“Love Is a Losing Game” is a song by English singer and songwriter Amy Winehouse from her second and final studio album Back to Black (2006). It was chosen as the fifth and final single from Back to Black. It was the final single released in Winehouse’s lifetime. The single was released on 10 December 2007 in the United Kingdom. The song was added to BBC Radio 1’s playlist on 7 November 2007.
A video shoot was set up for “Love Is a Losing Game”, reportedly costing £70,000 at Pinewood Studios, but an unnamed source was quoted in The Sun as saying that it was cancelled after Winehouse failed to turn up for filming. The original video was supposed to be directed by Phil Griffin and shot by director of photography Adam Frisch. Two alternate music videos were released: the first is a montage video, which includes photographs of Winehouse alongside live performance clips of the song, and the second is an entirely live video, taken from her I Told You I Was Trouble live performance DVD.