The Top 5 Songs That Will Break Your Heart

#5 Willing to Wait, Sebadoh
A friend of mine attended an acoustic Sebadoh show (in Boston) years ago, and told me while Lou Barlow sang this song, the girl it was written about was standing at the back of the club listening — with her current boyfriend.

Did you just hear that? Yeah… that was my heart, dropping out of my chest.

 #4 When We Two Parted, The Afghan Whigs
The entire album, “Gentlemen”, has been designed to destroy you – and is a tension filled climatic (and dramatic) end to a relationship exposed in Bob Gendron’s 33 1/3 on “Gentlemen”.  “When We Two Parted” maps out the recognition of the end of it all in one verse:

“Every night I spent in that bed with your face in the wall. If I could have only once heard you scream. To feel you were alive instead of watching you abandoning yourself.”

#3 Don’t Forget Me, Neko Case (cover)
If Neko Case’s voice isn’t enough to tear you into shreds, her cover of this already amazing (and sad) Harry Nilsson song will. Just download it now, and you’re welcome.

Actually, let’s just get this out of the way — here’s Neko singing “Don’t Forget Me” on Elvis Costello‘s show: Spectale.


#2 Ladies and Gentlemen We Are Floating In Space, Spiritualized
This song and I met at the end of the American version of “Vanilla Sky“, and we’ve been in a relationship ever since. Disclaimer: Prone to crying every time this song is played.


#1 The Humpty Dumpty Love Song, Travis
The heavy sigh at the very beginning of the song says it all: it’s going to rip your f***ing heart out. This will be the longest, and saddest 14 minutes of your life. That’s right, 14 minutes — listen to it all the way through, there’s a surprise at the end.

Now that I’m sullen and nostalgic about my own, I’d love to hear about your own heart break mixes — what are your favorites, and why?

Other recommendations (via Facebook and Twitter):
Make This Go On Forever, Snow Patrol
Skinny Love, Bon Iver
Without You, Harry Nilsson
Uninvited, Alanis Morissette
November Rain, Guns N’ Roses
Fly To The Angels, Slaughter
Lucky You, The National
I Know It’s Over, The Smiths
Gravity, Embrace


4 thoughts on “The Top 5 Songs That Will Break Your Heart

  1. That Sebadoh story must dovetail with the Boston-show Sebadoh story I’ve been told. Lou’s longtime gf had left him for the band manager; she’s at his Middle East Upstairs show, I believe with the new bf; somehow she and Lou end up going into one of the tiny next-to-the-upstairs stage with a bottle of wine and locking the world out. According to my source Lou told the audience this at a later Mid East Up show and concluded, with a flourish, “and now she’s having my baby!”

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