‘Feb.14’ by Drive by Truckers
That’s Drive-By Truckers, girl! And the song would be World of Hurt. 
Sebadoh - Willing to Wait
Rilo Kiley - Science Vs Romance
Rachel Yamagata - Duet
Oh, lover, I’m old
You’ll be out there and be thinking just of me
And I will find you down the road
We’ll return back home to where we’re meant to be
Evermore by Neil Diamond. Came out as I was about to go through a divorce. Probably didn’t help that I immediately learned how to play it on guitar too.
From the same album: Windsurfer. “She told him no, no, never, no.”
‘The Man That Got Away’ sung by Judy Garland.
‘One Less Bell to Answer’ sung by the Fifth Dimension
‘Since I Fell For You’ sung by Lenny Welch.
There. There is the vast bulk of my romantic history, in song, right there.
Just One Smile by Blood Sweat and Tears.
My first girlfriend was in high school, and I was convinced, in that high school way, that we’d spend the rest of our lives together. She was a year behind me in school, but I skipped two years after college, in part so that she and I could go to the same school.
Some time after I graduated, things got distant between us. One afternoon I went over to her house, and she and I worked on arrangements for a song, Killkelly Ireland, she singing and playing guitar, and I on the violin.
After we’d worked on the song for an hour or so, she sat next to me on the sofa and very gently broke up with me.
That song is forever linked to that moment, and I’ve always thought that’s why I find it so sad; but the first comment on that Youtube video says,
Roxy Music’s “Oh Yeah” got a lot of play after my first marriage fell apart.
Far Behind by Jason and the Scorchers.
It’s not the deepest or most eloquent song ever written, but the first time I heard it I had just been through the most devastating breakup of my life. Between the lyrics and Jason’s mournful wailing, I felt as if this song had been created specifically to document my emotions at that particular moment.
Oh god. I just listened to that song again, and I’m about to break down sobbing.
The Boys of Summer. I keep memories of a long-gone girl in my head, like old movies endlessly replayed, too. (But I don’t have a Dead sticker on my car).
The Heart of the Matter. I think Don Henly is my separated twin, he writes songs that really hit me in the heart.
Suite: Judy Blue Eyes by CSN/CSNY. And as the heartbreak was happening as (and because) my own life was falling apart, the opening lines spoke my truth:
It’s getting to the point where I’m no fun anymore
I am sorry
Sometimes it hurts so badly I must cry out loud
I am lonely
All too suddenly, I had nothing to offer her but my own need and a cry of desperation:
Change my life, make it right, be my lady
When you dive into the water to try to save someone that’s drowning, you’re likely to get dragged under as well. She had enough of a clue to not try to rescue me.
February 1972. What a motherfucker it was. Amazing how you can still feel every bit of it, most of a lifetime later.
Good choice. I love the descending sequence of “My Days Are Numbered,” “Without Her,” and “Just One Smile” that finished up that side of the LP, back in the days of LPs.
The Hanks do sad songs very well.
Looks Like Rain…The Grateful Dead
But it’s alright cause I love you, and that’s not going to change.
Run me around and make me hurt again and again.
But I’ll still sing you love songs, written in the letter of your name.
The rain is gonna come, oh it surely looks like rain.
I don’t know where I’ve read it, but someone once said that “If You See Her, Say Hello” is the saddest love song of all time, and whoever it was, he/she was right.
I’ve known and loved “Blood On The Tracks” for a few years before, but all the pain, the hurt, desperation and anger that is expressed on this album only really made sense after my first real love broke up with me. That was a long time ago, but I still love to listen to it very much, it’s one of Dylan’s greatest albums, and every time I do I’m still a bit hurting. But it’s also cathartic.
Another Roxy Music suggestion:
- but really lost love was almost Ferry’s go to subject matter. There are quite a few others to choose from.
j
‘Catfish Bates’ by Don Williams
If the Phone Doesn’t Ring, It’s Me - Jimmy Buffett
That also appears on Dusty in Memphis. Which has a ton of heartbreaking songs.