Taylor Swift's 15 best breakup songs, ranked

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Taylor Swift's 15 best breakup songs, ranked
  • Taylor Swift has perfected the art of the breakup anthem.
  • Her lyrics explore a range of post-heartbreak feelings, from regret and anger to despair and yearning.
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15. "The Story of Us"

15. "The Story of Us"
"The Story of Us" was released as a single in 2011.Taylor Swift/YouTube

While promoting "Speak Now," her entirely self-written third album, Swift told New York Magazine, "It's not like I am bulletproof in any sense of the word."

Luckily, Swift's thin skin and tender heart are two of her most valuable weapons as a songwriter. In the album's fourth single, "The Story of Us," we see how brief interruptions in her life are turned into massive ruptures, commensurate to the pain they cause.

A run-in with an ex at an awards show is spun into a tragic epic of Odyssean proportions. A "simple complication" ends in agony. A moment of silence becomes a scream.

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14. "Forever & Always"

14. "Forever & Always"
"Forever & Always" is the 11th track on "Fearless (Taylor's Version)."Theo Wargo/WireImage

"Forever & Always" walks a delicate line between fretting and sneering. After Swift opens the song with an image of budding romance and reassurance, she immediately quips, "Were you just kidding?" Later, she accuses her ex of running away from earnest affection "like a scared little boy."

But for all her projected strength, Swift is still tortured by these questions. You can practically hear her pacing around her bedroom, still caught in the fever of first love, trying to pinpoint the moment when it all went wrong.

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13. "Last Kiss"

13. "Last Kiss"
"Last Kiss" is the 13th track on "Speak Now."Larry Busacca/Getty Images

The release of "Speak Now" marked a distinct period of growth in Swift's life. As Jon Caramanica noted for the New York Times, her first two albums were partially shrouded by daydreams and high-school dalliances.

After "Fearless," Swift was forced to live in the open air — and in the spotlight.

"In these new songs relationships are no longer fantasies, or neutered; they're lived-in places, where bodies share space," Caramanica wrote.

The gut-wrenching, six-minute ballad "Last Kiss" bears the unmistakable bruises of lived-in places and warm bodies. The title itself evokes an intimate touch, a lingering tingle.

The sudden absence of those sensations makes them feel even more tactile and real: "The beat of your heart / It jumps through your shirt," "But now I'll go / Sit on the floor wearing your clothes."

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12. "Loml"

12. "Loml"
"Loml" is the 12th track on "The Tortured Poets Department."Beth Garrabrant

It's tough to determine the best breakup track from "The Tortured Poets Department." Either "So Long, London" (a slow-burn collapse) or "The Smallest Man Who Ever Lived" (a scathing takedown) would be worthy picks for an all-time ranking.

But "Loml" stands out as the album's most distraught memory. No one is quite sure who it's about, but that seems like the point; Swift sounds genuinely bewildered as to how this could happen. "You told me I'm the love of your life about a million times," somehow becomes "You're the loss of my life." Was it legendary? Was it momentary? How could it be both? It's almost like her fate has been warped, the timeline was corrupted, and now Swift finds herself in a reality she doesn't recognize.

"Loml" is full of phantoms and empty grave sites that anyone who's been in love would recognize. How could a relationship ever die when it once felt so alive? These are the questions that transform a Swiftian breakup song from emotional to harrowing.

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11. "Holy Ground"

11. "Holy Ground"
"Holy Ground" is the 11th track on "Red."John Leyba/The Denver Post via Getty Images

Swift's fourth album is packed with tear-jerkers and bangers ("Red," "We Are Never Ever Getting Back Together," "The Moment I Knew") that capture the confusion and agony immediately following a breakup. "Red (Taylor's Version)," even more so ("Better Man," "I Bet You Think About Me," "The Very First Night").

But the high-octane "Holy Ground" jumps out of the tracklist like an explosive.

The song kicks off with Swift explaining, "I was reminiscing just the other day." She tells this particular story with the benefit of hindsight; it's an anecdotal detour from the album's larger arc of love and loss. The heartbreak at its center is a few years removed, which allows Swift to play around with pace and perspective.

"Holy Ground" also brings a rare glint of humor to this ruinous list. The final couplet in the first verse, "I left a note on the door with a joke we'd made / And that was the first day," is the kind of self-aware punchline that 22-year-old Swift was destined to write. If you're itching to criticize her for falling too fast and too hard, she's already beaten you to it.

