The 25 Most Exquisitely Sad Songs in the Whole World: No. 17

'Back to Black'
Amy Winehouse (2006)

The Breakdown: An ominous song of impending misery following infidelity, sung by a woman with her departing lover's name tattooed on her chest.

The Waterworks: "You go back to her/And I go back to black."

Casualty Count: A lover. Sobriety? Sanity?

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