Breakup Songs Essentials

There’s a moment in the 2015 Amy Winehouse documentary Amy in which the singer, finishing up a demo vocal of the existentially bleak “Back to Black,” looks up from her mic with a giant grin spreading across her face and says, as though the song had come from someone else’s mouth, “Oh, it’s a bit upsetting at the end, isn’t it?” It is. But it’s cathartic, too, a ventilation system for feelings that would drive you crazy if you kept them inside too long. (Otherwise, why would Winehouse be smiling?) Angry, remorseful, nostalgic, and proudly defiant, here’s a playlist of classic breakup songs sent up like flares in the dark—because we know how it feels to feel like nobody knows how you feel.