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Prince and Amy Winehouse’s Orbits Briefly Line Up for ‘Love Is a Losing Game’: 365 Prince Songs in a Year

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To celebrate the incredibly prolific, influential and diverse body of work left behind by Prince, we will be exploring a different song of his each day for an entire year with the series 365 Prince Songs in a Year.

Despite the perception of a man holed up in Paisley Park bringing his singular vision to fruition, the reality is that, throughout his career, Prince kept his eyes and ears open to new artists. His cover of Amy Winehouse‘s “Love Is a Losing Game” is proof.

On July 24, 2011, less than 24 hours after Winehouse’s death, Prince protege and band member Andy Allo began streaming an acoustic cover of the track, which is believed to have been recorded the previous day. Shortly thereafter, they offered it as a free download.

But Prince’s history with “Love Is a Losing Game” goes back farther than that. Originally released on Winehouse’s breakthrough 2006 album Back to Black, “Love is a Losing Game” reached No. 33 as a U.K. single in 2007. Prince performed it that April with his background singer Shelby J. on lead vocals, according to Prince Vault.

A week later, he said at a press conference in London that he was a big fan of hers and would “absolutely” invite Winehouse to perform it with him during his upcoming shows in the city. Of course, Winehouse was beyond thrilled by the indirect invitation. “I hope I can do [the gigs] though,” she told MTV News. “I’ll drop everything to do that. Stuff like that doesn’t make me go, ‘Oh, I must be the nuts.’ Stuff like that makes me want to do this tomorrow, and the night after, and the night after. Now I want to find out how solid that is. I’d do it with bells on. All day long.”

In late September, she joined Prince to perform the song at an aftershow in London. When they finished and Winehouse left the stage, Prince told the crowd “I got tears… I’m gonna have to get my shades on.”

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The two apparently spoke of working on new music together, and Prince invited her to Paisley Park, but it never happened. On July 23, 2011, Winehouse died of alcohol poisoning at the age of 27.

Allo, with Prince on guitar, released another acoustic version of the song on 2015’s Oui Can Luv, an album of mostly cover songs that was only available for 12 hours via the streaming service Tidal. Prince is presumed to have produced the recording.

When asked about losing fellow musicians, like Michael Jackson, specifically, in a Rolling Stone interview that went unpublished until after Prince’s death, Prince said, “I don’t want to talk about it, I’m too close to it,” but then went on to say, “He is just one of many who have gone through that door – Amy Winehouse and folks. We’re all connected, right, we’re all brothers and sisters, and the minute we lock that in, we wouldn’t let anybody in our family fall.”

Prince Albums Ranked in Order of Awesomeness

Next: 'Nothing Compares 2 U' Takes a Long, Strange Road to Immortality

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