“Love Is A Losing Game” by Amy Winehouse

"Love Is a Losing Game" is the hush at the heart of Back to Black, Amy Winehouse's second and final studio album, from 2006, a song she wrote alone whose title says plenty about how she saw romance. Mark Ronson produced it and Gabriel Roth arranged it, with Homer Steinweiss on drums, Nick Movshon on bass, Thomas Brenneck and Binky Griptite on guitars, Victor Axelrod on piano, and a full string section, saxes, trumpet, trombone and harp swelling around her.

It went out late in 2007 as the album's fifth and last single, the final one released in her lifetime, and it was the lowest charting of the lot, though it climbed back after her death. The admirers were heavyweights: George Michael took it to his desert island above all his other picks, and Prince began playing it live and brought her onstage at The O2 to sing it with him.

Written with AI assistance from RockLists chart data, MusicBrainz and Wikipedia.