Karaoke party this weekend. Wife’s acquaintance is attending, still suffering the aftermath of a nasty breakup.
What good-to-great breakup songs or “I-dumped-that-man” songs can we try to talk her into singing?
The mother of all breakup songs, “I Will Survive.”
“Goodbye, Earl,” by the Dixie Chicks.
“Goodbye to You”, Scandal (but only if she’s a child of the early 80s 
)
Cry Me A River - Justin Timberlake
You Oughta Know - Alanis Morrissette
Go Your Own Way - Fleetwood Mac
Since U Been Gone - Kelly Clarkson
'Tear Stained Letter" by Richard Thompson.
“Don’t Think Twice” by Dylan is one by the breaker-upper.
Here You Come Again by Dolly Parton
Look Away by Chicago
How Do You Like Me Now by Toby Keith
So hey, won’t you play another Somebody-Done-Somebody-Wrong-Song
And make me feel at home while I miss my baby.
So play, play for me a sad melody, so sad that it makes everybody cry.
A real hurting song about love that’s gone wrong.
So I don’t have to cry all alone.
B J Thomas at his best.
The Supersuckers’ Pretty Fucked Up is a rocking good one!
http://www.youtube.com/watch?v=A0-F5EX3hHw
Song for the Dumped - Ben Folds Five
Unfortunately more from the perspective of a man, but still a classic breakup song IMHO.
Break Your Heart - Barenaked Ladies is pretty good too. Depends on the situation, tho.
Love Stinks, J. Giels Band
Harden My Heart by Quarterflash
What about “The Breakup Song” by Greg Kihn? The lyrics are gender-neutral.
She’d need to alter the lyrics a bit for the gender switch, but
Drinking my Baby Goodbye by Charlie Daniels would work.
Pretty Pathetic - The Smoking Popes
Great twist ending too!
“Don’t Ask Me Why” The Eurythmics
or post Eurythmics Annie Lennox, “Why” or “No More I Love Yous”
I thought you should know by Steve Earle
Not sure how many of these are going to be available in karaoke form…
“You’re Breaking My Heart,” Harry Nilsson
“You’re Gonna Miss Me,” The 13th Floor Elevators
“Feel A Whole Lot Better,” The Byrds
“Ain’t Nobody Home,” B.B. King
“I Hear You Knockin’,” Smiley Lewis/Dave Edmunds
“I’m Movin’ On,” Hank Snow
“When I’m Gone,” Brenda Holloway
“I Don’t Love You,” Teddy Pendergrass
“Most Likely You Go Your Way (And I’ll Go Mine),” Bob Dylan
'Positively 4th Street," Bob Dylan
“Every Time You Go Outside I Hope it Rains” by the Burch Sisters.
“I ain’t going to wish you all the best
I hope you’ll be lomesome, stay worried and depressed
I can sum it up so well with this refrain
Every time you go outside I hope it rains”
Also, “Thank God and Greyhound” by Roy Clark
“Thank God and Greyhound, you’re gone
That load on my mind got lighter when you got on
That shiny old bus is a beautiful sight
With the black smoke a-rollin’ up around the tail light
It may sound kinda cruel but I’ve been silent too long
Thank God and Greyhound, you’re gone.”
“They’re Coming To Take Me Away, Ha Haaaaaa!”
by Napoleon XIV
(That’s definitely about a breakup!)
(A man and his dog)