Prince said “I got tears” after singing with Amy. Then he offered to send a plane. She never went.
After Amy Winehouse and Prince performed together at the O2 in 2007, Prince walked off stage and said four words. He said, “I got tears.” Then he invited her to fly to his home in Minnesota to record together. She never went. And four years later, the day after she died, he picked up a guitar. But to understand what that night at the O2 actually was and what it was supposed to become, you need to go back four months earlier to a press conference in London in May 2007, where Prince announced a residency that the music world was not quite prepared
for. Prince had booked the O2 Arena for 21 nights, not one night, not a weekend run, 21 consecutive nights at one of the largest indoor venues in Europe. An undertaking so audacious that the music industry had spent weeks discussing whether it was possible before discussing whether it was a good idea. He had announced it with the particular confidence of someone who had been doing impossible things for so long that the impossibility had stopped registering.
And in the press conference, almost as an aside, he had mentioned something else. He had been performing Amy Winehouse’s Love Is a Losing Game in his live set. He loved the song. He hoped she would come to one of the shows. Would he invite her on stage? Absolutely, he said.
He said it without hesitation, the way he said most things, with the directness of someone who had decided and was simply reporting the decision. Amy was being interviewed by MTV on that same day. When the journalist told her what Prince had said, she heard it for the first time on camera, in real time, with no preparation and no publicist and no carefully considered response waiting to be deployed.
Her face did exactly what faces do when someone receives genuinely unexpected news that is also genuinely wonderful. The disbelief came first, then something else, the specific joy of being recognized by someone whose recognition meant something. What she said next was not a managed response.
It was Amy Winehouse unguarded saying what she actually felt about music and why she made it. She said she would drop everything. She said stuff like this doesn’t make me think I’m the greatest, it makes me want to do this tomorrow and the night after and the night after. She said she wanted to find out how solid the offer was.
She said she would do it with bells on. The significance of that response lies not just in its spontaneity, but in what it revealed about Amy’s relationship to her own work. She was 23 years old and she had just won five Grammy Awards and Back to Black was one of the biggest selling albums in the world and what made her want to keep making music was not the awards or the chart positions or the critical acclaim.
It was the thought that Prince, a man who had been making music since she was a child, who had written Purple Rain and Kiss and When Doves Cry and Sign of the Times, who was one of the most technically accomplished musicians alive, had been performing her song in his live set because he loved it. That was the thing that made her want to do it tomorrow and the night after and the night after.
What Prince had been doing with Love Is a Losing Game before that September night was itself significant. He had been performing it in his live set for months, covering it with his backing singer Shelby J, taking a song that was already being described as one of the greatest ballads of the decade and making it part of his own live show.
This was not a casual gesture. Prince was meticulous about what he performed. He did not cover songs because they were popular or because covering them would generate goodwill. He covered songs because he heard something in them that he needed to inhabit, that said something he wanted to say, that belonged in the same room as the music he had been making for 30 years.
Love Is a Losing Game said something that Prince understood at the cellular level. The song was about loving someone who was destroying you and knowing it and choosing to keep loving them anyway. About the specific and devastating logic of a feeling that does not respond to reason. Prince had written about that experience himself in different registers and different vocabularies throughout his entire career.
When he heard Amy’s version, spare orchestral, written in the key of real grief rather than performed grief, he heard someone saying the same thing he had always been trying to say and saying it as well as he had ever heard it said. Prince’s 21-night residency at the O2 ran through the summer and into the autumn of 2007.
>> [snorts] >> Amy attended the final night, September 22nd, and what happened that evening became one of the most discussed moments of both their careers. She appeared at the after show, an event held in a a space attached to the main arena, and Prince brought her on stage to perform Love is a Losing Game together.
The footage that exists from that night is grainy and imperfect, shot on mobile phones by people in the audience who understood that something was happening they needed to document. It shows two performers, one in his late 40s, one in her late 20s, occupying the same small stage and singing a song that one of them wrote and both of them understood completely.
Prince had modified the arrangement slightly, as he always did with songs he covered, adding a guitar solo, reshaping the rhythm underneath it, making it his without removing what made it Amy’s. And Amy sang, and the voice was the voice, and the grainy footage was somehow entirely sufficient to capture what was happening.
When it was over, Prince walked off stage and said four words, “I got tears.” He said it simply and without elaboration, which was the only way to say it. He had been in the music industry for 30 years. He had performed with James Brown and Miles Davis and Joni Mitchell. He had played guitar at a Prince tribute concert for Prince.
He was not someone who was easily moved. He said, “I got tears.” And put his sunglasses on and meant every word of it. Afterward, in the dressing room, something happened that Tyler James, Amy’s oldest friend who had been there that night, wrote about years later in his memoir My Amy. Blake Fielder-Civil had joined them backstage.
Prince’s dressing room had cash on the table, not unusual in the context of a touring operation, just money that had been left out without anyone paying particular attention. Blake was in a bad state. He went into Prince’s bathroom, and when they left, the money was gone. Amy called Prince the next day and apologized.
She promised to return the money, but Prince was direct with her about something. He told her the money was no longer the point. What had happened in that dressing room, what he had witnessed, what it meant about the situation Amy was living inside, that was the point. He was worried about her. He told his videographer, Phil Griffin, that he wanted to help.
