Sad songs

[Shro]

Because occasionally you just need a good cry.
Iron and Wine/Calexico - Dead Man's Will. Their entire EP together was heartwrenchingly good. (He Lays in the Reins and 16, Maybe Less are two also sob-inducing. Also the song Naked as we Came by just Iron & Wine.)
Taylor Swift ft. The Civil Wars - Safe and Sound Even if you don't like Taylor Swift, you should definitely give this song on the Hunger Games Soundtrack a chance.

[jobriath]

This acoustic version of Of Montreal's The Past is a Grotesque Animal burrowed into my head and remained there. I love its bitterness and wistfulness.

Edit: I couldn't get into the Iron and Wine stuff (Boy with a Coin is the only song of his?theirs? that I've really got behind) but Taylor Swift is a motherloving revelation!

Reedit (sorry, I am somewhat low on bloodsugar): This doesn't sound too depressing, though. Casimir Pulaski Day by Sufjan Stevens is the best song in the world about childhood bone cancer.

[SirMustapha]

The Wedding, by the Legendary Pink Dots.

And even though this one is very subjective, Message, by Vangelis.

[UniqueScreenname]

Nutshell - Alice in Chains
Bother - Stone Sour
How to Disappear Completely - Radiohead
Never Let Me Go - Florence + the Machine

Taylor Swift ft. The Civil Wars - Safe and Sound Even if you don't like Taylor Swift, you should definitely give this song on the Hunger Games Soundtrack a chance.

I heard this song on MTV and was extremely surprised it was Taylor Swift, since she sounded good. Now I've listened to it about 15 times in a row and am quite despondent, just like the thread was designed for.

[Annihilist]

Something I can never have - NIN

[Amie]

Wait for sleep - Dream Theater Doesn't matter if you like metal or not because this song isn't.
Her morning elegance - Oren Lavie Doesn't have a sad tune or anything but it's a beautiful song with a beautiful video.

[aldonius]

Three from Ben Folds Five:
Magic
Smoke
And of course Brick

[jobriath]

And of course Brick

Brick! I was going to post this. Your link is a repeat of the Smoke link, so I guess I will.

Edit to add:

Also the song Naked as we Came by just Iron & Wine.

Ouch. That is good.

[philsov]

Streetlight Manifesto - As the Footsteps Die Out Forever

Yes, depressing ska can actually exist. Muuuuch higher quality than the Catch 22 original.

[Izawwlgood]

Johnny Cash Hurt
Awesome cover.

[Annihilist]

Johnny Cash Hurt
Awesome cover.

I hate to be an elitist (not really) but the original is a lot better.

While we're talking Nine Inch Nails, (I am at least) there are a few other songs that fit this:

The Day The Whole World Went Away
Something I Can Never Have
The Great Below
Ripe [With Decay] (Instrumental but it sounds sad)

[Izawwlgood]

I hate to be an elitist (not really) but the original is a lot better.

I couldn't disagree with you more. Reznors version sounds whiny and angsty; Cash's version sounds nostalgic, insightful, and sorrowful.

[bosonicyouth]

Dirty Three - Everything's Fucked
Saw them for the fourth wonderful time last night and they played this. Sad times.

Also:
Red House Painters - Summer Dress
Mount Eerie & Julie Doiron - Who

[charliepanayi]

I hate to be an elitist (not really) but the original is a lot better.

I couldn't disagree with you more. Reznors version sounds whiny and angsty; Cash's version sounds nostalgic, insightful, and sorrowful.

They're both great versions in different ways (whiny and angsty? Maybe, but NIN are bloody good at whiny and angsty).

Anyway:

http://www.youtube.com/watch?v=Luirzce0UF8

[Annihilist]

I hate to be an elitist (not really) but the original is a lot better.

I couldn't disagree with you more. Reznors version sounds whiny and angsty; Cash's version sounds nostalgic, insightful, and sorrowful.

I guess i prefer the raw emotion and passion of the original

[SurgicalSteel]

In the context of the entirety of The Downward Spiral, I think Trent Reznor's version is better. As a song to listen to on its own, singularly, out of context of any album, I prefer Johnny Cash's. However, the same way my opinion of Reznor's version is colored by my opinion of The Downward Spiral as an album, my opinion of Cash's version is likely colored by the amazing video for it.

[UniqueScreenname]

I have to agree. I don't think the Johnny Cash version would have been such a big deal if the video wasn't so heartbreaking. I always sort of lean towards the original because those words had to have come from somewhere, and so the song, to me, will always seem more genuine with NIN because Trent Reznor was realizing actual emotions (in theory; I have no proof he didn't just make it up). Johnny Cash could only relate to it, which is not bad in any way, but I just give it less weight. Going purely from a musical aspect, however, I like Cash's voice better, so would pick his version for only that reason.

