Hard to pick just one, but I’ll go with “Salome” by Old 97’s if you are taking it hard.
Salome, uncross your heart
I know what goes on inside, it's over before it starts
Stay all night, yeah I'll wait right here
The full moon might work magic, girl but I won't disappear
And I'm tired of makin' friends and I'm tired of makin' time
And I'm sick to death of love and I'm sick to death of tryin'
And it's easier for you, oh it's easier for you
And it's easier for you, it's easier for you
Salome, untie my hands
Well I'll find another lady and you'll wreck another man
It's over now, yeah and so are we
My blood's turned to dirt, girl you broke every part of me
And I'm tired of makin' friends and I'm tired of makin' time
And I'm sick to death of love and I'm sick to death of tryin'
And it's easier for you, oh it's easier for you
And it's easier for you, oh it's easier
And I'm tired of makin' friends and I'm tired of makin' time
And I'm sick to death of love and I'm sick to death of tryin'
And it's easier for you, yeah it's easier for you
And it's easier for you, oh it's easier for you
I listen to lots of classic country so no shortage of hurting songs. I sometimes quiz my 16 year old on whether a song is hurtin’, drinkin’ or cheatin’. You have to understand the root cause.
The best post breakup recovery song has to be “Positively 4th Street” by Dylan.
Speaking of Dylan, I don’t think any song captures a strange relationship like Joan Baez “Diamonds and Rust”. If you have someone in your life who comes in and out of it as the years pass, that’s the song.