What makes a song a “breakup song”? In honor of Valentine’s Day, The Ringer is digging deep into the genre with our ranking of the 50 greatest ones in music history and pieces exploring the current state of the heartache anthem. And because the agony of breaking up is such a singular experience, we’re including a handful of our personal favorites that didn’t make our final list.
“Anytime,” Brian McKnight
When I got to the end of the list of breakup songs that us Ringer staff members voted on, I immediately hit command+F and typed “McKnight.” Anguish set in. There were zero instances of “McKnight” in the entire document. How could this be? The lights in my apartment dimmed to darkness and all my candles spontaneously sparked to life. Somber piano flourishes arose out of thin air and enveloped me. My head fell into my hands. Brian McKnight’s “Anytime,” one of the greatest breakup songs of all time, was somehow not even on our initial list of breakup songs.
Cowritten by McKnight and his frequent songwriting partner Brandon Barnes, “Anytime” was inescapable in 1998. Despite not even being officially released as a single, “Anytime” topped the Billboard Hot 100 list and spent 76 weeks on the chart. It was played nonstop on radio stations and MTV. Everywhere you turned, there was Brian McKnight’s supernaturally emotive voice laid on top of that devastating piano melody. When I revealed to several coworkers that “Anytime” had been omitted from our list of breakup songs, there were audible gasps.
“Anytime” is a soundtrack for late-night longing and unhealthy thought experiments. It’s a whiskey-soaked diary entry detailing how difficult it is to reconcile a lush past with an empty present. How can it be that what was once such a strong, tangible connection is now completely gone? How can I know nothing about someone I once knew everything about? Do I ever cross your mind, anytime? These are torturous, unanswerable questions. But the one certainty that’s clear for McKnight is echoed in a refrain that draws immense power from its simplicity: “I miss you.” —Matt James
”No Children,” The Mountain Goats
A breakup song typically mourns the end of a relationship. Few actually celebrate that trauma. Mountain Goats founder John Darnielle’s 2002 opus is one of those. The exhausted narrator spends nearly three minutes bashing his soon-to-be ex and himself. Take “Hit ‘Em Up,” infuse it with tinkly piano, twist half the lyrics inward, and you get “No Children.”
“I hope you die,” the chorus famously crows. “I hope we both die.”
The gleefully bleak ode to the destruction of a toxic marriage wouldn’t be so beloved—NPR recently dedicated a segment of its American Anthems series to it and it’s sung at weddings—if it weren’t also uplifting. After all, splitting apart from a longtime partner can be such a goddamn miserable slog. Sometimes all you can do is scream and laugh. That’s what this song provides: a release.
“Silver Springs,” Fleetwood Mac
When Stevie Nicks wrote “Silver Springs” in 1976, during a messy breakup with her bandmate Lindsey Buckingham, she was thinking, “I’m so angry with you. You will listen to me on the radio for the rest of your life, and it will bug you. I hope it bugs you.” Wanting to rub your greatness in an ex’s face is a pretty common sentiment, but Nicks took it to a whole new level with “Silver Springs.”
The original recording of the song, released as a B-side on the first single for Rumours after having been cut from the album, is a breakup banger, full of love and rage in equal measure. As Nicks intended, the song lives on, blasting from jilted lovers’ earbuds today. But the real proof that she won the breakup is a 1997 live performance, taped during a Fleetwood Mac reunion show. Twenty years after the band recorded Rumours—and, more importantly, 20 years after the split that launched “Silver Springs”—Nicks and Buckingham are back on the same stage, singing the song that she wrote expressly to ensure he’d never forget the relationship he’d lost. She’s armed with great hair and a death stare, which she turns on him during the song’s climax. You can literally see the sweat bead on Buckingham’s temples as Nicks sings, “You’ll never get away from the sound of the woman that loves you.” She’s right; he never did. —Charlotte Goddu
“Divorce Song,” Liz Phair
“Divorce Song” starts mid-breakup, deep into the road trip from hell: “And when I asked for a separate room / It was late at night, and we’d been driving since noon.” It’s not the drive that’s killing them, however—it’s the relationship. Over the course of three minutes and 20 seconds, Phair recounts all the microaggressions that signal this thing is coming to an end. Yes, she stole his lighter, and yes, she lost the map. But how could he speak to her like that? It all builds to a crushing crescendo before the last chorus: “And the license said you had to stick around until I was dead / But if you’re tired of looking at my face, I guess I already am.”