He asked if there was anything that could be done to get her away from Blake. He said he would send a plane. The offer was real. Prince was a man of considerable resources and considerable conviction, and when he said he would send a plane, he meant that he would send a plane. He had invited Amy to Paisley Park, his home and studio complex in Chanhassen, Minnesota, to record together.
He had made one condition, reported by the people around them, Blake should not come. The trip was a professional visit, a creative collaboration between two artists who had just performed together, and who both understood what the other was capable of. It did not need to be anything else. Amy said yes.
She was delighted, the people around her said, “You do not turn down Prince.” The invitation to Paisley Park, to the place where he had made Purple Rain, where he recorded everything, where the music lived when it was not on a stage, was not the kind of thing that a person who loved music the way Amy loved music could say no to. To understand what Paisley Park invitation actually represented, you need to understand what Paisley Park was.
It was not simply a recording studio. It was the physical manifestation of Prince’s creative autonomy, the place he had built in Chanhassen, Minnesota, in 1987, so that he would never again need to be somewhere else to make music. It had recording studios and rehearsal spaces and a sound stage and living quarters and every piece of equipment he had ever needed or imagined needing.
It was where Purple Rain was mixed. It was where Sign of the Times was made. It was where he went when he needed to be completely inside the music without the interruption of the world outside. To be invited to Paisley Park was to be invited into the innermost circle of Prince’s creative life. It was not a professional visit to a commercial studio.
It was an act of genuine trust from a man who was famously private about his process, famously protective of his space, famously uninterested in collaboration that was not born from authentic mutual recognition. He had invited Amy because he had heard her sing and understood what she was and believed that what they could make together was worth the vulnerability of sharing that space.
The trip never happened. The reasons it never happened are the reasons that most things in Amy’s life in that period did not happen. The accumulating weight of everything that was going wrong, the addiction, the deteriorating health, the chaos that Blake’s presence in her life generated and that she could not bring herself to leave.
The Paisley Park visit stayed in the category of things that were planned and then were not, things that were real until they were not, things that the people who loved Amy spent the years after her death cataloging with the specific grief of the almost. Prince did not forget. In the Rolling Stone interview that was conducted before his death but only published afterward, he was asked about losing fellow musicians.
He said he did not want to talk about it, that he was too close to it. And then, as if the not wanting to talk was itself insufficient to contain what he actually felt, he said this, He is just one of many who have gone through that door, Amy Winehouse and folks. We are all connected. We are all brothers and sisters, and the minute we lock that in, we would not let anybody in our family fall.
He had tried not to let her fall. He had offered a plane. He had made the call. He had extended the invitation in a form that was serious and concrete and genuine, and it had not been enough. Not because of any failure on his part or hers, but because the things that needed to align for that plane ride to happen had not aligned, and then time had run out.
On July 23rd, 2011, Amy Winehouse died. She was 27 years old. On July 24th, less than 24 hours later, Prince picked up a guitar. He sat with his protégé, Andy Allo, and they recorded Love Is a Losing Game. One take, acoustic, with Prince on guitar and Allo singing the melody. They offered it as a free download.
There was no press release, no statement, no explanation. The recording existed, and then it was available, and the people who heard it understood immediately what it was. A man who had cried on stage when he sang with its author, who had tried to send a plane to save her, who had named her among the family he had not been able to keep from falling, picking up his guitar the day after she died and playing her song back into the world.
He did not say why. He did not need to say why. The guitar said it. Prince died on April 21st, 2016. He was 57 years old. His cause of death was an accidental fentanyl overdose, the same general category of loss as Amy’s, the same story of an extraordinary talent destroyed by a substance, the same gap between what the person was capable of and what the ending looked like.
He joined the list that he himself had named, the ones who had gone through that door. There is a particular resonance in the fact that Bob Dylan in 2017 named Amy Winehouse the last real individualist in music because Prince was the other answer to that question, the one from the generation before Amy’s, the one who had been doing it since the late 1970s.
Two individualists from different eras and different musical traditions who had found each other briefly in 2007 and recognized something essential in each other. Prince had built Paisley Park so that nobody could tell him what to make. Amy had written Back to Black in 5 days because she had something to say and the only acceptable form for it was the most honest one.
They were doing the same thing from different directions. The collaboration they were planning was not the meeting of a legend and a fan. It was the meeting of two people who both, in their different ways and their different circumstances, had refused to be other than what they were. That was what the plane was for.
That was what Paisley Park was for and that was what the guitar was for the morning after she died. What they were to each other in the brief orbit of 2007 and the unrealized potential of Paisley Park and the guitar played the day after she died was something that neither of them fully articulated while both of them were alive.
Prince said he got tears. Amy said she would do it with bells on. That was the full extent of the public record of what they meant to each other. But the recording exists, the grainy footage from the O2 aftershow exists. The acoustic version of Love Is a Losing Game recorded in 24 hours of grief exists.
And in the space between those things, between the press conference in May and the guitar in July and the four years in between when the plane was offered and never taken, is the story of two extraordinary musicians who found each other briefly and incompletely and whose collaboration existed as a single performance on a London stage and a single acoustic guitar the morning after the world lost one of them.
The song was always a losing game. Prince knew it when he covered it. Amy knew it when she wrote it. And the day after she died, he sat down with a guitar and proved one more time that he had understood it completely.
