What is the Saddest song ever written? - Page 40

^Good choice.  I like the original (incongruous no?), but Gary's version is especially poignant.  I still haven't seen Donnie Darko, one day...

Surprised no one has mentioned this alternative classic:

Then there is any number of songs by Dead Can Dance, including this classic:

another video, but same song, here:

http://www.youtube.com/watch?v=1U-s8eLCcQk

And another:

Nick Cave & Kylie Minogue - Where The Wild Roses Grow

Nick Cave also does a killer version of this, but Buckley's version rules:

For a song that was a big hit on alternative and New Wave dance floors back in the 80's this song is actually rather sad:

Leonard Cohen's version of Hallelujah is pretty good too.

How about "These Days" by Jackson Brown, as performed by Tom Rush?

And Shangrila by the Kinks.

- Ed

Richard and Linda Thompson - "Dimming of the Day"

Katatonia's "In The White" is pretty melancholy in my opinion. Just thinking of that main melody that seems to just spiral downwards forever gives me goosebumps. 

"So i found you

found the way all through
the quiet cold of inner darkness
now that you're here
it becomes so clear
i have waited for you always"

Peter Gabriel - "Here Comes the Flood"

When the night shows
The signals grow on radios
All the strange things
They come and go, as early warnings
Stranded starfish have no place to hide
Still waiting for the swollen Easter tide
There's no point in direction we cannot
Even choose a side.

I took the old track
The hollow shoulder, across the waters
On the tall cliffs
They were getting older, sons and daughters
The jaded underworld was riding high
Waves of steel hurled metal at the sky
And as the nail sunk in the cloud, the rain
Was warm and soaked the crowd.

Lord, here comes the flood
We'll say goodbye to flesh and blood
If again the seas are silent
In any still alive
It'll be those who gave their island to survive
Drink up, dreamers, you're running dry.

When the flood calls
You have no home, you have no walls
In the thunder crash
You're a thousand minds, within a flash
Don't be afraid to cry at what you see
The actors gone, there's only you and me
And if we break before the dawn, they'll
Use up what we used to be.

Lord, here comes the flood
We'll say goodbye to flesh and blood
If again the seas are silent
In any still alive
It'll be those who gave their island to survive
Drink up, dreamers, you're running dry.

Still Alive - GLaDOS (VALVE)

It is very hard to understand the true message behind the song, even after playing the game. Here's a good reference. Warning spoilers.