“Divorce Song”—the centerpiece of Exile in Guyville, one of the greatest breakup albums of the ’90s—is a vignette of moments specific to her breakup, but if you’ve ever flailed through a dying romance, they feel so universal. —Justin Sayles
“Answering Machine,” the Replacements
“Answering Machine” might be the perfect Replacements song. The beauty of the Mats always lied in their incongruities. This was a band that could trash their Saturday Night Live dressing room so thoroughly that they were never invited back, and that could also cut all the way through you. “Answering Machine” starts with the same sort of big Bob Stinson riff that opens a lot of Replacements songs, and that aggression only serves to amplify the tenderness that follows. You can feel the loneliness as Paul Westerberg describes a life on the road and the longing for that one person that slows the world down. When he asks how you say “good night” to an answering machine, there’s a bite to it. He’s sad, frustrated, and, ultimately, alone. It’s a song about wanting a life that no longer exists, with a person that he can longer have. Grounding that emotion in sounds (that awful, familiar beep) and an image (that rolling cassette deck sitting on the counter) anyone who grew up in the ’80s or ’90s will understand just amplifies the pain. There are only so many songs that no other band could write. This is one of them. —Robert Mays
“Smile,” Lily Allen
Living well is the best revenge, but a little schadenfreude along the way doesn’t hurt.
“Smile” is firmly in the Gloria Gaynor “I Will Survive” tier of breakup songs (see also: “Since U Been Gone,” “Thank U, Next,” “Irreplaceable”). It’s a cathartic anthem for when you can look back at the dark days and move forward as a stronger person. The Rocksteady beat and piano riff (sampled from Jamaica’s Soul Brothers) and Allen’s dry delivery are a match made in heaven, unlike the relationship in question.
Every time you think she’s being a little too callous she reminds you that it’s all for a reason. Her matter-of-fact delivery of “See you messed up my mental health / I was quite unwell” course corrects any misgivings about a jilted ex. When she sings that she made it through with the help of her friends? You love to see it. —Kjerstin Johnson
“Here, My Dear,” Marvin Gaye
There are breakup albums, and then there’s Here, My Dear. Panned upon its release in 1978, the album has come to be regarded as one of the great musical heartache documents of all time. That’s largely because of its backstory: As part of his divorce settlement, Gaye agreed to give half of the royalties of his next album to his ex-wife. That album ended up being Here, My Dear, a double album composed of songs such as “When Did You Stop Loving Me, When Did I Stop Loving You,” “Anger,” and “You Can Leave, but It’s Going to Cost You.” You don’t have to read much into the songs to see where Gaye’s head was at, but he lays it all bare in the spoken interlude that opens the album: “I guess I’d have to say this album is dedicated to you / Although perhaps you may not be happy / This is what you want, so I’ve conceded / I hope it makes you happy / There’s a lot of truth in it, babe.” —Sayles
“Pictures of You,” the Cure
Examining a relationship in the rearview is an inherently subjective experience—we’re prone to romanticizing the good times, wallowing in the hard times, wondering what we could have done differently, unduly assigning or accepting blame. Robert Smith wrote the best song about that feeling (and my favorite song, period) in “Pictures of You.” It’s the lush centerpiece on the band’s opus Disintegration, played on John Hughes synth pads, wind chimes (!), a series of earworm riffs played on a six-string bass, all over a trademark Boris Williams drumbeat. “I’ve been looking so long at these pictures of you / That I almost believe that they’re real,” Smith croons, longing for a time and an ex that he spends the verses remembering (or misremembering) through rose-colored lenses.
In 1989, Smith said of the song “The idea you hold of someone isn’t really what that person is like. Sometimes you completely lose touch with what a person has turned into. You just want to hold on to what they were.” And that’s what it is—a faded snapshot of someone in the exact moment that you choose to remember them by. —Cory McConnell
“Lost Cause,” Beck
I have to assume that the reason there wasn’t a song on our list from Beck’s masterful 2002 album Sea Change is because it’s such a consistently strong album that it’s hard to point to any one song as the definitive standout. It’s 12 tracks of tear-jerkers from a broken man who’s equal parts numb and pained; 98 percent devoid of hope. I’ve chosen “Lost Cause,” but the details of a particular heartbreak could just as easily lead you to any of the 11 other songs.
“Lost Cause” is an emotionally drained and exhausted Beck learning to resist his impulse to help his now former lover. After so much time and effort invested in someone, it’s an alien feeling to completely divorce their problems from yours. Feeling taken advantage of, Beck wonders how his now former lover will navigate the world without him.
