When Prince held a press conference on 8 May 2007 to announce his record-breaking 21-night residency at London’s O2 arena, he mentioned that he’d taken to performing Amy Winehouse’s Love Is a Losing Game in his live set.
The emotive song appeared on Winehouse’s career-defining Back to Black album, which had been released the previous year, and released as its fifth single. She would have celebrated her 41st birthday on 14 September.
“I love the song,” Prince said of Love Is a Losing game, adding that he hoped that Winehouse would be able to make it along to one of the shows. Would he invite the star on stage to perform the song with him, though? “Absolutely,” he replied.
As luck would have it, Winehouse happened to be being interviewed by MTV on that very same day. And, inevitably, she was asked to respond to Prince’s offer.
Watching the footage back, it’s clear that this is the first she’s heard of it, and her initial reaction is of genuine disbelief. “I’m going to Minneapolis - see you later,” she jokes, clearly on board with the idea. “I hope I can do it, though - I’ll drop everything to do that,” she goes on to say.
Ultimately, Winehouse and Prince never did share the stage in the main O2 arena, but that isn’t where the story ends. Prince was known for his legendary aftershow gigs - some of which went on for longer than the shows that preceded them - and during his O2 run, he turned the neighbouring IndigO2 venue, which sits in the same complex, into his ‘3121 club’ so that he had a ready-made place to perform whenever he wanted to.
And so it was that, on 22 September 2007, the highly anticipated Winehouse/Prince duet did indeed happen, as grainy phone footage proves. Typically, Prince twisted Love Is a Losing Game’s arrangement slightly and allowed himself a guitar solo or two, but Amy definitely had her moment.
“I got tears - I’m gonna have to get my shades on,” said Prince after the performance, which clearly meant a lot to both artists.
He would return to the song in the hours after Winehouse’s death, on 23 July 2011, when he accompanied then protege Andy Allo on acoustic guitar as she sang it. The apparently one-take recording was originally streamed on Allo’s Facebook page.
Of course, Prince’s story would end in equally sad circumstances just a few years later, but while both he and Winehouse died tragically young, at least we can remember what they gave us when we had them.
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