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. If you’re alone on this holiday, fire up our playlist and cry as you read along. And if you’re happily attached, just appreciate the songs—and your relationship. After all, you can’t fully appreciate a breakup song until you truly know what it’s like to lose in love.

It all started so simply. Innocently. Tenderly. “He’s the reason for the teardrops on my guitar.”

The second single from Taylor Swift’s self-titled debut album wastes no time with metaphor. She names names. Sets scenes. Explains precisely how painful it is to watch her high school crush crushing on someone else. At just 16 years old, Swift wrote a heartbreak anthem that was both extremely personal and also applicable to millions. And that was just the beginning.



Despite what this very website’s ranking of breakup songs may suggest, Taylor Swift has had a musical stranglehold on heartbreak for the last 13 years. Taylor Swift alone features “Tim McGraw,” “Teardrops on My Guitar,” “Picture to Burn,” “Cold as You,” and “Should’ve Said No.” Two years later came Fearless, with gut-wrenching songs like “Fifteen” (“‘Cause when you’re 15 and somebody tells you they love you / You’re gonna believe them”), “White Horse,” and the power ballad “The Way I Loved You.”

Those songs are each about specific relationships and situations, but they all share a special kind of clarity. There is no artifice in Taylor’s prose, no lines designed to be Instagram captions (or well, I guess back then AIM away messages). She says exactly what she feels, whether she misses the messy toxicity of a boy who’s wrong for her in all the right ways, or that she’s finally realized the fairy-tale ending she envisioned wasn’t going to come true. She communes so easily with herself that each song feels like its own therapy session.

Some of that honesty certainly comes from Swift’s roots in country music, which prizes storytelling and drilling down to the heart of an idea more than anything else. But most of it just stems from her—this special, clear-eyed girl who somehow connects with people across gender and age lines despite being pitched as the Teenage Girl Whisperer.

At some point, though, as Swift’s fame grew and her suitors changed from the likes of Drew and Stephen From High School to guys like John Mayer and Jake Gyllenhaal, the ideas in her songs grew more complicated. From “Dear John,” the fifth song on her third album, Speak Now: “You paint me a blue sky / then go back and turn it to rain / And I lived in your chess game / but you changed the rules everyday.” And from “Back to December”: “These days I haven’t been sleeping / staying up playing back myself leaving.”

The forces of celebrity and going from high school romances to ones with famous older men really start to take their toll in Speak Now. Swift is still acutely self-reflective, but her feelings become more muddied, more confused. How’d things get to this point? Which way is up? Where do I get off this ride? And as the nature of her relationships changed, so did the reception to her songs.

Rather than focusing on the universal themes that came from “Dear John” or “The Story of Us,” people were parsing Swift’s lyrics for clues about her famous exes and what led to their splits. Swift’s penchant for honesty and openness wasn’t viewed as powerful songwriting anymore, but instead morphed into an ugly idea that if you dated Taylor Swift, you were just fodder for her next tell-all song. The beauty of her profound thoughts on heartbreak were missed through the trees of juicy details about her latest relationship. Lucky for us, though, that didn’t change Swift’s writing.

In 2012, Swift released the mother of all love/heartbreak/breakup albums: Red. Yes, the album contains a few songs that were seemingly designed to be radio hits—“Red” itself, “We Are Never Ever Getting Back Together,” and the oft-meme’d “I Knew You Were Trouble”—but the deep cuts are truly some of Swift’s finest work. There’s “Sad Beautiful Tragic”: “In dreams, I meet you in warm conversation / We both wake in lonely beds, in different cities.” Then “Come Back...Be Here”: “And now that I can put this down / If I had known what I know now / I never would have played so nonchalant.” But her crowning achievement comes with the fifth track on the album, “All Too Well.”



The entire song is worth quoting, from the opening salvo where she describes leaving a scarf at her boyfriend’s sister’s house—one that he still keeps in a drawer even after their split—to her closing demands that he remember it all, just like she will. But the bridge, which Swift scream-sings in an almost desperate fashion, is the real triumph:

And you call me up again just to break me like a promise

So casually cruel in the name of being honest

I’m a crumpled up piece of paper lying here

’Cause I remember it all, all, all

Too well

Whew!

One of Swift’s cowriters, Liz Rose, has said this was the first song Swift wrote for the Red album, and that it was arguably one of her hardest ever to get down on paper. So many details spewed out from her memories—plaid shirts, dancing in the refrigerator light, autumn leaves, almost running a red light because she and her beau were too busy looking at one another to notice. Swift said that if she included everything she wanted to, the song would have been 10 minutes long. And for how good it is, it could have been. But that detail is what makes Swift’s writing so special. Even after half a decade in the spotlight, she wasn’t afraid to share the intimate, vulnerable details that made her relationship what it was. While others get by on clichés and turns of phrase to explain heartbreak, Swift thrusts it forward in all its gory detail and lets you take from her experience what you want.

After Red, Swift shifted more fully into pop music. She still presented some complicated themes on 1989, like the back-and-forth romance you just can’t quit (“Style”) and those times a relationship is “built to fall apart / Then fall back together” (“Out of the Woods”), but the album at large focused much more on playing with the narratives that had formed around her. “Blank Space” mocks the idea that she dates only to get more material for her songs. “Bad Blood” talks about friendships she’s lost to silly squabbles and fame wars.

That trend continued into Reputation, which was much more of an album-long dig at Kim Kardashian and Kanye West—and somewhat of a celebration of her happy relationship with Joe Alwyn—than anything resembling a deep examination of personal anxieties. But on Lover, which was released last August, we see a brief return to form in “The Archer.”

I’ve been the Archer, I’ve been the prey

Who could ever leave me darling

But who could stay?

“The Archer” is more of a production than her past heartbreak songs, but even through the thudding Jack Antonoff–crafted beat, there’s a piece of that tenderness and reflection that we saw during her country days. She asks, “Can you see right through me?” Confesses, “I cut off my nose just to spite my face.” Begs, “Help me hold onto you.”

It’s that final sentiment of the chorus, though, that seems to sum up all of Swift’s decade-plus thoughts on heartbreak. Who could ever leave me? That’s expressed in all her defiant anthems: “Picture to Burn,” “Should’ve Said No,” We Are Never Ever Getting Back Together,” “All You Had to Do Was Stay.” But the answer to that follow-up question, Who could stay?, is seemingly what Swift has been searching for all along.