Songs that break your heart:

Nicest Thing-Kate Nash

When Dolly sings I Will Always Love You to Burt Reynolds.

@ilikedginger: Ohh, is good.

Good Morning, Heartache-Bille Holiday
I Fall to Pieces-Patsy Cline
Someone to Watch Over Me-When pretty much anyone sings it

wtf, why would I type sweet instead of "queen"?

x-ray style - joe strummer
ball and chain - social distortion
redemption song - johnny cash & joe strummer

i'm sure there's more

Nothing Better - Postal Service

Seconded on Hurt and Casimir Pulaski Day.

Pain - "Excalibur"

Priests + Paramedics by Pedro the Lion

@Jas: +1 for Cash's Hurt

"Haligh, Haligh, a Lie, Haligh" - Bright Eyes
"Konstantine" - Something Corporate
"Perfect Day" - Lou Reed
"More Than This" - The Cure
"One Tree Hill" - U2
"Youngstown" - Bruce Springsteen
"Cathedrals" - Jump Little Children
"Disarm" - The Smashing Pumpkins

If you've never heard Youngstown (and you probably haven't) I highly recommend it. The rest of these songs describe, at most, the pain of one person's whole life. Youngstown describes the pain of an entire people, and one that you've probably not heard described before, at least not so eloquently.

I Will Follow You Into the Dark-Death Cab for Cutie
@giu: I was about to make Harry Potter joke and decided against it because I dont want to reveal how big a dweeb I am quite this early in the morning.

god, so many... i'll start with:

If You're Not The One (acoustic version) by Daniel Bedingfield
Stay (covered) by Jonah Matranga
Forever by Ben Harper
Breathe Me by Sia