[bushbison]

...oh yeah, and "Philadelphia" by Neil Young....

[Brian Albin]

Does anyone remember "Giddyup Go" by Red Sovine?
That was always a weeper for me.  Although I have not heard it since I was a teenager in the seventies, so it may seem different if I were to hear it again today. 
I think it was the way he delivered it as much as anything else that made it seem so sad.

[genjamon]

I agree with many of the posts thus far.  Of course, many of the Love Songs triple volume compilation by Stephen Merritt are rather sad.  One that sticks out is Epitaph for My Heart.

How about One By One off the Mermaid Avenue discs by Billy Bragg & Wilco?

[AB]

"Danny Boy"

Sung at my da's funeral and it'll be sung at mine.

That makes it the saddest song ever.

http://www.youtube.com/watch?v=Nzd6mbfp6rs
Or...
http://www.youtube.com/watch?v=81JG7Notka4

[cruz123]

I think I have everyone beat.

"Mary of the Wild Moor"

Was on one cold winter's night
And the wind blew across the wild moor
Poor Mary came wand'ring with a child in her arms
And she stopped at her own father's door.
Oh, father, oh father, she cried
Come down and open the door
Or this child in my arms, will perish and die
From the winds that blow across the wild moor.

Oh why did I leave this fair spot
Where once I was happy and free
This wide world to roam, with no friends or no home
And no one to have pity on me.

But the father was deaf to her cry
Not the sound of her voice, did he hear
For the watch dogs did howl and the village bells tolled
And the winds blew across the wild moor.

Oh, how the old man must have felt
When he opened the door, the next morn'
And found Mary dead, but the child still alive
Clasped close in it's dead mother's arms.
In anguish, he pulled his gray hair
And the tears, down his cheeks, they did pour
When he saw how that night, they had perished and died

From the winds that blow across the wild moor.
The old man, his life, pined away
And the child, to it's mother, went soon
And no one they say, lives there to this day
And the old house, to ruin, has gone.

But the villagers point out the spot
And the willows droop over the door
Where poor mary died, once a sweet village bride
From the winds that blow across the wild moor.

[jimdgoulding]

A very sad one, indeed.

[mdfoy]

Strange Fruit, Billie Holiday

[gerchin]

A completely different definition of "sad", but those who have been there will understand:  "Paint it Black"; Stones.

[amadeus916]

It really depends on my mood, but I would be able to throw a few various Elliott Smith songs into this catergory. His music is weird...The same song can either make me really sad, or really just ok with the world. All depends on the day. A few that could get me there...

- A Fond Farewell
- Happiness
- Not Half Right

Epic!

[beachbum]

OTIS REDDING
Fa-Fa-Fa-Fa-Fa (Sad Song)

Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa

I keep singing them sad sad songs, ya all
Sad songs is all I know
I keep singing them sad sad songs, ya all Sad songs is all I know

It has a sweet melody tonight
Anybody can sing it any old time
What in your heart puts you in a groove
And when you sing this song
It'll make youre whole body move

Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa
Your turn
I'll turn Your turn, now

All my life I've been singing these sad songs
Trying to get my message to you
But this is the only song [y'ALL] I can sing
And when I get to singing my message to you

It goes

Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa
Your turn

Its a lovely song Its just alive
It tells a story
You've got to get your message
A strong message I'm worried alive
I'm worried alive [Watch me]

Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa
Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa
Your turn
Everybodys turn
Everybodys turn Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa
One more time
Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa-Fa Worried alive
My man Otis the best soul singer ever hands down.

[jimdgoulding]

Heart Like A Wheel-  Kate and Anna McGarrigle (out of print, I think).  Linda Ronstadt did a cover of this on one of her albums.  Anna wrote it.  I got it.  Good for me. 

[craig223]

Taxi - Harry Chapin, two people who had love and gave it up to chase dreams that ended badly.

Taps or Amazing Grace at a funeral tear me up every time

Or this little poem said over the casket of a friend who died way too young:

May the road rise up to meet you.
May the wind be always at your back.
May the sun shine warm upon your face;
the rains fall soft upon your fields and until we meet again,
may God hold you in the palm of His hand.

[raov1]

There was a movie about this subject on the IMF channel a few months back. I believe it was called "The saddest song in the world"
 

[ratso]

There was a movie about this subject on the IMF channel a few months back. I believe it was called "The saddest song in the world"
 

haha

"he's not dead; he's just very very sad"

[raov1]

Uuh? 

[orthobiz]

Harry Nilsson
"Together" from Aerial Ballet (HIGHLY recommended)
Goes through the relationship from beginning to end with typical
wonderful Nilsson lyrical twists.

Life isn't easy when two are divided and one has decided
To bring down the curtain, and one thing's for certain...
There's nothing to keep them...together

How does it happen, that two can be tender
And one be the lender of love and emotion
That covered the ocean of sadness that kept them...together

Love when it's started is easy to measure
Each day was a pleasure each night an adventure
Each morning was something that has to be shared...together

Love when it's growing is full of surprises
His temperature rises from higher to higher
Then turns into fire which has to be shared...together

Then came the sadness which follows the laughter
Which shortly thereafter the dream had exploded
The promise was broken now few words are spoken...together

(Instrumental break of French horn and trumpet desperately
entwined yet apart...)

Life isn't easy when two are divided and one has decided
To bring down the curtain, and one thing's for certain...
There's nothing to keep them...together

Paul

[ratso]

Uuh? 

you know the scene where the guy in the black veil..




never mind.

[boead]

I know what I said
Was heat of the moment
But theres a little truth in between the words we've spoken
Its a little late now to fix the heart thats broken
Please dont ask me where i'm going
Cuz I dont know
No I dont know anymore

It used to feel like heaven
Used to feel like may
I used to hear those violins playing our strings like a symphony
Now they've gone away
Nobody wants to face the truth
But you wont believe what love can do
Till it happens to you
Till it happens to you

Went to the old flat
Guess I was trying to turn the clock back
How come that nothing feels the same now when im with you
We used to stay up all night in the kitchen
When our love was new
Oooh love im a fool to believe in you
Cuz I dont know
No I dont know
Anymore

It used to feel like heaven
It used to feel like may
I used to hear those violins playing our strings like a symphony
Now they've gone away
Nobody wants to know the truth
Until their hearts broken
Dont you dare tell them
What you think to do
Till they get over
You can only learn these things
From experience
When you get older
I just wish that someone would have told me
Till it happpens to you
Till it happens to you
Till it happens to you

[martinr]

The Hand Song -
Nickel Creek

[raov1]

Uuh? 

you know the scene where the guy in the black veil..


never mind.

    I thought it might be in those lines. I never got to see the movie, just bits and pieces. Damn "America's next top model" and 16 y/olds.