By my count, in the history of popular music, there have been 14 million love songs, give or take. These are songs about the glories of falling hard for someone and singing the praises of whoever he or she may be. It is the single most popular topic for any song, regardless of genre.
Coming in a close second is the heartbreak song. There have been 13.5 million of those, give or take. The majority of them are heartfelt tear-jerkers about how much I miss you or how I am moving on despite the pain. Many of them take a mature view of relationships and, at their core, indicate emotional growth – a kind of older but wiser ethos.
Those are not the kinds of songs we will be discussing today.
In honor of Valentine’s Day, 2025, when the world seems to be spinning madly out of control for many people, we’re talking about the other kind of breakup-up song. The kind that does not forgive and forget. The kind of song that clearly, obviously, even nakedly, holds a grudge. A big f*****g grudge. (Spoiler Alert: that censored term will be figuring into what follows in a significant way.)
Songs to rage to if you are having a vindictive Valentine's Day
I’ve noticed these types of songs have been around forever and fall into one of three sub-categories. So, assuming I am the aggrieved party and you are the SOB who broke my heart, I might go the passive-aggressive route. The “no hard feelings but my life sucks now” route. Or, I might simply express my hurt by projecting evil outcomes onto you. They may be real or imagined. As in the famous title of Spooky Tooth’s 1973 album You Broke My Heart So I Busted Your Jaw (which, sadly, did not have any songs worthy of that name).
The third option is the most straightforward. I just tell you what a colossal dumpster fire of a human being you are. No passive – all aggressive.
Now, though I do intend to choose a range of songs from different genres and different eras, I am ruling out a few. No hip hop. I could probably fill the entire list with “Eminem kills Kim” songs or classic sexually-inspired dis tracks. I’ll leave that to others. Besides, the only song I’m really sacrificing with this prohibition is Scroobius Pip’s “You Will See Me,” and I’m not sure I entirely understand that song.
And no Taylor. I mean, that kind sounds like a list all to itself, right?
All right, fine – if you need a Taylor song, go back to the start and choose “Picture to Burn.” That kind of gets at what I’m looking for today. I mean, who doesn’t hate their ex’s stupid old pickup truck?
With those disclaimers out of the way, here is your vindictive Valentine’s playlist for 2025, in chronological order.
“I Shot Mr. Lee” by the Bobbettes (1960)
For those of you who cling to the myth that violence didn’t exist in the 1950s, check out the way the Bobbettes closed the decade. One of the early girl groups had scored a big hit with the love song “Mr. Lee” in 1957. In that version, Mr. Lee was “the handsomest sweetie that you ever did see.” A few years later, the opinion had changed. The famous “One, two, three – Look at Mr. Lee – Three, four, five – Look at him jive…” had been reconsidered….
“One, two, three – I shot Mr. Lee – Three, four, five – I got tired of his jive…”
“Don’t Think Twice, It’s All Right” by Bob Dylan (1963)
It's the definitive passive-aggressive breakup song. Dylan could write sad heartbreak as well as anyone (“If You See Her Say Hello”) He could also be as vicious and angry as anyone (“Idiot Wind”). The fact that both those songs were on his monumental Blood on the Tracks album gives a hint of how complete a depiction of breakup it was. “Don’t Think Twice…” comes much earlier.
More than a decade earlier, from 1963’s The Freewheelin’ Bob Dylan, written when he was just 22. His simple finger-picked acoustic guitar and mournful harmonica are all that accompany this passive-aggressive gem…
“I ain’t sayin’ you treated me unkind – You could have done better but I don’t mind – You just kind of wasted my precious time – But don’t think twice, it’s all right.”
“You’re So Vain” by Carly Simon (1972)
Leslie Gore had gotten to number 5 back in 1963 with “Judy’s Turn to Cry.” It’s not a vindictive breakup song. It’s actually a vindictive “getting back together” song. Now the bitch who stole my man will suffer. (Insert sinister mustache twirl.) It’s as close to a big pop hit based on vengefulness as I know from the early days.
