Wonder why nobody mentioned songs from Damien Rice. Nearly every song from him makes you want to cut your arteries and just call it a day.
Edited by wberghofer - 7/4/11 at 10:03am
The Lonesome Death of Hattie Carroll, by Bob Dylan (1963 or 64). It's rather lengthy. You have to bear with him as he tells a story. You need to listen to the entire story, and then the zinger is right at the end.
Another one worth mentioning is John Brown, also by Bob Dylan (a very rare song, which is available on his MTV Unplugged Live album (1995).
This is a very sad one indeed. As a matter of fact, if I'm not mistaken I believe even Dylan gets choked up while singing it at one point.
This song will absolutely tear you up on the inside, though.
"Letter to Hermione" is a song written by David Bowie in 1969 for the album Space Oddity. This ballad is a love letter to Hermione Farthingale, whom Bowie met through Lindsay Kemp. She became Bowie's girlfriend and they lived together for a short while in London in 1968. In early 1969 she left Bowie for Stephen Reinhardt, an American musician and dancer she met on the film Song of Norway.
The hand that wrote this letter
Sweeps the pillow clean.
So rest your head and read a treasured dream.
I care for no one else but you.
I tear my soul to cease the pain.
I think maybe you feel the same,
What can we do?
I'm not quite sure what we're supposed to do.
So I've been writing just for you.
They say your life is going very well.
They say you sparkle like a different girl.
But something tells me that you hide
When all the world is warm and tired.
You cry a little in the dark,
Well so do I.
I'm not quite sure what you're supposed to say,
But I can see it's not okay.
He makes you laugh.
He brings you out in style.
He treats you well
And makes you up real fine.
And when he's strong,
He's strong for you.
And when you kiss
It's something new.
But did you ever call my name
Just by mistake?
I'm not quite sure what I'm supposed to do.
So I'll just write some love to you.
I agree with you about James Taylor's 'Fire And Rain'. Good selection (for a very sad song). I remember listening to it one time, and REALLY feeling the pain he was expressing he was going through.
Bob Dylan has a lot of good material along these lines too. Pretty much everything on 'Blood on the Tracks' is like this, as well as a song on his 'Street Legal' album ('Where Are You Tonight (Journey Through Dark Heat)')
Andvari is another sad song from Sigur Ros. Specially the last part. Makes you want to cry, but then it comforts you.