all of Berlin and Magic and Loss by lou reed and the buzzard song off miles davis porgy and bess. and Prristina is tot'es right about that Rhianna song, its really really dark, ilove it.

Jens Lekman - Past, Present, Future

Death In June - Fall Apart
Current 93 - Sleep Has His House
The Shangri La's - I Can Never Go Home Anymore
Nico - Secret Side/ These Days
Bob Dylan - Positively 4th Street (Perhaps it's more angry than sad)
Dizzie Rascal -I Luv U
Ice Cube - It Was A Good Day
The Smiths - Never Had No One Ever
Judy Collins - Send In The Clowns

Big Louise (Scott Walker)

She stands all alone
You can hear her hum softly
From her fire escape in the sky
She feels the bags
Need her eyes with the moon beams
And cries 'cause the world's pass her by

Didn't time stand still yesterday
In a world full of friends
You loose your way

She's a haunted house
And her windows are broken
And the sad young man has gone away
Her bathrobe is worn
And tears smudge her lipstick
And the neighbours just whisper all day

Didn't time stand still yesterday
In a world full of friends
You lose your way


If You Go Away (Jacques Brel)

If you go away
On this summer day
Then you might as well
Take the sun away
All the birds that flew
In the summer sky
When our love was new
And our hearts were high
And the day was young
And the night was long
When the moon stood still
For the nightbird song
If you go away
If you go away
If you go away

But if you stay
I'll make you a day
Like no day has been
Or will be again
We'll sail on the sun
We'll ride on the rain
And talk to the trees
And worship the wind
But if you go
I'll understand
Leave me just enough love
To fill up my hand
If you go away
If you go away
If you go away

If you go away
As I know you will
You must tell the world
To stop turning, turning
Till you return again
If you ever do
For what good is love
Without loving you
Can I tell you now
As you turn to go?
I'll be dying slowly
Till the next hello
If you go away
If you go away
If you go away

But if you stay
I'll make you a night
Like no night has been
Or will be again
I'll sail on your smile
I'll ride on your touch
I'll talk to your eyes
That I love so much
But if you go
I won't cry
For the good is gone
From the word
Goodbye
If you go away
If you go away
If you go away

If you go away
As I know you must
There'd be nothing left
In the world to trust
Just an empty room
Full of empty space
Like the empty look
I see on your face
And I'd've been the shadow
Of your shadow
If you might've kept me
By your side
If you go away
If you go away
If you go away

But if you stay
I'll make you a night
Like no night has been
Or will be again
I'll sail on your smile
I'll ride on your touch
I'll talk to your eyes
That I love so much
But if you go
I won't cry
For the good is gone
From the word
Goodbye
If you go away
If you go away
If you go away

Yes, Scott 3 is particularly sad (If I remember well he made it after a breakup).

Ne me quitte pas by Nina Simone is quite sad too (it's probably my favorite version of the song), as are her versions of Lilac Wine and Strange fruit.

I'm more familiar with Marc Almond's versions of those two songs (Big Louise and If You Go Away), on Untitled, an album made while he was a very fucked up little boy. I find that whole album to be pretty despairing and difficult to listen to.

For some reason, "Agent Orange" by Depeche Mode sounds very sad to me.

Talking of Marc Almond - Melacholy Rose or Stories Of Johnny

Try hard to make the world look bright today
Try hard to make my nightmares go away
Try hard to keep the fear away
The cold of day, try hard
Try hard to play the games the world would like you to play

But people, they don't really listen
Their smiles are the keys to the prison
I'll call on the angels, to hold my head softly
They'll always remember . . . Stories of Johnny

Try hard to make my anger go away
Try hard to make my money last the day (no way)
Try hard to keep away the pain
Stop the rain, try hard
Try hard to fly a thousand miles away

But people, they don't really listen
Their smiles are the keys to the prison
I'll call on the angels, to hold my head softly
They'll always remember . . . Stories of Johnny

J Mascis and The Fog's "Free So Free" is beautifully sad... plus wanky ballad solo