Don’t Think Twice, It’s Alright - Bob Dylan. It’s more about dumping someone else, though.
I second Melandry’s recommendation for Sea Change, by Beck. It’s a great break-up album.
If you’re going for the bitter, angry thing, try Aerosmith’s “What it Takes.”
If you’re going for the wallowing in misery thing, try Alison Krauss’s “It Doesn’t Matter” (not to be confused with her song “It Don’t Matter Now”). Ignore that it’s the wrong gender - that one is pure aching sorrow. Hide the razor blades first.
Other choices:
Many by Jeff Buckley - Last Goodbye, Forget Her, Hallelujah (his is the best version)
Gin Blossoms - Found Out About You
Chris Isaak - Wicked Game
Led Zeppelin - Your Time is Gonna Come
Soft Cell - Tainted Love
U2 - One
Jason Mraz - You and I Both (for the optimistic “getting over it” part)
“Slash Your Tires” by Luna. Indulge in some nice revenge fantasies!
“The End of the World” by the Pet Shop Boys. (Note: stay well away from “You Choose”.)
“Just Friends” - Rev. Billy C. Wirtz
“Joking” - Donnie Iris
(excerpt)
Remember when you looked at me and said how was it
Remember when you asked if I was satisfied
And I said you were the best I ever had
Remember when I said that this was just like heaven
Remember when I said that this was ecstacy
And I never knew how kinky you could be
I told you you were big league good
I told you I’d never leave babe
But I was joking
I hope you realize
Joking
Telling you those lies
J-j-j-joking
Talking out my head
Joking
Don’t believe a word I said
Cause I all I wanted was a little bit
“Love Stinks” by the J. Geils Band, of course;
“Sunshine (Go Away Today)” by Jonathan Edwards is a good sort of cathartic number.
Some more thoughtful ones:
“Lover, You Should Have Come Over” by Jeff Buckley;
“The Tailor of Aquitaine” by Jack Harris;
“Both Sides Now” by Joni Mitchell;
“Closing Time” by Leonard Cohen. Each of these ones helped me work through some of the feelings left over from my last breakup.
But what I think are especially helpful – at least for me – are the “screw you, World, I’m going to make it through no matter what you throw at me!” A few of those-type songs:
“You Can’t Always Get What You Want,” by the Rolling Stones
“Don’t Stop” by Fleetwood Mac
“Why Should I Worry?” by Billy Joel
“Kick in the Ass,” Moxy Fruvous.
Pretty much all of Derek and the Dominos (Clapton and various friends) “Layla and other Assorted Love Songs”, including “I Looked Away”, “It’s Too Late”, “Key To The Highway”, “Why Does Love Gotta Be So Sad”, “Bell Bottom Blues”, and especially “Rose Tree In The Garden”.
I’m not a Dylan fan paticularly, but “Tangled Up In Blue” is also a good one.
Hell, I think half the lyrics ever written are committed to some lost or unrequited love. How hard can it be to find something?
Stranger
Heard it in a Love Song - Marshall Tucker band
Hasn’t hit me yet - Blue Rodeo
Angry all the time - Bruce Robison
Never gonna fall in Love Again - Eric Carmen
Love Don’t Live Here Anymore - Rose Royce
and everything on the album Amplified Heart- by Everything but the Girl
Not exactly within your request parameters, but it does deal with the topic.
Breaking Up Is Hard To Do by Neil Sadaka. It’s one of those songs that suggests you wallow in self-pity, which, as we all know, is a key element of breaking up.
Are You Happy Now by Richard Shindell
Excerpt below
“It’s Too Late” Carole King
“Almost Hear You Sigh” by the Rolling Stones.
IMHO, the best breakup song, ever, is You’re Breakin’ My Heart by Harry Nilsson.
You’re breakin’ my heart
You’re tearin’ it apart
So f** you…*
Almost any track on Over by Peter Hammill.
Lyrics here, on his website
“On Tuesdays she used to do yoga
on Tuesday she went away”
Broken Hearts are for Assholes by Frank Zappa
“Being In Love Really Sucks” by Meryn Cadell
Our man Ben has broken up alot. Also see “Selfless, Cold and Composed” on the same album, and “Give Judy My Notice” on one of his solo EPs.
I second this album. It’s one of those albums where it makes you feel really depressed about your break up, but its a “good” depressed… if that makes sense.
Break Up To Make Up - The Stylistics
Love On the Rocks - Neil Diamond
Better Off Now by Will Hoge. He’s kinda lame, but I like this song.
Cowboy Mouth is great. Try Laughable for a bit of self-pity. Then go for Love Of My Life, and my personal favorite Better, which are both about getting over her.
I Feel Fine by Riddlin Kids is pretty good to.