**“Hate Me” ** by Blue October
I have to block out thoughts of you so I don’t lose my head
They crawl in like a cockroach leaving babies in my bed
Dropping little reels of tape to remind me that I’m alone
Playing movies in my head that make a porno feel like home
I believe you meant George Jones’s delivery. 
He’ll Have To Go by Jim Reeves is a classic, and most singers don’t dare to try it. Ry Cooder did the song proud, with heartbreaking flourishes from Flaco Jimenez.
“Put your sweet lips a little closer to the phone,
And we’ll pretend that we’re together, all alone.
I’ll tell the man to turn the jukebox way down low,
And you can tell your friend there with you, he’ll have to go.”
John Hiatt has three contenders: Lipstick Sunset, The Back Of My Mind, and Icy Blue Heart. Emmylou Harris covered Icy Blue Heart, but even her heavenly voice could not improve on Hiatt’s glissando, singing, “to melt her icy blue heart.”
You want sad? The song is actually for his mother, who had died. (Gimme a minute) 
You can hear her worriedly checking up on him on his anawering machine at the beginning of the video. Look at his face in the video. He is truly tore up. The boy in the vid is him
I have to go for a drive after I watch it. Every time.
Do not watch this if you get depressed.
It is beautiful. I like most of their other stuff too.
I think the winner for saddest divorce song may go to (video clip) Why? by Annie Lennox.
This is the book I never read
These are the words I never said
This is the path I’ll never tread
These are the dreams I’ll dream instead
I think Annie’s beautiful voice has dropped just a little.
Man’s got a nose on him, don’t he? 
Sorry. We used to talk about that back in Bakersfield. Made it easier to not cry in front of our buddies, I think.
That’s one of those singers who made the girls dance a little closer at “The Blackboard”.
You did, though, have to be careful what girl you danced with. Anyone who understands country custom will know what that means.
Oops.
She is so…friggin…beautiful. Unusual.
Anyway, do you get a low volume on that video?
One song I came in here to mention was Dire Straits’ “Romeo & Juliet,” but one or two (maybe a dozen) seem to have beat me to it.
“Keep Me in Your Heart for awhile” by Warren Zevon. Possibly the saddest song I’ve ever heard, even without knowing the circumstances behind it. Knowing that it was his death that was what was going to keep him and his love apart made it even worse.
Showing my age, Lynyrd Skynyrd’s “Free Bird” still brings a, well, hint of moisture to my eyes.
Peace - DESK
Tom Waits’ I Hope That I Don’t Fall In Love With You. Damned missed opportunities.
John Hiatt’s saddest is The Way We Make a Broken Heart , a duet with Roseanne Cash, depending on how broad your definition of love song is. It’s a killer, and I love it.
Sample:
Oh, this is the way we make a broken heart
Lesson number one we’ve just begun
To hurt him so
And with lesson two I’ll long for you
When lights are low
And we get to lesson three
When he gets down on his knees
And begs me to stop at the door
Just before
He comes apart
-Lil
Just reading this thread requires some major happy music- LOUD- to keep an even keel.
Forever Autumn has already been mentioned; it’s even worse when the person being spoken of (“now you’re not here”) is dead.
Two for not letting them get away, but throwing them away:
Don’t Come Around Here No More , by Tom Petty and the Heartbreakers
You Were Always On My Mind , by…Bob Segar? Anyway, the Pet Shop Boys(!) techno(!!) cover causes such mental frission (in me) that I have to be careful around sharp objects.
I did an almost unconscious little ‘augh’ when I saw that one. Oh yeah.
More Than a Whisper, Nanci Griffith:
The Ship Song, Nick Cave and the Bad Seeds. (I actually first heard this one sung by Concrete Blonde, live in concert. It was amazingly powerful.)
A Case of You, Joni Mitchell. Naturally, I first listened to this song right after a bad breakup. The Tori Amos singin’ it version, actually. Talk about slit your wrists time.
For that Blue October song? Holy crap, I didn’t know he was singing about his mother. The song was sad before, and now it’s got me sobbing all over myself.
Not necessarily a romantic love song, but (shuddup, okay?) Into the West from the Return of the King soundtrack makes me bawl every. single. time.
Man, I’ve got to go wash my face. Augh.
I was going to say “For No One” by the Beatles, but then I noticed some Leonard Cohen songs mentioned here and those are far sadder.
Nah - Costello version for me. Probably helps that i’ve seen him do it live and there wasn’t a dry eye in the audience.
Willie Nelson. 
What makes that song even sadder is that it’s supposed to be about his Mom, and (if the video is any indication) his regret now that his Mom is dead.
ETA: Wiki link: Hate Me.
As much as the song comes up on these boards, I’m surprised no one has mentioned Ode to Billy Joe by Bobbie Gentry.
This was the first song I thought of when I read the thread title, and I’m surprised it took three pages before someone mentioned it. That song is just absolutely heart-breaking.