What Is The Saddest/Depressing Song Ever?

Dance with the Devil by Breaking Benjamin

Happy birthday by Flipsyde

I don't love you by My Chemical Romance

Counting Crows - long December?

Jackson Browne - for a dancer

Interpol- a time to be so small

Adam's Song is a far more depressing song by blink 182 than I miss you.

About half of Nick Drake's songs are like musical downers.

James Taylor's Fire and Rain should be on this list.

Dave Wilcox's Eye of the Hurricane.

Also, lots of Ben Fold's songs: depressed, brick, etc.

Nilsson You're Breakin' my Heart

http://www.youtube.com/watch?v=02lXLiFsRtE

Gillian Welch - Annabelle

http://www.youtube.com/watch?v=ceDxO50GVes

Gillian Welch's entire album entitled "Hell Among the Yearlings". That title paints a pretty pictures.

The River by Bruce Springsteen

"Then I got Mary pregnant

and man that was all she wrote

And for my nineteenth birthday I got a union card and a wedding coat

We went down to the courthouse

and the judge put it all to rest

No wedding day smiles no walk down the aisle

No flowers no wedding dress"

Tears in Heaven by Clapton is very depressing, especially hearing the regret in Clapton's voice as he is tormented by the fact that he pushed his own infant son out a window in order to gain "Street Cred" amongst the blues community. A modern-day Raskolnikov, who sold his soul at the crossroads a la Robert Johnson, in his own special way.

R4Shot

Empire State of Mind.

I'm depressed that such a piece of crap can become such a worldwide hit.

Pearl Jam cover of "Last Kiss"

2:25 is elite. Not world class but elite.

How Soon is Now by the Smiths

I am the son

And the heir

Of a shyness that is criminally vulgar

I am the son and heir

Of nothing in particular

You shut your mouth

How can you say

I go about things the wrong way

I am Human and I need to be loved

Just like everybody else does

There's a club, if you'd like to go

You could meet someone who really loves you

So you go, and you stand on your own

And you leave on your own

And you go home

And you cry

And you want to die

When you say it's gonna happen now,

When exactly do you mean?

See I've already waited too long

And all my hope is gone

David Bromberg - Sammy's Song

http://www.youtube.com/watch?v=3AcPWNYwjj4

Another vote for Johnny Cash's version of 'Hurt'.

Also, 'Waco Moon' by Todd Snider.

to a husband at war - i hate myself

a perfect sonnet - bright eyes

miss misery - elliott smith

steps ascending - thursday