Cuttingly, he sings “There’s a place where you are going / You ain’t never been before / No one left to watch your back now / No one standing at your door / That’s what you thought love was for.” You can put everything you’ve got into a relationship, but if your partner isn’t looking to give as much as they’re looking to take, it’s a lost cause. —James
“Never Meant,” American Football
Let’s just pretend
Anything between you and me
Was never meant
Considered by many to be the greatest emo song of all time, “Never Meant” is about trying to move on and forget. But that’s easier said than done—Mike Kinsella’s pleas are ostensibly directed at his soon-to-be ex-lover, but it sounds like he’s trying to convince himself. No breakup song list is complete without this on it. —Sayles
“Poke,” Frightened Rabbit
Frightened Rabbit’s 2007 album The Midnight Organ Fight has at least four generationally great breakup songs. There’s the fan-favorite “Keep Yourself Warm” (a part of the chorus that’s preceded by “it takes more than fucking someone to”), and there’s “My Backwards Walk,” which feels like the song Chris Martin wanted to write with “The Scientist.” There’s the mournful “Floating in the Forth,” which eerily foreshadowed how singer Scott Hutchison would eventually die by suicide. But for me the best one is “Poke,” a sparse, mostly acoustic tune in which Hutchison doesn’t sort through the end of a relationship as much as he screams and sobs into the waste bin that its wreckage occupies.
It’s everything that makes a great Frightened Rabbit song—it’s painfully honest, occasionally funny, and unbelievably sad. Fitting of the song’s title, listening to it feels like poking at an old wound, digging deeper into it to try to make sense of it. Early in the song he sings, “We adopt a brand new language / Communicate through pursed lips,” underscoring the way in which lovers’ secret code turns into antagonistic lawyer jargon as communal stuff gets split up, bars and haunts are territorially marked, and friend groups choose sides. For the late Hutchison, breakup songs were his language, spoken and understood by anyone who counted themselves as a fan, and by anyone familiar with heartache. “Poke,” and the rest, are all the more gut wrenching in his absence. —McConnell
“None of Your Concern,” Jhené Aiko Featuring Big Sean
We all know that Jhené Aiko and Big Sean’s on-again, off-again relationship is nothing short of toxic. I mean, she got HIS FACE tattooed on her arm after a year of dating—who does that? The lyrics to this post-breakup ballad are clearly about her most recent ex, and on first listen, I was fist-pumping in support. Lines like, “I know that I’m deserving of more” and “not scared to be alone anymore” nearly crowned it as a self-love anthem. Then, after a brief pause, Big Sean comes on the record! And starts rapping about her! “Yeah, you know I had these issues when you met me,” he raps. What’s better than two ridiculously talented people—who are pretty bad at relationships, I might add—essentially arguing in a well-crafted song? If anything, I was upset that the song ended on Big Sean’s verse and Jhené didn’t get a rebuttal. —Jordan Ligons
“Before He Cheats,” Carrie Underwood
Look, I don’t care what quantity of CBD you ingest each day or how many years of therapy you’ve been through, even the most enlightened of us have fantasized about exacting revenge upon an ex. “Before He Cheats” describes the destruction of one man’s customized four-wheel drive with such feverish detail that it’s essentially ASMR for the romantically scorned, a cathartic, slightly unhinged victory dance atop the ruins of a relationship too far gone to salvage. While I don’t necessarily endorse property damage, I do think the musical expression of rage—particularly female rage—is underrated. And judging from the number of women I’ve seen angrily sing this song at karaoke, we’d all be a little better off if we expressed ourselves with the same reckless abandon as Carrie Underwood. —Alyssa Berenzak
“Angie,” the Rolling Stones
As with so many of the great breakup songs, from “You’re So Vain” to “You Oughta Know,” it’s tempting to get to the bottom of exactly whom (or what) this song is about. Writer Keith Richards’s muse Anita Pallenberg? Their daughter Dandelion Angela? David Bowie’s wife Angie? Heroin? Mick Jagger’s love Marianne Faithfull? The list goes on and on, but it also doesn’t matter: “Angie” is the honest, doomed accounting of the loving in one’s soul and the money in one’s coat, and what’s more universal than that? Some breakups involve screaming and throwing plates; others are quiet, even tender. “Angie” describes the latter, lamenting the ravages of time and circumstance, quietly talking itself into saying goodbye for everyone’s good. —Katie Baker