I forgot about Sinatra singing One For My Baby (And One More For The Road) . A great song for when the affair is over and you just want to drink it all away. When that special someone has left you and you don’t know if you can go on, get Frank Sinatra Sings for Only the Lonely and you’ll know that life does go on. Of course it will be going on without you and she’ll be happier with someone else and you might as well just have another drink before you go back to your empty bedroom and stick your head in a noose.
I never could quite handle “You Don’t Know Me”. The prelude shuts me up, then Ray’s first four lines,
tear (in both n=meanings of the word) me up, because I know what’s coming. But I listen anyway.
The song is so damn beautiful!
… Or anything else on that album, really – “Tangled Up in Blue” and “Shelter from the Storm” have got to be right up there, but I think it’s “If You See Her, Say Hello” that always gets me:
No one has mentioned Kris Kristofferson? For the Good Times always makes a gray day more miserable; so does Casey’s Last Ride or even Help me Make It Through the Night…(Lord, it’s sad to be alone…)
And Linda Ronstadt’s version of A long Long Time.
I just remembered a really heartbreaking song:
The River by Bruce Springsteen
Love is crushed by the real world. It starts out nice:
*Me and Mary we met in high school when she was just seventeen
We’d ride out of that valley down to where the fields were green
We’d go down to the river
And into the river we’d dive
Oh down to the river we’d ride*
…but then Mary gets pregnant, Bruce gets a construction job and the love fades away:
There is a song by James Blunt - it’s not very old - but each time I hear it I think that it is so sad:
Did I disappoint you or let you down?
Should I be feeling guilty or let the judges frown?
'Cause I saw the end before we’d begun,
Yes I saw you were blinded and I knew I had won.
The lyrics are fairly simplistic, but “The Ghost of You” by My Chemical Romance always gets to me. There’s just something about how Gerard Way’s voice and the music come together that fills me with an unspeakable melancholy for lost loved ones. The video just makes it all the worse. But, man, is it beautiful. One of my favorite songs of all time.
Whoa! That’s going on my ‘shitfaced, melancholy and unrequited’ playlist.
I’m going to nominate “Where’ve You Been?” by Kathy Mattea, because it makes me cry damned near every time I listen to it, and it is a love song about two old people.
How about “Baby, Now That I’ve Found You” by Alison Krause - it seems like a nice little love song, but it’s about someone who won’t let go after they’ve been rejected?
Some others -
“I Honestly Love You” by Olivia Newton John
"I’ve Been Loving You Too Long (To Stop Now) by Otis Redding
“Love Hurts” by Nazareth
“My Heart Can’t Tell You No” by Rod Stewart
“My Heart Will Go On” by Celine Dion (I know it’s very trendy to hate everthing about “Titanic,” but this song moved me deeply for a long time after seeing that movie)
Here’s some for the Canadians - “Janine” by Trooper, “Every Time I See Your Picture I Cry” by Luba, and “Hurts To Be In Love” by Gino Vanelli.
And, of course, “Achey Breakey Heart” by Billy Ray Cyrus. 
A Summer Song by Chad & Jeremy makes me snivel every time I hear it.
It Was A Very Good Year by Frank Sinatra always sounds so melancholy, as though it were a ghost singing the song. Perhaps not specifically a love song, but maybe a love song to a life gone by…
“Tangled Up In Blue” by Bob Dylan gets to me–they’re both so broken.
When I was in college, we’d put this on the stereo and everyone walking down the hallway within earshot would suddenly stop and look down at their feet. A real knife-twister.
A Good Year for the Roses is, without a doubt, the saddest love song you’ll ever here. Again, the lyrics don’t do it the full justice - its as much about Costello’s delivery as it is about the story (an average guy realising that his wife no longer loves him).
My personal saddest love song is Sting’s Ghost Story, but that’s because the exact situation and realisation it described is something i personally experienced. There’s nothing that can hit harder emotionally than realising too late that, through your own stupidity and inability to acknowledge the way you feel, you have tricked yourself out of the one person you ever truly loved.
That’s the song I came to mention.
Right after the last line you quoted comes my favorite Springsteen line (and THAT is saying something):
Yeah, I’ve been there. Been there real hard.
Another brilliant ‘love crushed by the real world’ song is *‘Gladstone Pier’ * by the Australian band Redgum. The decline and fall from:
Peter was a sailor
Swarthy lean and proud
He could take a schooner through a big sea swell
Aloof in the mainland crowd
Is as inevitable as it is heartrending.
The whole thing (plus other songs by John Schuman) can be found here
Isn’t there a song where they pretty much follow the life of a couple all the way thru to a retirement home?
On a total aside, that line will stay with me for my whole life. Back in the mists of time, the Oxford entrance exam had a General Paper that was complusory (for my subject at least). It was a quasi-philosophical type essay exam, taken by a bunch of 17 year olds so you can imagine the trite crap that was written.
Generally it was a good exercise - a lot of the questions were quotes, with ‘discuss’ after them. Sorts of questions like “‘Science has nothing to be ashamed of, not even the ruins of Nagasaki.’ (J. Bronowski). Is this an acceptable view of the interplay between science and morality?”
Anyway, its a very stressful exam period for a 17 year old, especially because ti took place at a time when none of my friends were taking their exams (just before Christmas). So I sat down, opened up the paper, and started laughing my ass off. There, in front of me, was the following:
“‘Is a dream a lie if it don’t come true, or is it something worse?’ (B. Springsteen). To what extend does Mr. Springsteen’s comment reflect an accurate description of dreams?”
We now return you to your regular thread…
Ugh! Nothing depresses me more (even 1 years later, now) than MaryChapin-Carpenter’s “Only a Dream” … the divorce theme for my 1st marriage…
The day you left home you got an early start
I watched your car back out in the dark
I opened the door to your room down the hall
I turned on the light , And all that I saw
Was a bed and a desk and couple of tacks
No sign of someone who expects to be back
It must have been one hell of a suitcase you packed
I second garius’ on “Ghost Story,” the fact that the melody is almost cheerful and upbeat at the end make the lyrics even MORE sad somehow.
But I’ve gotta vote for Blue October’s “Hate Me,” that song KILLS me, I imagine an ex of mine saying something similar. (He didn’t, but sometimes you wanna pretend they’re out there somewhere kicking themselves, ya know?)
"And with a sad heart I say bye to you and wave
Kicking shadows on the street for every mistake that I had made
And like a baby boy I never was a man
Until I saw your blue eyes cry and I held your face in my hand
And then I fell down yelling “Make it go away!”
Just make a smile come back and shine just like it used to be
And then she whispered “How can you do this to me?”
Beautiful lyrics, and such an anguished sound. Totally teared up the first couple times I heard it.
Romeo and Juliet is a great, sad song.
I’d like to nominate the album “The Forgotten Arm” by Aimee Mann. The entire album is about a failed love story, and Aimee Mann can indeed write a hell of a song.
“Untitled” by Domestic Problems, an indie band based out of Grand Rapids, MI, is one of my favorite sad songs. It’s about unrequited love. An acoustic guitar provides the rhythm guitar line and an electric mandolin provides the intrumental part of the melody. The song is currently hosted on their MySpace page .
I can tell you the stories
Battles never won
Of people standing blindly
Out of reach of the sun