Or what if a Jimi Hendrix/Miles Davis col­lab­o­ra­tion had come off, as Hen­drix envi­sioned the year before his death? More than just fan­ta­sy base­ball, the exer­cise lets us spec­u­late about how musi­cians who influ­enced each oth­er might evolve if giv­en the chance to jam indef­i­nite­ly.

When it comes to Miles, there are few who haven’t been influ­enced by the jazz great, whether they know it or not. Prince Rogers Nel­son knew it well. The son of a jazz pianist, Prince grew up with Miles’ music. Although he “grav­i­tat­ed to the worlds of rock, pop, and R&B,” writes pianist Ron Dro­tos, Prince “seems to have seen jazz as a way to express him­self in a broad­er way than he could through more com­mer­cial styles alone.”

Prince was so inter­est­ed in explor­ing jazz—and Davis’ par­tic­u­lar form of jazz—in the 80s that he formed a band anony­mous­ly, called Mad­house (actu­al­ly just him and horn play­er Eric Leeds), and released two albums of fusion instru­men­tals. The influ­ence went both ways. “Miles con­sid­ered Prince to have the poten­tial to become anoth­er Duke Elling­ton and even mod­eled his own 1980s music part­ly on Prince’s style,” with 1986’s Tutu stand­ing out as an exam­ple. What if the two musi­cians had worked togeth­er? Can you imag­ine it?

They did not—to our knowl­edge, although Prince’s vault is vast—collaborate on an album, but they did cre­ate one stu­dio track togeth­er, “Can I Play With U?” And the two vir­tu­oso com­posers and musi­cians jammed togeth­er onstage, once, at Pais­ley Park, on New Year’s Eve, 1987. The con­cert was a ben­e­fit for the Min­neso­ta Coali­tion for the Home­less and the last time Prince per­formed the Sign O’ the Times stage show. At the tail end of the con­cert, Davis steps onstage for “an ice-cold appear­ance,” Okay­play­er notes. “As a com­pan­ion to the release of a deluxe edi­tion” of the album, “the late icon’s estate has relin­quished the full two-hour-plus set.”

Watch the con­cert at the top (trust me, don’t just skip ahead to see Davis at 1:43:50). Just above, you can see an hour­long “pre-show” taped with Maya Rudolph, “life­long Prince devo­tee,” Emmy-win­ning come­di­an, and daugh­ter of Min­nie Riper­ton. Oth­er guests include Prince’s long­time side­man and col­lab­o­ra­tor on his jazz project, Eric Leeds. “If you’re here, then you’re cool, like me,” Rudolph jokes, “and you know a lot about Prince.” Or maybe you don’t. Let Rudolph and her guests fill you in, and imag­ine Prince and Davis mak­ing celes­tial jazz-funk for­ev­er, between high-fives, in the Great Beyond.

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