the album leaf- streamside
death cab for cutie- brothers on a hotel bed
the weepies- the world spins madly on
the microphones- i want wind to blow
ingrid michaelson- keep breathing
margot and the nuclear so and so's- light on a hill

and anything by glen hansard :]

One of the most depressing songs I've heard is "A Rose For Emily"

The opening lyrics are:

It gets sadder from there.

He's a sad bastard alright.

Def, i recently came upon this list. I'm of no opinion on it but I thought it fit the thread.

For the lonely: 150 songs for sobbing on Valentine's Day | Pop & Hiss | Los Angeles Times

located here

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Saddest song I have ever heard...

"For My Fallen Bride", by, ironically, a band called "My Dying Bride"...

But its the most heart wrenching description I've heard of holding the one you love while they slip away from this world... I'm no big crying guy, but man, this song gets me all choked up every time...

Here Comes the Flood by Peter Gabriel has the same effect on me when I hear the version of it with just him and a piano... stunning, beautifulo, incredibly depressing... :-)

This song is based on a short story by William Faulkner that goes by the same name.....Really good/sad/shocking story...if you haven't read it already, you should.

Eric Clapton's Tears in Heaven while very sad doesn't quite evoke the same kind of sadness of some of the saddest songs I know, but the story behind it is pretty awful. The song is about his son who fell out of a 53rd story window at the age of four .. The song is not all gloom because it has a of hopeful part to it that makes it feel even more real, I think.

Eric stopped playing it after he came over the loss. Awful tragedy and an amazing song ..

Any song off of Beck's "Sea Change"! Just a sad album overall!!!

The saddest thing I ever did see
Was a woodpecker peckin' at a plasitc tree.
He looks at me, and "Friend," says he,
"Things ain't sweet as they used to be."

-Shel Silverstein