Best Falling-out-of-love songs

A handful for submission -

The Cars - Drive

REO Speedwagon - Time For Me To Fly

John Mayer - Slow Dancing in a Burning Room

Mayer Hawthorne - Just Ain’t Gonna Work Out

Ryan Adams - Harder Now That It’s Over

Ryan Adams - How Do You Keep Love Alive

The absolute best song for me of this genre is

The Heart Of The Matter by Don Henley.

Also good, if not quite right is

Nothing Better by The Postal Service

Those pronouns, and the examples offered earlier in the thread, suggest that you’re only interested in songs where the singer/narrator expressing the hostile and contemptuous sentiment for the former partner is male.

However, if that’s not the case, I think Nancy Sinatra’s These Boots Are Made for Walkin’ would fit your criteria too.

Fuckin’ A. That song is the best. Know it practically by heart.

Cry Cry Cry, by Johnny Cash.

Argh - I missed the designation of contemptuous *only

*Does not take direction well.

The original’Fuck You’ - Harry Nilsson

“I’m Not Angry” by Elvis Costello

Positively Fourth Street - Bob Dylan

“Sail On” - The Commodores

Oh there are a million great ones.

The dB’s Black and White

Peter Case kicking ass in The Nerves’ When You Find Out

The master, Gene Clark, with the Gosdin Brothers in I Think I’m Gonna Feel Better

Amazing live video of the criminally underrated Artful Dodger KICKING ASS with It’s a Lie

Well this counts, I think, about not taking shit from a girl playing hard to get? Anyway, a pop masterpiece from The Rubinoos

The best thing to happen to power pop/punk since the 80s, of course, has to literally die. Go figure. But you can’t kill amazing songs. The Exploding Hearts’ Sleeping Aides and Razor Blades

Perhaps a bit upset about a break up, but still cool as hell, Merle Haggard is going to break every woman’s heart in the world. And he probably could.

I will represent the homeland of Canada with some of the best: Pointed Sticks’ Lies. And also how about I’m Numb, because Pointed Sticks rule.
There is so much–too much. It really could go on forever. Cool songs for miles.

I don’t know if this counts: Somebody’s Gonna Love You by Matt Wertz. It isn’t an angry song. It’s more of a you and I both are wasting time and, as of now, we’re just fighting the inevitable trying to stay together.

John Mayer - Clarity

And I will wait to find
If this will last forever
And I will wait to find
That it won’t and it won’t
Because it won’t
And I will waste no time
Worried 'bout no rainy weather
And I will waste no time
Remaining in our lives together

Jackson Browne-I’m Alive

Yeah, now I’m rolling down
This canyon drive
With your laughter in my head
Gonna have to block it out
Somehow, to survive
Cause those dreams are dead
And I’m alive

What about Every Breath You Take by the Police? It’s from the point of view of someone stalking his ex-lover who feels if he can’t have her, then no one else can. I would say he no longer cares about his ex, he only wants to possess and control her.

“29 Nights” Danni Leigh
It’s been thirty long days, twenty-nine nights
And I’m still over you

“Irreplaceable” - Beyonce
I can have another you in a minute
As a matter of fact, he’ll be here in a minute

Don’t Think Twice, it’s All Right by Bob Dylan

I kinda like Travis Tritt’s Here’s a Quarter, Call Someone Who Cares. Country Western is really the best style of music for this type of song.

This early Linda Ronstadt number was always a favorite of mine:

Dar Williams - The Pointless, Yet Poignant, Crisis of a Co-ed