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10. "Picture to Burn"

10. "Picture to Burn"
"Picture to Burn" was released as a single in 2008.Taylor Swift/YouTube

It's well documented that Swift raised a new generation of songwriters, but "Picture to Burn" should have its own monument in her new republic. Grammy nominees like Olivia Rodrigo and Gayle have both cited the song as a childhood seed of inspiration and rebellion.

The fourth single from Swift's debut album is a thrilling, raucous ode to getting pissed off and lobbing threats at your shitty ex, even if they're really just delusions of grandeur. "Picture to Burn" isn't really a song about revenge, after all. It's about catharsis.

It's also one of Swift's best songs to sing in the car (preferably a pickup truck) with all the windows rolled down.

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9. "Hits Different"

9. "Hits Different"
"Hits Different" is the 21st track on "Midnights (The Til Dawn Edition)."Ethan Miller/TAS23/Getty Images for TAS Rights Management

"Hits Different," in all its '00s rom-com glory, should've been released as a single from "Midnights."

The song is so good that it transcends a title that's a little too on the nose. In fact, being a little too on the nose is the whole point of the song: "I pictured you with other girls, in love / Then threw up on the street," Swift sings in the first verse. She's pulling out all the stops and she's not embarrassed one bit.

The bridge, in particular, is brilliantly delirious, one of Swift's best yet. "You were the one that I loved / Don't need another metaphor, it's simple enough," she declares and then, in the very next breath, uses a simile and a film metaphor: "A wrinkle in time like the crease by your eyes / This is why they shouldn't kill off the main guy."

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8. "The Black Dog"

8. "The Black Dog"
"The Black Dog" is the 17th track on "The Tortured Poets Department: The Anthology."Beth Garrabrant

"The Black Dog" is the first track to introduce "The Anthology," the deluxe version of "The Tortured Poets Department."

It's also one of five songs on the double album that Swift wrote by herself, alongside other heartbreakers like "Peter" and "The Manuscript" — and it's easy to tell.

The storytelling in "The Black Dog" is so exquisitely Swiftian — modern yet classic, aching yet righteous, existential yet specific — it's no wonder fans have been flocking to the London pub that shares its name like some kind of pilgrimage. Swift has a knack for turning the sites of her heartbreak into sacred ground.

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7. "Champagne Problems"

7. "Champagne Problems"
"Champagne Problems" is the second track on "Evermore."Omar Vega/TAS23/Getty Images for TAS Rights Management

"Champagne Problems" is perhaps the least autobiographical song on this list, but it will resonate with any woman who fears this whisper behind closed doors: "What a shame she's fucked in the head."

Swift's narrator is headstrong yet remorseful, independent yet nostalgic. She didn't want to get married, but that doesn't mean she won't miss that familiar Chevy door swinging open, or a borrowed flannel draped around her shoulders in the crisp November air.

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6. "Death by a Thousand Cuts"

6. "Death by a Thousand Cuts"
"Death by a Thousand Cuts" is the 10th track on "Lover."Kevin Mazur/Getty Images for TAS Rights Management

Swift said she was inspired to write "Death by a Thousand Cuts" after watching Netflix's "Someone Great." (Fittingly, the film's writer and director Jennifer Kaytin Robinson was actually inspired by Swift's album "1989," especially its closing track "Clean," which will appear farther down this list.)

The film's protagonist, Jenny (Gina Rodriguez), is forced to reckon with the demise of her 9-year relationship after landing her dream job, which will take her thousands of miles away.

"It's a movie about how she has to end this relationship that she didn't want to end because she's still in love with the person, but they just grew apart, and he's not a jerk," Swift said on Elvis Duran's morning radio show. "It's just sad because it's just realistic. Time passed, and now we're different people, and that is the most devastating thing."

In "Death by a Thousand Cuts," Swift imagines a bygone relationship as a house she can't get into anymore. Now, she can only peer through the windows and catch glimpses of the flickering chandeliers. She goes through life begging for a clear sign — green means go, red means stop — only to be met with yellow lights.

And as if those verses aren't vivid enough, just wait for the bridge — a breathless inventory of moments, feelings, and body parts. They should belong to her now, but instead, they're constant reminders of the life she once shared.

