Imagine that.
none of that whiny shit, fuck that shit.
I'm talking Casimir Pulaski day by sufjan, or porcelain by the peppers.
comon motherfuckers. I have some weeping to do.

http://www.youtube.com/watch?v=N090STPx-2M

Elliott Smith - Miss Misery
http://www.youtube.com/watch?v=zH8-lQ9CeyI

Flowers from the man who shot your cousin (http://www.last.fm/music/Flowers+From+The+Man+Who+Shot+Your+Cousin/Hapless)

Sad as fuck.

Valient Thorr's "Ballad of the Morning Star" is awkwardly creepy, though its not on YouTube.

I know I say this to every one of these kinds of threads, but:

"Land-Locked Blues" by Bright Eyes, from 'I'm Wide Awake, It's Morning'.

My roommate would like to contribute "Yesterday", by the Beatles. That's another good one.

http://ca.youtube.com/watch?v=LwiVpZy8DFY

http://www.youtube.com/watch?v=5W4YmavHnFw

It's under two minutes long and instrumental, but it still makes me cry.

Solitude - Black sabbath

http://au.youtube.com/watch?v=MQBT5Gwp2A0

"A Spindle, a Darkness, a Fever and a Necklace" by the Bright Eyes, "Black Orchid" by Blue October and "Is it Real" by the Seatbelts are some of the saddest songs I know.

Two Gallants - Up The Country
Two Gallants - All your Faithless Loyalties
Two Gallants - Waves of Grain
Two Gallants - Some Slender Rest
Two Gallants - Threnody

Hell, pretty much anything by Two Gallants. Although it's sad in a really hopeless way, it still counts.

Have a listen to the album Aegis by Theatre of Tragedy.

"Mad World" - Gary Jules
"Hallelujah" - Jeff Buckley
"Satisfied Mind" - Jeff Buckley
"John Wayne Gacy Jr." - Sufjan Stevens

Pretty much anything by Explosions in the Sky.

Oh yeah, "Suzanne" by Leonard Cohen

Dinosaur Jr. - Feel the Pain
Dinosaur Jr. - Been there all the Time

Trying to cover some different artists:

Most everything by Nick Drake.

Joy Division obviously have a (deserved) reputation in the field. The track "Decades", however, probably takes first place. The word here is not just "sad", it's "grief".

"Postcards From Italy" by Beirut always makes me want to fucking weep. The line "The times we had ... Were not all bad" is, in my mind, permanetly associated with the summer I spent with one of my best friends while she watched her remaining parent die of cancer - it may be the perfect summary of hopeless and desolate failure. Your mileage may vary.

Quite a few things by Blonde Redhead - "Misery Is A Butterfly", "Led Zep" and "23", for example.

"Knockin' On Heaven's Door", and "Boots Of Spanish Leather" (sort of) by Bob Dylan. Also, the Sonic Youth cover of "I'm Not There".

"Accidentally Like A Martyr" by Warren Zevon, covered by Jerry Garcia. Zevon was a fucking genius, but most of his music, although incredibly dark, was too funny to be in this thread.

"Theme For Gabor" by Gabor Szabo may well be the most elegant cry for help ever put to record. Instrumental.

"The Thrill Is Gone" by Chet Baker. If you find yourself listening to this frequently for more than a week or two, you are fucked.

"The River" & "The Ghost Of Tom Joad" by Bruce Springsteen.

"Cold White Christmas", "Young Shields" & "I Love Creedence" by Casiotone For The Painfully Alone. Yeah, I know, but this is good shit.

"Testarossa Autodrive" by Kavinsky has always seemed incredibly melancholy to me, even though you could probably use it in a european car advert without raising eyebrows. I think it's the synth line. Is sounds like a robot asking you why you broke it's heart. This will get stuck in your head.

"Denko" by Kante Manfila. I don't know what the fuck language this is in, but I'm fairly sure it's sung by the souls of drowned children.

"Sposa Son Disprezzata" performed by Cecilia Bartoli, from the opera Bajazet. Desolation.
"Vesti La Giubba" performed by Enrico Caruso, from the opera Pagaliacci. Christ.
"The Cold Song" by Klaus Nomi, adapted from the opera King Arthur.

I could go on, but I won't. For a long time I was hardcore into making myself more miserable and, accordingly, got a lot of shit for enjoying music that made other people want to slash their wrists and having the gloomiest record collection ever. Despite that, I can't hear "When The Night Feels My Song" by Bedouin Soundclash without wondering why the fuck everybody isn't crying.

Sonic Youth's cover of "Superstar", I think originally by The Carpenters(?).

Not sad sad, but whatev

James Taylor - Fire and Rain.


Shut up and cry

Bread was one of the original bands for sweet, sad and simple acoustic ballads.

My two favorites that can still get to me at times are "Aubrey" and "Everything I Own"

http://www.youtube.com/watch?v=dwdTcoUHfkw

Generique - miles davis

although some people may contest it is just depressingly cool.

The Vanishing Act - Bright Eyes

Sorry if there's been too many of their songs suggested. Conor just puts alot of emotion into his songs.

Summoning's Land Of The Dead on Oath Bound is quite depressing. I'm not sure if I'd label it as sad, but its in a minor or diminished scale for sure. The arpeggios are madly diminished?

Immortal Technique - You Never Know

Buckethead - Watching the Boats with My Dad