Saddest Song Ever

[Huw]

"Set the Fire to the Third Bar" - Snow Patrol
"This Woman's Work" - Kate Bush
"Song to Say Goodbye" - Placebo (although it's the video which makes that really depressing)

 

[Kid Charlemagne]

A loop tape of Morrissey?

On a more serious note - the lament for Gandalf from the Fellowship of the Ring soundtrack would be good - it's pretty much wordless, and should trigger a response in most geeks, even if they don't consciously remember exactly what it is.

 

[Felix]

Adagio for Strings, by Samuel Barber

It is incredibly mournful and introspective; it was used masterfully in Oliver Stone's "Platoon".

Gollum's Song as sung at the end of LoTR: the Two Towers

Seconded.

 

[Clavis]

Try these:

"Failure" by Swans
"Fall Apart" by Death In June
"Faith" The Cure

The first two two might be obscure, but I can guarantee you they are two of the saddest songs ever written.

 

[Switchblade]

"Set the Fire to the Third Bar" - Snow Patrol
"This Woman's Work" - Kate Bush
"Song to Say Goodbye" - Placebo (although it's the video which makes that really depressing)

To be fair anything by Placebo is quite depressing. I had to cut them from my MP3 player because the random function managed to put together a combo that meant I'd often come close to losing the will to live by the time I'd got to work every morning. Not exactly the early morning pick me up I was after.

Evanesance has some pretty depressing songs as well, cut for the same reason.

And as I am currently listening to it at the moment "A bullet named Christ" by Wednesday ain't exactly cheerful.

 

[B4cchus]

I'm seconding Felix's mention of Adagio for Strings, by Samuel Barber.
Also Hurt, by Nine Inch Nails (or the version done by Johnny Cash, YMMV)

BTW, the version with David Bowie hits the spot too.

While i'm at it.. add "Home" by Depeche Mode to the list as well.

 

[Random Axe]

What you REALLY want is Dead Can Dance, "The Host of Seraphim".

 

[Kahuna Burger]

"The Shortest Story" by Harry Chapin is very dark, but as implied by the title, kinda short. It's also really not background music, though as "songs sad enough to induce crushing despair" go, it's up there.

(According to wikipedia it was "named by author Tom Reynolds in his book I Hate Myself and Want to Die as the second most depressing song of all time". )

edit : well, about half Harry's songs fit the request, with Tangled Up Puppet, Cats in the Cradle and A Better Place To Be leaping to mind for both content and sound....

 

[occam]

Jill's theme from the Once Upon a Time in the West soundtrack is a good one; I could always get my dog to howl in seeming sympathy by playing it.

Barber's Adagio is great for this purpose as well, of course.

 

[Random Axe]

And hey, I might as well throw in BOC's "Don't Fear the Reaper" for a good fantasy-related song to induce crushing despair...