For the heartbroken dubsteppers: Raise Your Weapon - Deadmau5

[Fedechiar]

How to Disappear Completely - Radiohead

Most Radiohead songs, really..."True love waits", "Fake plastic trees", "Street spirit (fade out)", "No surprises" (at first it sounds like a mellow, happy song, but then it hits you like a ton of bricks), "Optimistic", "There there", "The bends", "Killer cars"...And that's not even most of it

[bosonicyouth]

Feel compelled to stem the tide of NIN talk. I mean come on. Let's start with a live performance
Nina Simone - Feelings

and some recordings, probably too many but oh well
Antony and the Johnsons - Hope There's Someone
Sibylle Baier - Tonight
Joni Mitchell - Blue
Elliott Smith - New Disaster or, well, anything really
Marissa Nadler - Famous Blue Raincoat (Leonard Cohen)
Billy Bragg - Levi Stubbs' Tears
Paul Kelly - How To Make Gravy
Archers of Loaf - Perfect Time

and for the sheer awkwardness
The Gothic Archies - Smile! No-one Cares How You Feel on Good Day Atlanta

Party!

[cjmcjmcjmcjm]

Eleanor Rigby

[dshizzle]

Winter Winds - Mumford And Sons

[Jesse]

A Simple Process of Elimination, by Aereogramme

Makes me cry everytime, especially that end.

[upandcomer]

Falls Apart - Hurt

[3fj]

So many off of the Alchemy Index (except fire, though I guess that makes thematic sense)
Thrice - Digging My Own Grave

And so many Placebo songs, but this one always got me
Placebo - A Song to Say Goodbye

And if we're talking songs that tell a story:
He Is Legend - The Widow of Magnolia
Kaizers Orchestra - Bris
Kaizers Orchestra - Hjerteknuser

[theGoldenCalf;]

Roger Waters - It's a miracle

My Friend the Chocolate Cake - Can't find love

Eddie Vedder - Long night

[freezeblade]

Links are blocked at work, but I'm sure some of these are on youtube

GSY!BE - Dead Flag Blues
The Mars Volta - Televators
Zero 7 - the Road
Agalloch - The Hawthorne Passage
Kings of Convenience - Summer on the West Hill
Sol Invictus - The Edge Beckons
Venetian Snares - Colorless
SoulSavers - Revival
Ulver - Porn Pieces or the Scars of Cold Kisses

Off the top of my head. Of paticular note is the Sol Invictus track, gives me chills every time.

[Mikeski]

The also-rans:

Tirill - Vendela
VAST- The Nile's Edge
Porcupine Tree - Heart Attack in a Layby

The runners-up:

Pain of Salvation - Undertow
Tori Amos - Winter

And the songs in my collection guaranteed to produce a single, manly tear*:

Loreena McKennitt - The Highwayman (live version from the Paris & Toronto disc)
Marillion - Brave (yeah, it's a concept album. If I need to pick out particular parts, Standing in the Swing, The Last of You, Falling from the Moon. For extra sad, listen to the "sad ending" on the bonus disc, rather than the normal album's "upbeat" final song. And skip over Paper Lies either way.)
Ritsuko Okazaki - Sweet Dreams (not the Eurythmics' song. Knowing that she ended an album called Life is Lovely with a lullaby singing "...and sweet dreams.", and then she died of cancer...)

* - additional tears optional.

[UniqueScreenname]

Young Guns - Stitches

[Rium]

Cloud Cult – When Water Comes To Life

[SodoffBaldrick]

Henryk Górecki - Symphony Nº3. Truly wonderful music.
I can't link directly as it's flagged as spam, but add this to youtube and you'll get the music - /watch?v=ZVITZUQ_uIU

[pkcommando]

Can't do a link to it while at work, but:

Amanda Palmer - The Bed Song

[Suzaku]

YMMV

Jackie Oates - IOU
Wendy Matthews - The Day You Went Away
Alan Jackson - Sissy's Song
Rufus Wainwright - Hallelujah
Onitsuka Chihiro (鬼束ちひろ) - Arrow of Pain
Eric Bogle - The Green Fields of France
Luke Kelly - The Unquiet Grave

[CesarioRose]

I'm honestly pretty surprised no one has mentioned any Portishead song ever.
Western eyes, Sour Times, Roads, and Strangers directly come to mind.

Massive Attack has some great ones; Unfinished Sympathy, Protection, Black Milk/Black Melt, and Live With Me directly come to mind as distinctively sad for their own reasons. (Live with me's video, which I can't link to, but you should motivate your self to go watch it, is especially depressing.)

Trent's or Cash's rendition of Hurt is a newer classic.

Tricky's Ghetto Stars is polarizing, and socially dogmatic.

2econd Class Citizen - A World Without deals with some sad political topics.