Starry, starry night
Portraits hung in empty halls
Frame-less heads on nameless walls
With eyes that watch the world and can’t forget
'll be seeing you
In all the old familiar places
That this heart of mine embraces
All day and through
I also love the second and last stanzas from that song:
I know a woman; became a wife
These are the very words she uses to describe her life
She said a good day ain’t got no rain
She said a bad day is when I lie in bed
And think of things that might have been.
If you haven’t heard it, for some reason I find the demo to be even sadder than the final version.
Another Paul Simon nomination, from one of my favorite songs of his (and just all time favorite songs, as well):
Kathy, I’m lost, I said, though I knew she was sleeping
I’m empty and aching and I don’t know why
Counting the cars on the New Jersey turnpike
They’ve all come to look for America, all come to look for America.
I also love “I Am a Rock” - the last two lines sum it up:
And a rock feels no pain;
And an island never cries.
My final Paul Simon one, “Graceland” - the stanza that stands out to me is:
She comes back to tell me she’s gone
As if I didn’t know that
As if I didn’t know my own bed.
As if I’d never noticed
The way she brushed her hair from her forehead.
Huh. I started out intending to do one of his songs, and ended up with four. I guess he does sad really well. 
OK, last ones - so many Leonard Cohen songs, especially the very early ones, are achingly sad, but the two that stand out to me are “Famous Blue Raincoat” and “That’s No Way to Say Goodbye”. The latter sounds like a “we’re-so-happy-together” love song, until you realize that she left him, and the former is just . . . depressing beyond all reasonable bounds, with some mystery thrown in.
Most of mine have been mentioned, but I’ll add Send In the Clownssung by Judy Collins. Just hearing the oboe at the beginning immediately puts me in a sad place.
Also How To Save a Life, by The Fray:
Where did I go wrong? I lost a friend
Somewhere along in the bitterness
And I would have stayed up with you all night
Had I known how to save a life
When this song came out, my daughter’s close friend, such a sweet young soul, had just committed suicide. I couldn’t even listen to the entire song for about a year, and it still makes me cry.
correct… more detail, should anyone care
What about “Richard Cory”?
He freely gave to charity, he had the common touch,
And they were grateful for his patronage and thanked him very much,
So my mind was filled with wonder when the evening headlines read:
“Richard Cory went home last night and put a bullet through his head.”
Or “A Most Peculiar Man”:
To his silent world and his tiny room;
And Mrs. Riordan says he has a brother somewhere
Who should be notified soon.
And all the people said, “What a shame that he’s dead,
But wasn’t he a most peculiar man?”
Paul Simon (with and without Garfunkel) made some pretty depressing music. Good, but depressing.
And she said losing love
Is like a window in your heart
Everybody sees you’re blown apart
Everybody sees the wind blow.
I wanted to use that one, too. I slipped some of it into a poem I wrote about writing poems as an example of one that gives you an immediate emotional reaction.
A reminder to everybody: please don’t quote more than five lines from any one song unless it’s in the public domain. Thank you.
Tom Paxton’s Born on the Fourth of July:
Now I wheel myself down to the crossroads of town,
To see the young girls and their lovers.
And my mind is afire, it’s alive with desire,
Christ, I’d barely begun, now it’s over.
In my wheelchair for life, my mechanical wife,
I’m supposed to be cheerful and stoic.
I’m your old tried-and-true, Yankee Doodle to you,
Clean-cut, paralysed and heroic.
I was born on the Fourth of July.
No one more loyal than I.
When my country said so, I was ready to go
And I wish I’d been left there to die.
I think “when a bluegrass song starts” is enough to clue you in that somebody dies during the song.
[QUOTE=someone else]
Christmas Shoes.
[/quote]
:rolleyes:
The Waterboys: “The Whole of the Moon”
Still breaks me up a little. 
Reminds me of “First Christmas” by Stan Rogers. Not the absolute saddest song I can think of, but very melancholy.
Fire and Rain, James Taylor
Wreck of the Edmund Fitzgerald, Gordon Lightfoot
El Paso, Marty Robbins
The Gunners Dream - Pink Floyd
Each Small Candle - Roger Waters
Who By Fire - Leonard Cohen
I apologize if these were already posted.
I can’t listen to Ian Tyson’s “Barney” without breaking into tears.
Two from Slim Dusty
The Biggest Disappointment Written by Joy McKean(Dusty’s wife)
Turn Him Out In The Long Yard Written by Kelly Dixon
Came here to say this. And it’s a true story. Holy crap, can’t hear that without tearing up.
That’s certainly a frontrunner for me.
Back When We Were Beautiful reduces to me a puddly mess.
I am a huge Queen fan, and have always been moved to tears by These Are the Days of Our Lives. I cannot bear to watch the original video when Freddie Mercury was so thin, but I do like this versionwhen Queen performed it after Freddie’s death.
It’s both heartbreaking and heartwarming to me when the picture of a young Freddie appears and the audience cheers.
Sorry the video quality isn’t up to par, but I can no longer access the official version of this performance.
Look on Down from the Bridge by Mazzy Star