The song Hallelujah is pretty damn draining.

"Holocaust" by Alex Chilton/Big Star, particularly the Sister Lovers version, but really every version out there including This Mortal Coil's. I can't think of anything more convincingly bleak.

Thanks to Clone, i can't get that Felt song outta my head now. It's all good, though.

I finally got Pere Ubu's Why I Hate Women about a week ago. "Stolen Cadillac" is perhaps my favorite sad song as of right now.

This as well!

Yeah i'd go with that. As with Hey being sad I ask you:
How?
It's generally upbeat save the chorus.

I might be wrong
I might be wrong
I could have sworn
I saw a light coming on

I used to think
I used to think
There is no future left at all
I used to think

Open up, begin again
Let's go down the waterfall
Think about the good times
And never look back
Never look back

What would I do?
What would I do?
If I did not have you?

Open up, let me in
Let's go down the waterfall
Have ourselves a good time
It's nothing at all
Nothing at all
Nothing at all

This song is just stunning.

oh YES!

I agree on "Dreamin'" by Lou Reed. The whole "Magic and Loss" album is terrible, but that song is plain devastating.
Also, "Danny Boy" and "Give my love to Rose" by Johnny Cash.
And "Helpless" by Neil Young.
All the songs above make me cry when I listen to them.

"Dreamin'" by Lou Reed

If I close my eyes I see your face
And I’m not without you
If I try hard and concentrate
I can still hear you speak
I picture myself in your room by the chair
You’re smoking a cigarette
If I close my eyes I can see your face
You’re saying, "I missed you"

Dreamin’, I’m always dreamin’

If I close my eyes I can smell your perfume
You look and say, "hi baby"
If I close my eyes pictures from China
Still hang from the wall
I hear the dog bark I turn and say
"what were you saying?"
I picture you in the red chair
Inside the pale room

Dreamin’, I’m always dreamin’

You sat in your chair with a tube in your arm
You were so skinny
You were still making jokes
I don’t know what drugs they had you on
You said, "I guess this is not the time
For long term investments"
You were always laughing
But you never laughing at me

They say in the end the pain was so bad
That you were screaming
Now you were no saint but you deserved
Better than that
From the corner I watched them removing things
From your apartment
But I can picture you red chair and pale room
Inside my head

If I close my eyes I see your face
And I’m not without you
If I try hard and concentrate I can hear your voice saying
"who better than you"
If I close my eyes I can’t believe that
I’m here without you
Inside your pale room your empty red chair
And my head

Dreamin’, I’m always dreamin’
Dreamin’, I’m always dreamin’
Dreamin’, I’m always dreamin’

How?

Defiently, the early Red House Painters are so depressing.

I agree

You guys have named a bunch.

---
Ballad of Hollis Brown by Bob Dylan

"Famous Blue Raincoat" by Leonard Cohen
"She's Real" by Kicking Giant
"Nothing Compares 2 U" by Sinead O'Conner

i can't believe i forgot it.

Part of me feels like I've been baited and that I'll be mocked for jumping in to correct some small classical music thing, but I can't help myself..... Sorry Glicey.

Mahler wrote many traditional Lieder, but they're not that well known. At least compared to his orchestral songs, which are very well known. In particular are the Kindertotenlieder (Songs on the Death of Children) and Das Lied von der Erde (The Song of the Earth). As you might imagine, there are some pretty sad songs to be found there. He also included songs in some of his symphonies; the 4th movement of his 2nd symphony is an orchestral song from Des Knaben Wunderhorn. The title is "Urlicht," which means Primeval Light, more or less. It is pretty sad.

I know a lot of people though would mention Strauss's Vier Letzte Lieder--the last things he wrote. I'm not super familiar with them. They're orchestral songs too. Three of the texts are by Hermann Hesse, who I know is popular among some people here. I need to get a recording of them.

Lou Reed- The Bed

Yeah, that one's up there too.

"I Knew That You'd Leave" by Jandek should also be on the list.

Xiu Xiu - Little Panda McElroy

this one's bitter as hell too.