For Amy Winehouse, "black" was shorthand for self-created oblivion: Whether by drugs or drinks or depression, the soul singer's muse was the act of unplugging. In her songs, embracing the void isn't portrayed as noble or even defensible, but rather as an unavoidable reflex in response to daylight bummers.

The title track for her watershed 2006 album is wrenching in how it portrays the inevitability of breakdown. She and her man part ways; he goes back to his old woman, and she, of course, goes back to black. This is Winehouse at her most tragically Winehousian: charmingly crude ("He left no time to regret / kept his dick wet"), cosmically morose ("I died a hundred times"), and stricken by the notion that fate always beats out free will ("Life is like a pipe / And I'm a tiny penny rolling up the walls inside"). It goes without saying Winehouse's death over the weekend multiplies the music's impact. But when she was still with us, the bottom line was the same--what a sad, gorgeous song.

On iTunes: Amy Winehouse / "Back to Black"