Recommend Unbelievably Sad Music

[Rushmore]

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Portishead is the band name, if that helps you.

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I thought I had everything they'd done. Never heard of "Drive."

The only truly "sad" Portishead song I can think of is "Undenied."

Anyway...."Drive?" Huh?

[ilya]

Well Leonard Cohen if you can stand his ridiculousness has some great sad songs. "The dealer," for example.
I'm sure you know Billie Holliday & Edith Piaf. If you have any French I'd recommend George Brassens. If you have any Russian & actually even if you don't, I'd really recommmend Vladimir Vysotsky (http://www.kulichki.com/vv/eng/), Bulat Oku(d)jawa, Novella Matveeva, & Galich.
Also early blues & jazz...Robert Johnson, Skip James, Armstrong's Hot Fives recordings.
Early Jay-Z.
Wilco, Flaming Lips, Violent Femmes, Neutral Milk Hotel, Moldy Peaches, decemberists...... wow I love sad music.

[diebitter]

The River - Springsteen

but you're bound to know that one...

[Rushmore]

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Paris Match - Style council
It's a very deep sea - Style Council

you ain't ever heard them ones, I bet

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This is true.

And while I am skeptical, I am resolved to try any and all reasonable recommendations made here (read: no, I will not "just give Journey a fair listen"), so I will try it.

[ilya]

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Portishead


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hell yeah. Portishead is awesome mopey music.

My Immortal - Evanessence (badly misspelled I believe)

[ilya]

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(read: no, I will not "just give Journey a fair listen")

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good man.

[Eihli]

Albinono's Adagio for strings.

[imported_anacardo]

Lotta good suggestions here. I'd like to put in a bonus good word for the Decembrists, particularly "Picaresque."

Now. This is gonna sound weird, but - a good bit of the soundtrack to Ken Burns' The Civil War absolutely brings me to my knees. And I'm not a weepy guy.

Haven't seen a mention of Patty Griffin yet. Her cover of Springsteen's "Stolen Car" is one of the most haunting things I've ever heard.

[whiskeytown]

Kate Rusby - she has the most beautiful and melochany songs in the world -

Try the album 10 and then The Girl Who Couldn't Fly - there are a few happy tracks but a lot of them have this sad loneliness to them - esp. sleepless sailor.

RB