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15. Bright Eyes, "Land Locked Blues" (2005)
Conor Oberst might have the voice of an petulant kitten, but he knows his way around a set of lyrics. "Land Locked Blues" is an existential crisis filmed through the lens of a relationship, and Oberst's lyrics, pulling the rare trick of being specific and universal, gain extra force from guest vocals by Emmylou Harris, who sounds like a full-grown cat. — A.H.
14. Feist, "Let It Die" (2004)
"Let It Die" lands somewhere between melancholic and out-and-out heartbreaking, like Feist's voice itself. But this track isn't just beautifully sung — it's beautifully written. With lines like "The saddest part of a broken heart/Isn't the ending so much as the start," this song captures the pain of letting go of your hopes. — R.K.
13. Black Keys, "10 A.M. Automatic" (2004)
You can't really talk about the aughts (is that what we're calling them?) without talking about The Black Keys. They helped revive garage rock (again) and gave us gritty-but-accessible songs like "10 A.M. Automatic." This breakup song is all about a Jekyll/Hyde situation, where someone you date seems to have two faces. Listen to this one when you just can't take their drunk face anymore. — R.K.
12. Bon Iver, "Skinny Love"
If you're trying to make haunting breakup music, heading into exile in the woods of Wisconsin is almost cheating. But the results speak for themselves. This is heartache on a different level; sadness for the one who left and remorse for the person you've become. — J.G.
11. Beyonce, "Irreplaceable" (2006)
The best thing about "Irreplaceable," other than the usefulness of "to the left, to the left" in everyday conversation, is the surprise revelation in the second verse: "Oops, I bet you thought that I didn't know/What did you think I was putting you out for?" Upon discovering her boyfriend's unfaithfulness, Beyonce doesn't fall apart or even get angry. There's no confrontation, no discussion, no argument. Instead she coolly reveals to him what she knows, and introduces her new man in the same move. It's textbook Beyoncé: classy, empowered, and possessed of a wicked sense of humor. — Natasha Ochshorn