Come on! He may have "made the song his own," but a cover is never a true expression of anything.

Xiu Xiu - "Knife Play", "Apistat Commander"
Cat Power - "Troubled Waters", "Names", "Faces"
Elliott Smith - "Lived In Bars"

Sinking Belle-Boris and SunnO)))
In My Garden-Swans

Caroline Says 2- Lou Reed

Beautifully depressing.

Agreed about "Nightporter" by Japan. Bleak.

I also nominate "Laguna Beach" by The Legendary Pink Dots and "The Stagnant Pool" by Felt.

Brilliant choice. The instrumental coda is a blatant explanation as to why Mogwai have always been fans of Felt, even though the song itself i associate more with melancholia rather than full on sadness.

"Dirt In The Ground" - Tom Waits

or

"There You Are" - The Flaming Lips

The Cure - Cold
Purcell - Dido's lament from Dido & Aeneas
Beach Boys - Caroline No
Neil Young - Tired eyes

JT said Joy Division- New Dawn Fades and that is one of my top sad songs.

I'd throw in
Velvet Underground- Pale Blue Eyes
Television- Marquee Moon (that song makes me horribly depressed)
Bauhaus- Crowds
David Bowie- Five Years
The Pixies- Hey

I can't think of a particular one right now, but seen as New Order have already been mentioned, i'll go for 'Elegia'. The full 17 minute+ version is just majestic.

I'm tempted to say something by Mahler, but he never wrote any songs, to my knowledge.

I've just told Mama goodbye by Hank Williams is the saddest that springs to mind from his Hank stuff. I couldn't pick anything from the Luke the Drifter stuff... that's easily the most successfully bleak stuff I can think of.

Dolly Parton's I will always love you.
Laura Cantrell's Bees/ When the roses bloom again
Kenny Roger's Lucille... in fact, just thinking about it makes me want to blubber.
And there's a few rock songs and a few proper pop songs that I can think of, but I can't be arsed with explaining why. Basically, it's all about country.

I refer Mr 'krack', if this is your real name, to the general covers work of Diamanda Galas, Otomo Yoshihide, Roland Kirk's version of I say a little prayer, Keiji Haino's See that my grave's kept clean and Soft Cell's version of Tainted Love.

There are plenty more songs that either get to the core of a song, or find a personal identity within another person's song. Until Girls Aloud released their fourth utterly magnificent proper pop song, I flirted constantly with the notion that there were too many songs, and covers were the only way forward.

Great one. One of my favourite songs ever; Dolly at her very best.

The Smiths - Still ill, Back to the old house (Hatful of hollow version), I know it's over, Never had no one ever, Asleep

Serge Gainsbourg - Je suis venu te dire que je m'en vais, Manon, Valse de Melody

Jane Birkin - Baby alone in Babylon

Agreed. My Coat of many colours tugs in a similar fashion. I should've stipulated that I was referring to the 70s version of I will always love you rather than the 80s one, which was good but not 'please make the pain stop' good.

A Few come to mind but the main ones are

The Smiths - Meat is Murder
Radiohead - How to disappear completely

Nick Drake - Way to blue, Day is done, Fruit tree
Tim Buckley - Love from room 109... , Dream letter, Chase the blues away, Once I was, Phantasmagoria in two, Morning glory

Lifetime achievment by unwound.
Who by snuff
That song at the end of the tremelo ep by my bloody valentine

radiohead - let down
fushitsusha - that which is becoming to me
cat power - the color and the kids
the gathering - shrink
ornette coleman - lonely woman (the melody has such a sad character).
the replacements - here comes a regular
minor threat - look back and laugh
bardo pond - isle
yo la tengo - green arrow
the vast majority of suishou no fune's output.

plus a lot of stuff by jack rose and ancient blues.

Oh, hell yes.

His name was Perry
He had learning difficulties
His father was a very mean man
His father burned his skin
His father sent him to his death
He was ten years old
He was ten years old
He was ten years old

Her name was Naomi
Beautiful round face, so ashamed
Taught me how to please a man
After school in the back of a bus
She was doing it every day
She was eleven years old
She was eleven years old
She was eleven years old

Her name was Sheryl
Black hair, like an electric space
She would pretty paint my face
She was a very good friend
Her father would come to her in the night
She was twelve years old
She was twelve years old
She was twelve years old

His name was Donovan
He was a very good friend
The cards were stacked against him
He was selling cocaine
The last time I saw him
He was thirteen years old
He was thirteen years old
He was thirteen years old

His name was Charles
He said he was in love with me
We were both fourteen
Then I had to move away
Then he began to smoke crack
Then he had to sell ass
I don't know where he is
I don't know where they are