Saddest Song in all Genres of Music?

Two that come to mind for me:

"It's Over" By Roy Orbison

"The End of the Rainbow" By Richard Thompson

Sylvia's Mother

Brick is also very sad

Johnny Cash's cover of "Hurt" by Nine Inch Nails and the associated video is pretty sad. He recorded it after his wife died and right before he died.

Oh Danny boy, the pipes, the pipes are calling

From glen to glen, and down the mountain side

The summer's gone, and all the flowers are dying

'Tis you, 'tis you must go and I must bide.

But come ye back when summer's in the meadow

Or when the valley's hushed and white with snow

'Tis I'll be here in sunshine or in shadow

Oh Danny boy, oh Danny boy, I love you so.

And if you come, when all the flowers are dying

And I am dead, as dead I well may be

You'll come and find the place where I am lying

And kneel and say an "Ave" there for me.

And I shall hear, tho' soft you tread above me

And all my dreams will warm and sweeter be

If you'll not fail to tell me that you love me

I'll simply sleep in peace until you come to me.

I'll simply sleep in peace until you come to me.

Johnny We Hardly Knew Ye (music: slower, earlier version of 'When Johnny Comes Marching Home').

Tim McGraw's "Don't take the girl."

Chiseled In Stone- Vern Gosdin

For me, the song that always comes to mind first is "Eleanor Rigby." Another, expressing similar themes, is "Dock of the Bay," although I find "Eleanor Rigby" to be more poignant. Both songs are among my favorites.

Henryk Gorecki's "Symphony of Sorrowful Songs" is pretty damn sad.

sunday mornin comin down

Easy, "Sad Song" off of Lou Reed's album Berlin. "The Kids" and "The Bed" off of the same album are just as dark.

Eric Clapton's song about his son after he died. I don't know the name but it goes; "Would you know my name, if I saw you in heaven."

Suicidal Thoughts - Notorious B.I.G.

Somebodys Gotta Die - Notorious B.I.G.*

Miss U - Notorious B.I.G.

* Sounds like another "ima shoot yo ass" gangsta song but the end really is like...whoa.

Alone Again (Naturally) - Gilbert O'Sullivan. Karma Police - Radiohead.

Copa Cabana- Barry Manilow

That's "Tears in Heaven" - and I agree

Good Die Young - D12, if youve lost a close friend or family member you can relate to this song big time. the only rap song i like.

"Best Man's Fall," by Trash Can Sinatras. Stupid band name, singlularly good song.

"The Nothing Song" by Sigur Ros.

I'm with you on Brick. I'm told that the song is exactly what it feels like to have had an abortion. I'm very grateful that I don't know.

"Iowa" by Dar Williams

"Space Dog," by Tori Amos

A couple of candidates outside of the Rock/pop genre

Komm, süßer Tod ("Come Sweet Death") - Bach (no lyrics at all)

"The Band Played Waltzing Matilda" - Eric Bogle, Lyrics here:

http://www.fortunecity.com/tinpan/parton/2/matilda.html

Liam Clancy does a great cover of this song.