Every Time You Go Outside I Hope It Rains by the Burch Sisters:
“I’m not gonna wish you all the best.
I hope you’ll be lonesome, stay worried and depressed
I think I’ve summed it up in this refrain,
Every time you go outside, I hope it rains.”
Some good songs by Dylan have already been mentioned. And of course The Breakup Song by Greg Kihn. But I like Watching You by Melisse Etheridge
If I can’t love you I don’t want to love you
If I can’t hold you I don’t want to be thinking of you
and if you don’t want me I don’t want to want you
and if you won’t see me I don’t know what to do
but I’ll keep watching you
'cause I gotta do something
John
There was some country song, Lesson in Leaving, I think it was called:
Somebody’s gonna give you a lesson in leavin’
Somebody’s gonna give you back what you’ve been givin’
and I hope that I’m around
To watch 'em knock you down.
I found it very satisfying.
Of course, entering my ex-boyfriend in an Ugly Dog contest also helped! 
Two Rolling Stones songs mentioned, and no one’s talked about Dead Flowers yet?
“And you can send me dead flowers every morning
Send me dead flowers by the mail
Send me dead flowers at my wedding
And I won’t forget to put roses on your grave.”
SlipKnot’s “Everything Ends”
<Macho man savage>Ooooh yeahhhhh!</macho man savage>
Kina–Girl from the gutter
Sing along now and feel the empowerment.
- For all the times you said you had my back,
for all the times you stabbed me there, for all the times you tried to hurt my pride and hold me down with bitterness and dispair.
Thngs are looking up for me now, it seems that Karma’s making its way around. It’s your turn now I won’t be held down no. Karma’s gonna visit you too. You’re gonna pay for all the things you put me through–I hope you do.
I hope your hell is filled with magazines. And on every page you see a big picture of me, and under every picture the caption will read–not bad for a girl from the gutter like me.*
I didn’t see this before. How about Last Goodbye?
Kiss me, please kiss me. Kiss me out of desire baby not consolation. You know it makes me so angry when I know inside. I’ll only make you cry. This is our last goodbye.
Weird Al Yankovich again. One More Minute
Well I heard that you’re leavin’
Gonna leave me far behind.
Since you found your brand new lover
you’ve decided that I’m not your kind.
So I pulled your name out of my Rolodex
And I tore all your pictures in two
And I burned down the malt shoppe where we used to go
just because it reminds me of you.
I have an “I Hate Men” playlist for such occasions (I also have an “I Like Men”). For the former, it has many songs mentioned. Also, “Thorn in my Side” by the Eurythmics.
Also, “Screw You” by Pat McCurdy (a Milwaukee-area singer)
You wanna know what I’ve been doing
Since you left me with a broken heart
I get the feeling that you’re hoping
That I’m still miserable, still torn apart
You wanna know what I’ve been up to
Since you walked out and turned me upside down
Well, I won’t lie to you
Chorus
I’ve been going out, having fun, making friends
Screw you
Going places, running wild, meeting people
It’s true
Doing things I couldn’t do
All those years I spent with you
Never thought forgetting you
Would be so easy
You only come back when you want to make sure
That you’re still in control
Now and then you have to let me know
That you own my heart and soul
And you don’t care what I’ve been doing
Since you’ve left me, I’ll tell you anyway
And I won’t lie to you
Chorus
One thing you can do for me:
Get out of my memory
I never thought that being free
Would feel so joyful
You say this is how our relationship ends
We can still be friends
I don’t believe I’ve ever heard
Such utter bullshit
Well, I’ve been going out, having fun, making friends
Screw you
Going places, running wild, meeting people
Screw you
Going out, getting drunk, having sex
Screw you
Going out, writing checks, using your bank card
Screw you
Going out, having fun, making friends
Screw you
The One I Love, REM. Something about the minimalism, the directness, the…the utter coldness, it just grabs me. No elaborate proclamations or ranting; the singer sounds like he barely even cares.
I Ain’t Missing You, John Waite. So much raw anger and bitterness. Way cool.
And one of mine:
Cup of coffee (Garbage), a sample:
You left behind some clothes
My belly summersaults
When I pick them off the floor
My friends all say they’re worried
I’m looking far too skinny
I stop returning all their calls
And no, of course, we can’t be friends
Not while I’m still so obsessed
I want to ask where I went wrong
But don’t say anything at all
"Bye Bye Love" - Everly Brothers
"Bed’s Too Big Without You" - The Police
"Tear Stained Eye" - Son Volt
"This Old Cowboy" - Marshall Tucker Band
"Valentine’s Day Is Over" - Billy Bragg
“In the hush before the heartbreak”- the Nields
“Arrow”- Cheryl Wheeler
“February”- Dar Williams
“Alone”, from Blues Traveler’s first album, the title of which escapes me. It’s absolutely perfect for making you feel even worse…
Heartbreaker - Pat Benatar
Treat Me Right - Pat Benatar
Invincible - Pat Benatar
No More I Love Yous - Annie Lennox
Don’t Ask Me Why - Eurythmics
You Hurt Me, And I Hate You - Eurythmics
What Have I Done To Deserve This - Pet Shop Boys
Love Don’t Live Here Anymore - Madonna
You’ll See - Madonna
Twist In My Sobriety - Tanita Tikaram
Fear - Sarah McLachlan
Adia - Sarah McLachlan
Black - Sarah McLachlan
Go To Hell - Nina Simone
To Hell With Love - Annie Ross
Wuthering Heights - Kate Bush
Doctor, Doctor - Thompson Twins
Nothing In Common - Thompson Twins
Why? - Bronski Beat
Don’t Leave Me This Way - Communards
I Will Survive - Cake
The Winner Takes It All - Abba
Love To Hate You - Erasure
Deeper Love - Aretha Franklin
Respect - Aretha Franklin
You Keep Me Hangin’ On - Kim Wilde
here are a couple of great ones that come to mind, i dont know if ive mentioned them before:
Last Goodbye - Jeff Buckley
It’s Harder Now that It’s Over - Ryan Adams
Walk Away - Ben Harper
The Breakup Song - Greg Kihn Band (this was already mentioned, but it was the first thing I thought of.)
These Boots Are Made For Walking - Nancy Sinatra
F.O.D. - Green Day
Now That You Are Gone - Mr. T Experience
Those 3 just crack me up, but if I wanted to do it a bit of wallowing first, I’d choose:
The World Has Turned And Left Me Here - Weezer
Two by Kate Bush, from The Red Shoes (1993):
“Moments of Pleasure”
- I think about us lying, lying on a beach somewhere. I think about us diving, diving off a rock into another moment.*
“You’re the One”
It’s alright, I’ll come by when you’re not in, and I’ll pick up all my things. Everything I have a bought with you, but that’s alright too. It’s just everything we do, we did together. And there’s a little piece of you in whatever. I’ve got everything I need. I have petrol in the car. I’ve got some money with me. There’s just one problem: You’re the only one I want.
They get me every time. The album came out a few days after I broke up with someone, and these songs brilliantly put it all into words and music. I believe she broke up with her longtime bass player and producer, Del Palmer, the year before.
- s.e.
I’ve also written my own share of breakup songs, many of which found their way into my second and third musicals. Quoting their lyrics would be kind of pointless given none of you can hear the music.