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Natface’s 10 Best Break-Up Songs

It’s the end of the year, and everyone’s making listicles. Never one to miss the fun, I’ve compiled my top ten break-up songs, the ones that truly, no matter my mood or situation, stir the heart and make me contemplate how deeply personal each romantic interaction is, and how universal, and how earth-shaking, and how seriously normal. Here they are, in order:

1. Fiona Apple’s oeuvre, but specifically, Parting Gift

Parting Gift is the most perfect break-up song to me, not least of why is the line “I bet you could never tell/that I knew you didn’t know me that well.” It’s recriminatory, it’s wistful (“It ended bad/but I love where we started”), it’s aggressive, it makes me want to get into a relationship just to end it and listen to this song. 

2. Wish the Worst — Old 97’s

This song makes me wax lyrical. Hearing it live is always transcendently sad; something about Rhett Miller’s keyed up panic plays perfectly with the lyrics. “Why aren’t you here?” is the first plaintive line, and it only gets more desperate from there. “Every drink’s one more defeat”, indeed. The visual of a man sitting in his girlfriend’s empty home is too strong to resist, and the pathetic sentiment of wishing the worst on your exes is one I’m all too familiar with. 

(Look, I could only find YouTubes where the audience is all singing along; buy the song on ITunes, trust me, it is worth it.)

3. I Just Don’t Think I’ll Ever Get Over You — Colin Hay

What to say about this song except that it’s devastating in a new way each time you listen to it? “Without you here there is less to say.” Without this song there is no break-up song tumblr. Because what if it’s true? What if the worst is true and you never get over that ex? Colin Hay’s seminal break-up song is serene, accepting, and unbelievable to listen to.

4. No Children — Mountain Goats

The other two contributors placed this song as their number one, and their reasons are good. “I hope you die/I hope we both die” is perfect and simple and matter-of-fact and True.

5. Don’t Think Twice, It’s All Right — Bob Dylan

Dylan’s whole catalog is great for misery, but this one, he’s in control, he’s hitting the road, and it’s got that smug little twang to it. I’ve got a personal connection to it, as my college ex’s roommate sang this to himself after breaking up with his girlfriend one night. He sang it gleefully, adding various epithets into it as he went, and ended on a hiccup of almost-tears. For that alone, it’s in this list.

6. Heartless — Kanye West

Kanye consistently surprises me with songs that you would not expect from an egotistical maniac. The content of this song (which is where I go when I go with a break-up song, and I think the other two guys on here don’t, as much) is truly fascinating. Kanye has been hurt, and bad, and though it’s got his trademark ego — the “Never find anyone better than me” howl — Kanye’s confidence has been been badly shaken by a lady. The beat’s not bad, either.

7. Famous Blue Raincoat — Tori Amos (Leonard Cohen cover)

This is a poem, and I’m a sucker for an amazing poem. Tied up in small talk is an entire story, an entire tragedy, and it’s up to the listener to unravel it upon repeated listens. It could just be a letter to a friend, but it’s betrayal and jealousy and anger and regret, all in a little line “Sincerely, L. Cohen.” And Tori Amos’s voice is the perfect vessel for it.

8. Everything Reminds Me of Her — Elliott Smith

For touching on the most prevalent feeling after a break-up. You walk down a street, and that street is the one where he touched your hair and clasped you to him, telling you for the first time he thought you were beautiful. You go into a bar and the spectre of him is in a corner, asking you to move to Rome with him one day. A leather jacket, the smell of a cologne, Tom Waits, someone’s smirk, a subway ad, Philadelphia — everything reminds you of him. It’s stark and true and necessary to have this song in your arsenal.

9. Fuck You — Cee-Lo Green

A recent addition, but I think impossible to leave out. Beyond how popular the song was, it’s truly wonderful as a testament to the vacillation between outright anger and wounded wailing we all do after a break-up. And god, that chorus.

10. Untouchable Face — Ani DiFranco

Ani’s song features a very definitive “Fuck you” as well, Cee-Lo. I have a live version posted here that has a little of Ani’s trembling voice, and her half-laugh as she curses her former lover. It’s so, so human, and down there in the hole that you must surface from, and it’s also angelic in its pain. 

with a very special mention to Gaga’s Bad Romance. Because DON’T BE FRIENDS.