This song is about Amy Winehouse as an archetype, but not so much about her specifically. It’s for the Amys of the world, who for whatever reason can’t resist the lure of self-destructive behavior. John Darnielle sings it like a prayer, wishing the Amys well while knowing that things probably won’t work out for them. There is no condescension in this song. If anything, the Amys are valorized for their bravery, and Darnielle gently suggests that what most of us might consider a sensible, responsible way of living is just a form of cowardice. It’s refreshing to hear this much empathy for a type of person who is typically insulted, or celebrated for the wrong reasons.
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