"It's complicated" doesn't even begin to describe it
For example, someone started a Change.org petition decrying the choice, and news of the outcry apparently reached Billboard executive producer Mark Bracco, who defended the decision to have Madonna perform on Tuesday to the Associated Press.
Madonna and Prince had something of a tangled relationship, to put it mildly: Consensus seems to be that they dated in the mid-’80s. They collaborated in 1989 for “Love Song,” from Madonna’s album Like a Prayer. At some point, their relationship soured, to the point where Rolling Stone was making reference to a “decades-long” feud ending in 2011 and recalling incidents where Madonna referred to Prince as a “little troll.”
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But combing back through mentions of the pair, contradictory accounts emerge. In May 1985, PEOPLE wrote that they “weren’t, aren’t [and] never considered” having an affair, before noting that Madonna went to greet Prince with the announcement, “Time to go meet the midget.”
In the same interview, she vented: “He usually wants to be treated the exact opposite of the way he is dressed. His outfits say touch me, lick me, love me, lust me, but then he pretends he’s wearing a monk’s outfit. He needs to step back, look at his clothing and laugh at it.”
If that sounds a tad like an ex talking, it’s probably because that’s what Madonna was at the time. J. Randy Taraborrelli’s book Madonna: An Intimate Biography claims that Madonna and Prince met backstage at the American Music Awards in January 1985.
Per Tarraborelli, their first date was a Prince concert at the Forum; the diminutive singer apparently had to literally fight Madonna off while they rode to the show so he could conserve his energy for the show. “I heard she was pretty aggressive,” Prince’s friend T.L. Ross told the biographer. “She was strong. He told me that she had the strength of 10 women.” (Which, frankly, is hilarious, and probably true.)
The couple dated for the next two months, before Prince allegedly asked her to make things official. Things went south pretty quickly after Madonna – who presumably didn’t want to be tied down – declined his offer of further commitment.
Ross’s account differs slightly: “Prince is way too cosmic for Madonna. For him, making love is a spiritual experience. For her – at least at that time – making love was just a physical expression. While he wanted to savor every second of the experience, she was into multiple orgasms. After two months, he cut her loose.”
“After he stopped acting interested in her, that’s when the phone calls started. Madonna pestered him for weeks. He said later that she screamed at him, ‘How dare you dump me. Don’t you know who I am?’ She was definitely not used to getting dumped.”
All that said, the pair at least got around to being semi-friendly exes. Melinda Cooper, who was Madonna’s manager Freddy DeMann’s assistant, recalled that when Sean Penn was dating Madonna, he punched a hole in her wall after discovering that she’d dated Prince. The Material Girl then phoned Prince and told him to come fix the hole, “because you’re responsible for it, after all,” at which point Prince apparently showed up, plaster in hand, and dutifully repaired the wall. (This, too, is hilarious, and it’s surprising to me that it’s not a better-known piece of Prince lore. Plastering is not an inconceivable skill for Prince to have mastered; growing up in Minneapolis, he almost certainly had to handle plastering duties at some point.)
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Whether “Love Song” dates back to the pair’s relationship – they may have dabbled in writing together while dating – is unclear. But Prince also played guitar on “Act of Contrition” and “Keep It Together” from Like a Prayer, and reportedly offered her his song “By Alien Means,” according to Matt Thorne in Prince: The Man and His Music. Around this time, he also expressed interest in having her play the love interest in Graffiti Bridge, the 1990 pseudo-sequel to Purple Rain, a role she turned down
Whether from friendly competition as their careers progressed or not, the Madonna/Prince relationship altered slightly in the 1990s. In an interview with the Los Angeles Times in October 1994, Madge relayed the following story: “I was having dinner with Prince and he was just sipping tea, very daintily. I was stuffing food down my face and I was like, ‘Aren’t you going to eat?’ I have this theory about people who don’t eat. They annoy me.”
In that same interview, pressed on her relationship with Prince (and also Michael Jackson), Madonna was extremely candid. “I could never say that either of them were friends,” she said. “I’ve spent a great deal of time with both of them, and they have these manners and they’re just so careful about what they eat, and what they say. But it’s never too late to start being a human being.”
Through the ’90s, as Prince became embroiled in his battle with Warner, Madonna’s name came up again, at least in rumor. Alan Leeds – who was Prince’s former tour manager, president of Paisley Park Records and “was arguably as close to Prince as any other person” for a decade of the artist’s career, according to Rolling Stone – believes that some of Prince’s beef with Warner was related to Madonna.
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“His contract was coming up for renewal, and both Madonna and Janet Jackson had had contract renewals that had gained headlines,” Leeds told Thorne, “and he wanted a deal that would trump the Madonna deal.” (Liz Jones claims – in Slave to the Rhythm – that Madonna reached out to Prince after his struggles with Warner and suggested a merger between her label, Maverick, and his own, NPG Records, formed after Warner shut down Paisley Park Records in 1993.)
Information about the pair’s relationship seems to dry up as Prince went through his “Artist Formerly Known As” phase and Madonna’s career went into its nth reinvention, but there was a warming-up period at some point. At least, Prince felt comfortable enough with their relationship to joke that “I got more hits than Madonna’s got kids” during a 2007 concert in London.
Eight years later, in 2015, it emerged that Prince invited Madonna and her crew back to Paisley Park after her Minneapolis show for an after-party and private concert that culminated with him serenading her as she sat on the edge of the stage. Six songs into the set, the pair had a whispered exchange, and then Madonna left. Prince continued to play. It probably wasn’t their last interaction, but it was a fitting one: Prince playing for one of his peers, decades after they’d ruled the world and maybe, probably, had gotten together in the middle of it.