Artists performed “Love is a Losing Game”, by the British singer, in a much less grand environment than the occasion called for
The year was 2007 and Prince announced a season of 21 shows as a resident at the O2 Arena, in London. The commitments were part of its Earth Tourwhich promoted the album Planet Earth (2007). At the time, the big name of the moment was Amy Winehousewho had released his great success, the album Back to Black (2006).
Confirmation of the series of performances by the American artist in the British capital took place in May of that year, with a press conference by the star. Over there, Amy was one of the subjects — more specifically music “Love is a Losing Game”one of the hits from the artist’s album, released as a single at the end of 2007.
Second article of Music Radar, Prince He said he loved the song. Asked about a possible duet with Winehouse at one of the O2 Arena shows, he confirmed his intention.
In one of those magical coincidences in the music world, Amy gave an interview to MTV on the same day and was asked about the author’s statement of “Purple Rain”. From the Englishwoman’s reaction in the video below, you can see that the idea of singing with Prince he left Amy more than excited.
In the middle of the interview, she even jokes: “I’m going to Minneapolis (Prince’s hometown) – I’ll see you later”, while pretending to get up from her chair. Check it out (in English).
Prince and Amy Winehouse
In the end, Amy Winehouse did not participate in any of the shows Prince at the O2 Arena residence. Still, the duet happened.
The American was remembered for the gigantic “afters” concerts he organized after performances. Always in front of a select group of guests, he performed very different setlists with no end time.
For the 21-night sequence in London, a venue attached to the O2 Arena was set aside for this purpose and renamed 3121 Club. The building was available when Prince wanted to play — and it was on one of those nights that Amy Winehouse appeared and sang “Love is a Losing Game” with the idol.
Some changes were made to the arrangement, including guitar solos and other details. There is no official footage of the event, only audio recorded from the public. In the end, an emotional Prince declared: “I have tears (in my eyes) – I’m going to have to put on my sunglasses.” Listen:
In 2011, on the occasion of the death of Amy Winehouse, Prince revisited the song, this time in a more discreet way. The artist accompanied the singer Andy Allo on guitar in a more introspective version of “Love is a Losing Game”which can be seen below.
Prince left us in 2016, just five years after Amy Winehouse. Despite belonging to completely different generations, both artists left extremely important marks on music and are celebrated to this day.
Collaborated: André Luiz Fernandes.
Source: Rollingstone

Earl Johnson is a music writer at Gossipify, known for his in-depth analysis and unique perspective on the industry. A graduate of USC with a degree in Music, he brings years of experience and passion to his writing. He covers the latest releases and trends, always on the lookout for the next big thing in music.