A decade after Leslie laughed while Judy cried, Carly took pure spite directed at an ex all the way to Number One. Just who the ex was has been debated ever since. Simon herself eventually said it was based on a composite of three men. That may be true, but we all know it was Warren Beatty. I don’t need to know the others.
“Well you’re where you should be all the time, and when you’re not you’re with - Some underworld spy or the wife of a close friend, wife of a close friend, and – You’re so vain – You probably think this song is about you…”
“Go Your Own Way” by Fleetwood Mac (1977)
One of the things that made Rumours the sensation that it was in 1977 was its emotional rawness. Both couples in the band were going through breakups, and they sang about it in perfectly composed and produced pop-rock songs. The lead single was Lindsay Buckingham’s reaction to his longtime girlfriend Stevie Nicks’ decision to end their relationship. Nicks got to respond with “Dreams,” the album's second single. But first, she had to sing background on a song she knew was all about her.
“Tell me why everything turned around – Packing up, shacking up’s all you want to do…”
“Little Miss Can’t Be Wrong” by the Spin Doctors (1991)
The jam band wrote three great pop-rock tunes on their debut album. Two of them – “Two Princes” and “Jimmy Olsen’s Blues” came from a mainstream tradition of the underdog boy trying to woo the girl against heavy odds. He’s poor, or he’s not Superman. You know the story. But the first single was a breakup song. A rather angry, spiteful breakup song, as you can probably guess from the title. If not, check out the opening couplet…
“It’s been a whole lot easier since the bitch left town – It’s been a whole lot happier without her face around…”
“You Oughta Know” by Alanis Morissette (1995)
The standard-bearer. I mean, it doesn't get angrier than this. The Bobbettes may have been inspired to shoot Mr. Lee, but they seemed downright happy about the whole affair. I guarantee you they were not one-tenth as pissed off as 21-year-old Alanis Morissette was on her first big hit.
After her tortured opening vocal in which she dives into new depths of passive aggressiveness, telling her ex that she’s happy for him, she pops the cork on the emotion and sweeps us all away…
“Did you forget about me, Mr. Duplicity – I hate to bug you in the middle of dinner – It was a slap in the face, how quickly I was replaced – And are you thinking of me when you f**k her?”
“The Last Song” by Sleater-Kinney (1995)
Was there something going on in 1995? Was it Bill Clinton? Or maybe it was the gloves coming off from the conformist 1980s and allowing artists – especially female artists - to express difficult emotions in raw terms. That’s what Carrie Brownstein and Corin Tucker did on their debut album. It came screaming out on the final track, with its double entendre title.
“This time I found it – I know how to scream – I don’t owe you anything! – I’m not part of you! – You can’t take away everything! – I’m not of you!”
“Gives You Hell” by The All-American Rejects (2008)
On their second album, the Rejects seemed content with keeping their romantic partner a dirty little secret. By the third, they seem to have broken up. But Tyson Ritter seems very happy with the whole thing. Ritter has said the song was inspired not by a romantic breakup but is directed at anybody who didn’t treat you right. But the lyrics are definitely directed to a past flame.
And although he seems to be falling into the old “living well is the best revenge” trope, he still admits he would like it very much if the second-person object of the song suffers mightily.
“I wake up every morning with a big smile on my face – And it never feels out of place – And you’re still probably working at a nine-to-five pace – I wonder how bad that tastes.”
“F**K You” by CeeLo Green (2010)
OK – this is not technically an angry song directed at a past lover. As such, maybe it shouldn’t be on this list. It’s just such a fun, direct song that is related to the subject that I figured I’d throw it in at the midpoint. CeeLo is a complicated figure in the world of modern pop. Musically, he has been capable of sublime moments, Personally, he has seemed to go out of his way to sabotage his career.
