Saddest Song Ever

[Ringan]

Adagio for Strings, by Samuel Barber

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

That's what I would recommend. It was also played when FDR died. The only caveat is it is semi-frequently used in the media.

 

[Tinner]

Hate Me Today by Blue October
Hurt by Johnny Cash (Much sadder than the NIN version)
Wish You Were Here by Pink Floyd
Creep by Radiohead
Adams Song by Blink 182

Almost anything from the album "Everything Turns Grey" by Agent Orange, especially the title track.

 

[Man in the Funny Hat]

Yet another vote for Barber's Adagio for Strings. Try also The Death of Asa from Grieg's Peer Gynt.

 

[Kheti sa-Menik]

Folk songs. Now those are sad some of them.

"Who'll go Waltzing Matilda Eith Me?" is one of the saddest songs ever. Austrailian folk song. (Not to be confused with the actual "Waltzing Matilda" song which is referenced in the former song)

"Willie McBride" is a song covered by a few different bands, most notably the Clancy Brothers/Tommy Makem.

A two play of these songs will make you want to drink yourself into darkness.

 

[Deset Gled]

"Failure" by Swans

Wow, that takes me back. Swans has some very ambient and very powerful stuff that would be great for background music to gaming. "Failure" is currently available on the album "Various Failures". Other songs off of that album that would work well are "God Damn the Sun" and "Picture of Maryanne". I would also recommend some songs off of "Soundtracks for the Blind", such as "Helpless Child", "How They Suffer", "The Sound" and "Minus Something". FWIW, Swans stuff is really best when listened too in the context of an entire album, and you could probably set up the album to run in the background, and work on timing the sad things to happen when the sad songs come on. If you can find a copy of it, the album "Anhedoniac" by Jarboe (one half of Swans, the other half being Michael Gira) is one of the most emotionally powerful albums I know.

From classical music, I would recommed James Barnes Third Symphony, "The Tragic" Op. 89. This piece was inspired by the death of Barnes's infant daughter Natalie. The first movement is probably the best for your needs.

For stand alone songs, I have a personal list of the saddest songs ever. They may not work for your purposes, since the sadness in them partially comes from things other than just the sound (i.e. the lyrics, the performer, the experience), but they are:
3. Rocketman by William Shatner
2. Mandy by Barry Manilow
1. The Dangling Conversation by Simon and Garfunkel

 

[EricNoah]

Also Hurt, by Nine Inch Nails (or the version done by Johnny Cash, YMMV)

*shakes fist* You took mine!

 

[Captain Howdy]

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

I came into this thread to suggest this song. You really do want to use it!

 

[Presto2112]

I'll nominate Who Wants To Live Forever by Queen (from A Kind of Magic, aka the Highlander Soundtrack.)

 

[Tewligan]

It's called The Last Kiss, and is a cover; the original was done in the early-mid '60's by I forget who.

Wayne Cochran and the C.C. Riders.

If you can't remember the saddest song in the world, you can at least play a tribute. Jables and Rage Kage would be pleased.

 

[Ahnehnois]

A simple, instrumental, but haunting dirge: "Gentle Execution" from the Season III BSG soundtrack by Bear McCreary.