In the haunting ballad “Love Is a Losing Game,” Winehouse reflects over her painful moments of loneliness and confusion, as well as her inability to rewrite history and change how her relationship ended. Despite the song’s raw reflection on her love, she prefaced a 2006 live performance of the song by saying:

This is my favourite song from the new album. I always get a little teary when I play it.

Following her sudden split with Blake Fielder-Civil, Winehouse took a vacation to Spain with her family and purchased a guitar from a local vendor, which is what sparked the writing of “Love Is a Losing Game.”

The whole song, comprised of three verses that each contain slightly varying quatrains, is an extended metaphor, with allusions to love being some sort of unfair game closing each verse.

While Winehouse has often been considered one of the best songwriters of her time, “Love Is a Losing Game” specifically has garnered attention for its simplistic, yet powerfully deep lyrics. In 2008, two years after the song’s release, the University of Cambridge included the second and third verses on a practical criticism exam for their English students.

In celebration of the 13 year anniversary of the song’s release as the fifth and final single off Back to Black, the Amy Winehouse Foundation released an official animated lyric video on December 10, 2020.