In 2010, he was riding high with this upbeat tune co-written with Bruno Mars about that awkward moment when your best friend starts dating your ex. And all you can say is “forget you” – which was the radio-friendly edit used in place of the censored title above. And to be clear, though the song is mostly directed at the friend, the woman is not immune …
“I guess the change in my pocket wasn’t enough – I’m like, f**k you and-a f**k her too”
“P.S. I Hate You” by Reel Big Fish (2012)
This is not the Beatles. Fifty years after the Fab Four released “P.S. I Love You” as the flip-side of “Love Me Do,” Reel Big Fish applied their horns and their up-tempo ska beat to a different message. Aaron Barrett may not have been in the best of moods when writing the songs for Candy Coated Fury.
With titles like “Everyone Else is an A*****e” and “Your Girlfriend Sucks,” you kind of get the idea that no matter how insanely catchy the tunes are, there’s a wee bit of darkness lurking underneath. He doesn’t really hide any of it on the second-to-last track…
“Well, when we first met, if I’d only known – I would have run for my life, I would have left you alone – You’re evil and vicious and cruel and cold – That’s you, that’s you”
“(This Song is Definitely Not About a Boy)" by Makeshift Shelters (2015)
DC’s Makeshift Shelters released their first album in 2015. By the time I heard it a year later, the band no longer existed. In glorious passive aggressiveness splendor, their announcement went like this – “we’re breaking up because whatever.” What a shame. Ella Boissonnault’s brutal takedown of a former boyfriend rivals prime Alanis Morissette. She formed Lady Pills after the breakup and has a new album coming out later this year.
“I was pretty young and I was pretty dumb – Because somehow you convinced you were great – But you’ll never get those ugly sweaters back – and by the way that was a really sh***y mixtape”
“Vomit” by Microwave (2016)
Now this is sophisticated revenge. It begins as a pretty typical emo whine from the Atlanta band, complaining about a relationship gone bad. After the relative calm of the first verse, the gloves come off in a melodic metal scream.
“So I pull you drawers and fill up your sink – Make everything exactly how you hate it all to be – ‘Cause I’m not trying to hold your hair – No, love won’t pass through me – ‘Cause I’m far too cynical for faith and make believe.”
“F**k You Bitch” by Walker Wheeler, Jr. (2016)
I probably don’t have to explain much here, right? Most of the titles on Wheeler’s debut album Redneck S**t can’t be said out loud in polite company. It is camp and country rolled into one, kind of what Bloodhound Gang does for rap rock. This song is just so on the nose.
“F**k you bitch, you broke my heart – F**k your friends, tearing us apart – F**k your dog, hope he never comes home – F**k you bitch, hope you wind up alone.”
“good 4 u” by Olivia Rodrigo (2021)
I promised no Taylor. I said nothing about Olivia. Musically, this smash hit from her debut album may have been modeled on Paramore, but its message is a direct descendant of Morissette and Makeshift Shelters. I’m sensing she doesn’t really mean it when she screams out the title lyrics.
“Well good for you, you look happy and healthy – Not me if you ever cared to ask – Good for you, you’re doing great out there without me, baby – Like a damn sociopath.”
“Kill Bill” by SZA (2022)
We began with the Bobbettes joyfully shooting Mr. Lee. Now that we are almost at the end, we come full circle. SZA’s dream pop revenge song blurs the lines between fantasy and reality. It was nominated for multiple Grammys and probably should have won Song of the Year. A theme song for sociopathic lovers the world over.
“I might kill my ex – Not the best idea – His new girlfriend’s next – How’d I get here? – I might kill me ex – I still love him though – Rather be in jail than alone.”
“Fell in Love With a Piece of S**t” by Mellohoney (2024)
To be honest, I was finished with the list of 15 songs. Then I heard this one, from a Canadian band with whom I was not familiar. On this decidedly anti-love song, they kick it into gear like a stripped-down Flogging Molly from the great white North, beginning on an almost romantic note before getting to what they really wanted to say.
“I took you to mother, to father, to friends – They did not approve of your irreverence – They told me you’re lying, callow, and selfish – That I gave my heart to a piece of s**t.”
And what more is there to say? Happy Valentines Day.