"Love Is a Losing Game" is a song written and recorded by English singer-songwriter Amy Winehouse for her second album Back to Black (2006). The track was chosen as the fifth single from the album. The single was released on December 10, 2007 in the United Kingdom. The song was added to BBC Radio 1's playlist on November 7, 2007.
George Michael named the song as one of his eight choices on the BBC Radio Four programme Desert Island Discs. When asked which of his eight choices he would pick if he had to choose one, he opted for "Love Is a Losing Game". Prince has taken to covering the song live. On September 21, 2007, he was joined onstage by Winehouse at the final aftershow of his 21-gig marathon at The O2, and they performed the song together.
The song is the lowest-charting of Winehouse's Back to Black singles, peaking at number forty-six on the UK Singles Chart and spending four weeks on the UK Top 100 (46-61-76-98).
Winehouse performed "Love Is a Losing Game" live when she appeared at the 2007 Mercury Prize. She later performed it at the 2008 BRIT Awards. The song won the award for Best Song Musically and Lyrically at the 2008 Ivor Novello Awards on May 22, 2008, Winehouse's third award at the event.
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