Taylor Swift's 15 best breakup songs, ranked

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.

Highlight verse:

I'm scared to see the ending
Why are we pretending this is nothing?
I'd tell you I miss you, but I don't know how
I've never heard silence quite this loud

"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. 

Highlight verse:

Was I out of line?
Did I say something way too honest, made you run and hide
Like a scared little boy?
I looked into your eyes
Thought I knew you for a minute

Now I'm not so sure

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."

Highlight verse:

So I'll watch your life in pictures like I used to watch you sleep
And I feel you forget me like I used to feel you breathe
And I'll keep up with our old friends
Just to ask them how you are
Hope it's nice where you are

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.

Highlight verse:

You shit-talked me under the table
Talking rings and talking cradles

I wish I could un-recall

How we almost had it all

Dancing phantoms on the terrace

Are they secondhand embarrassed

That I can't get out of bed?

'Cause something counterfeit's dead

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.

Highlight verse:

Took off faster than a green light, go
Hey, you skip the conversation when you already know
I left a note on the door with a joke we'd made
And that was the first day

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.

Highlight verse:

I hate that stupid old pickup truck you never let me drive
You're a redneck heartbreak who's really bad at lying
So, watch me strike a match on all my wasted time
As far as I'm concerned, you're just another picture to burn

"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."

Highlight verse:

Dreams of your hair and your stare and sense of belief
In the good in the world, you once believed in me
And I felt you and I held you for a while
Bet I could still melt your world
Argumentative, antithetical dream girl

"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.

Highlight verse:

I just don't understand
How you don't miss me in the shower

And remember how my rain-soaked body was shaking

Do you hate me? Was it hazing?

For a cruel fraternity I pledged

And I still mean it

Old habits die screaming

"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.

Highlight verse:

One for the money, two for the show
I never was ready so I watch you go
Sometimes you just don't know the answer
'Til someone's on their knees and asks you
"She would've made such a lovely bride
What a shame she's fucked in the head," they said
But you'll find the real thing instead
She'll patch up your tapestry that I shred

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.

Highlight verse:

My heart, my hips, my body, my love
Trying to find a part of me that you didn't touch
Gave up on me like I was a bad drug
Now I'm searching for signs in a haunted club
Our songs, our films, united we stand
Our country, guess it was a lawless land
Quiet my fears with the touch of your hand
Paper cut stings from our paper-thin plans
My time, my wine, my spirit, my trust
Trying to find a part of me you didn't take up
Gave you too much, but it wasn't enough
But I'll be alright, it's just a thousand cuts

"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.

Highlight verse: 

Dust collected on my pinned-up hair
I'm sure that you got a wife out there
Kids and Christmas, but I'm unaware
'Cause I'm right where I cause no harm
Mind my business
If our love died young
I can't bear witness
And it's been so long
But if you ever think you got it wrong

I'm right where
You left me

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.

Highlight verse:

Ten months sober, I must admit
Just because you're clean don't mean you don't miss it
Ten months older, I won't give in
Now that I'm clean, I'm never gonna risk it

"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.

Highlight verse:

I persist and resist the temptation to ask you
If one thing had been different
Would everything be different today?

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."

Highlight verse:

You are an expert at sorry and keeping lines blurry
Never impressed by me acing your tests
All the girls that you've run dry have tired lifeless eyes
'Cause you burned them out
But I took your matches before fire could catch me
So don't look now
I'm shining like fireworks over your sad empty town

"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.

Highlight verse:

And I was never good at telling jokes, but the punch line goes
"I'll get older, but your lovers stay my age"
From when your Brooklyn broke my skin and bones
I'm a soldier who's returning half her weight
And did the twin flame bruise paint you blue?
Just between us, did the love affair maim you too?
'Cause in this city's barren cold
I still remember the first fall of snow
And how it glistened as it fell
I remember it all too well