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5. "Right Where You Left Me"

5. "Right Where You Left Me"
"Right Where You Left Me" is the 16th track on "Evermore (Deluxe Version)."Omar Vega/TAS23/Getty Images for TAS Rights Management

"Right Where You Left Me" is something like a spiritual sister of "All Too Well."

Swift doesn't forget stuff. It's her whole thing. In her own words, "I bury hatchets but I keep maps of where I put 'em."

But sometimes that superpower is her own worst enemy. When you remember everything that's ever happened to you — every touch, every kiss, every candlelit conversation — moments of solitude feel extra lonely. When you remember the contours of a lover's face like you're looking in a mirror, simply "moving on" just isn't an option.

"Right Where You Left Me" is the most acute illustration of yearning in Swift's catalog. She allows the dust to settle over her body, welcomes the muscle cramps from sitting eternally cross-legged.

Once the outro hits and she's openly beseeching her ex to return, it doesn't feel pathetic because she's brought you into the restaurant with her. Sitting in that seat, it feels like the only reasonable request.

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4. "Clean"

4. "Clean"
"Clean" is the 13th track on "1989."Liu Xingzhe/Visual China Group via Getty Images

As I previously wrote, "Clean" is the perfect closing track for "1989," an album that follows Swift as she struggles to recover from an on-and-off romance.

Swift and her cowriter Imogen Heap employ a swirl of twinkling synths, soothing melodies, and a cascade of metaphors to capture the suffocation of heartbreak — and the relief of taking your first deep breath on the other side, knowing what you went through to get yourself there.

The title is a particularly brilliant double entendre, with Swift comparing her healing process to both rain and sobriety.

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3. "The 1"

3. "The 1"
"The 1" is the opening track on "Folklore."Ethan Miller/TAS23/Getty Images for TAS Rights Management

"The 1" sets the scene for Swift's best and most haunting album.

Although several songs from "Folklore" could be on this list, "The 1" is a unique and precious gem in Swift's heartbreak arsenal.

It's a song that's less about breaking up with a person and more about breaking up as a concept. It's about missing a feeling of security and certainty that you never actually had — the greatest film of all time that was never made. It's about writing letters you'll never send, digging up graves, waiting at the bus stop, and waking up alone. It's wistful, melancholic, and cautiously hopeful all at once.

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2. "Dear John"

2. "Dear John"
"Dear John" is the fifth track on "Speak Now."Larry Busacca/Getty Images

When "Speak Now" was released, Swift wasn't shy about framing the album as a diary set to music. As she told Chris Willman for Yahoo! Music, she was confident that every muse would recognize themselves in her lyrics.

"They're all made very clear," Swift said. "Every single song is like a roadmap to what that relationship stood for, with little markers that maybe everyone won't know, but there are things that were little nuances of the relationship, little hints. And every single song is like that."

"Dear John" is the most obvious example, likely owing its title to Swift's ex John Mayer (though it also doubles as a reference to a wartime breakup letter, historically sent from a woman to a soldier).

Indeed, the tabloid fodder attached to "Dear John" may have threatened to eclipse the song's power, had 20-year-old Swift been a less capable songwriter.

"It might seem sensationalistic to focus on 'Dear John' at the expense of the rest of the album if it didn't feel like it might be her masterpiece to date, or at least the most bracingly, joltingly honest song you've heard any major performer have the nerve to put on record in years," Willman wrote in his review of "Speak Now," comparing the rock-infused takedown to John Lennon's "How Do You Sleep."

"But while Lennon's song came off as mean-spirited," Willman continued, "Swift was motivated by vulnerability and woundedness, which makes her song far braver... and more cutting."

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1. "All Too Well (10 Minute Version)"

1. "All Too Well (10 Minute Version)"
"All Too Well (10 Minute Version)" is the 30th track on "Red (Taylor's Version)."John Shearer/Getty Images for TAS Rights Management

"All Too Well" remained a pet favorite among Swifties for nearly a decade. When I ranked it as the fifth-best song of the 2010s, I distinctly remember friends (who were unfamiliar with Swift's deep cuts) reaching out to ask, "Really? This one?"

"Red (Taylor's Version)" offered long-awaited vindication. Thanks to a brilliantly targeted promotional campaign, complete with a Grammy-nominated short film and norm-breaking performance on "Saturday Night Live," Swift's 10-minute power ballad is finally known far and wide as her greatest work to date.

Few artists could admit to being maimed in the name of love and emerge stronger than ever — elegantly, triumphantly intact.

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