"Love Is a Losing Game" is a song written and recorded by English singer and songwriter Amy Winehouse for her second album Back to Black (2006). The track was chosen as the fifth single from the album. It was the final single released in her lifetime. 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 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 21 September 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.[1] The song is the lowest-charting of Winehouse's Back to Black singles, peaking at number 46 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.[2] 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. In 2015, Sam Smith recorded a cover of the song for the re-release of his debut album In the Lonely Hour (Drowning Shadows Edition). The same year, a documentary film, directed by film maker Asif Kapadia was released; that depicts the life and death of Winehouse, entitled as Amy. Winehouse's performance of the single at the Mercury Prize in 2007 was included in the film and as was also featured on the original soundtrack.