Taylor Swift’s 20 best breakup songs, ranked

Taylor Swift performs during the Eras Tour in Glendale, Arizona.

John Shearer/Getty Images for TAS Rights Management

Taylor Swift is known for writing exceptional breakup songs.
The best examples in Swift’s catalog include “Dear John,” “Champagne Problems,” and “All Too Well.”
Three songs from “The Tortured Poets Department” are the newest to join our top-20 ranking.

Taylor Swift has perfected the art of the breakup anthem.

Although Swift’s newest album, “The Life of a Showgirl,” is, in her words, more “flirty and fun” than much of her past work, the singer-songwriter has spent a good chunk of her career plumbing the full range of heartbreak, from regret and anger to despair, yearning, bewilderment, and even relief.

“I’m really known for a lot of my sad songs, my cathartic songs, or breakup songs or whatever, because I love to write those things,” Swift recently told Apple Music’s Zane Lowe.

The 20 best breakup songs in Swift’s discography are ranked below, in ascending order.

20. “Should’ve Said No”

Taylor Swift performs at the 2008 Academy Of Country Music Awards. — Kevin Winter/ACMA/Getty Images for ACMA

What “Before He Cheats” is to Carrie Underwood, “Should’ve Said No” is to Swift. It’s the perfect song for a post-heartbreak karaoke session, when all your friends have gathered to commiserate, trash-talk your ex, and, hopefully, raise your spirits.

As you sing along, you’ll find it’s impossible not to adopt Swift’s twangy teenage fury, or smile as she eviscerates whatever cheating scumbag crossed her path.

Despite the obvious pain in her lyrics, “Should’ve Said No” is one of the most upbeat and triumphant breakup songs in Swift’s discography.

Best lyrics:

I should’ve been there, in the back of your mind
I shouldn’t be asking myself why
You shouldn’t be begging for forgiveness at my feet
You should’ve said no
Baby, and you might still have me

19. “Better Man”

Taylor Swift performs during the Eras Tour in Miami.

TAS2024/Getty Images for TAS

Swift wrote “Better Man” alone during the original “Red” era, but instead of recording it herself, she offered the chance to Little Big Town instead.

“She sent us this song, and it was one that was really special to her,” band member Karen Fairchild revealed during a Q&A in 2016. “She thought of us because of the harmonies.”

Fairchild also said that as soon as the bandmates heard Swift’s demo, they knew they had to record it.

Their instincts were spot-on: Little Big Town’s version won song of the year at the 2017 CMA Awards and best country duo/group performance at the 2018 Grammy Awards. (It was also nominated for best country song at the Grammys, but that’s a songwriter’s award, so it would’ve been Swift’s to take home. Alas, she was beaten by Chris Stapleton.)

By the time Swift revisited “Better Man” for “Red (Taylor’s Version),” her vocals had matured enough to do the melodies and harmonies justice. Swift co-produced the updated version with Aaron Dessner, who worked his magic to bring the mournful vignette to life.

Best lyrics:

But your jealousy, oh I can hear it now
Talking down to me like I’d always be around
Push my love away like it was some kind of loaded gun
Oh, you never thought I’d run

18. “How Did It End?”

Taylor Swift performs "The Smallest Man Who Ever Lived" on the Eras Tour in Stockholm. — Taylor Swift performs “The Smallest Man Who Ever Lived” on the Eras Tour in Stockholm.

Michael Campanella/TAS24/Getty Images for TAS Rights Management

If you were to split Swift’s “The Tortured Poets Department” and its surprise second half, “The Anthology,” into two different albums, “How Did It End?” would be the latter’s track five.

Fans know that Swift tends to reserve her most vulnerable music for the fifth slot on a tracklist, and “How Did It End?” more than deserves that distinction.

Swift characterizes the song as a lovers’ autopsy, singing in the opening line, “We hereby conduct this postmortem.” She revisits this imagery in the bridge when she distorts a silly, romantic nursery rhyme into something bleak and morbid: “My beloved ghost and me, sitting in a tree, D-Y-I-N-G.”

Swift is resigned to the death of another relationship, but with that resignation comes glimpses of anger (“The empathetic hunger descends”) and even humor (“We’ll tell no one, except all of our friends”). She makes fun of the peanut gallery that’s bound to ask the titular question, ravenous for more details of her heartache, all while giving them exactly what they want. Come one, come all, indeed.

Best lyrics:

We were blind to unforseen circumstances
We learned the right steps to different dances
And fell victim to interlopers’ glances
Lost the game of chance, what are the chances?

17. “You’re Losing Me”

taylor swift midnights press photo — Beth Garrabrant

Swift surprised fans with “You’re Losing Me” during the first leg of the Eras Tour, just a few months after her split from Joe Alwyn was made public. She described the loosie as a vault track from her then-new album, “Midnights.” The song’s cowriter and co-producer, Jack Antonoff, later confirmed it was written in December 2021.

The lyrics of “You’re Losing Me” chronicle the drawn-out demise of a long-term relationship. Swift is tormented by her own indecision, but more so by her lover’s apathy.

In the bridge, Swift pleads with him to change his tune, to convince her to stay, to do or say anything at all. “Choose something, babe, I got nothing to believe,” she sings, “Unless you’re choosing me, you’re losing me.”

Swift refuses to admit she’s already been lost, and if Antonoff’s timeline is any indication of the song’s real-life roots, she would remain in denial for another few years.

“You’re Losing Me” is the musical equivalent of romantic purgatory. Anyone who’s been in a similar situation can see the writing on the wall.

Best lyrics:

Fighting in only your army
Frontlines, don’t you ignore me
I’m the best thing at this party
And I wouldn’t marry me either
A pathological people pleaser
Who only wanted you to see her

16. “Forever & Always”

taylor swift fearless tour — Taylor Swift performs at Madison Square Garden on August 27, 2009.

Theo Wargo/WireImage

“Forever & Always” was the final song Swift wrote for the original version of “Fearless. ” Shortly before the album was finalized, she went through her first public breakup, and she said she begged her former label head, Scott Borchetta, to allow the last-minute addition.

By that point, “Fearless” already boasted an array of breakup anthems, from “White Horse” and “Breathe,” featuring Colbie Caillat, to “Tell Me Why” and “You’re Not Sorry.”

Still, as strong as that track run is, “Forever & Always” injects a much-needed sense of urgency and petulance that clarifies the album’s feisty teenage spirit.

“It’s about watching somebody fade away in a relationship,” Swift told the Los Angeles Times of “Forever & Always” in 2008. “That emotion of rejection, for me, usually starts out sad and then gets mad. This song starts with this pretty melody that’s easy to sing along with, then in the end, I’m basically screaming it because I’m so mad.”

It’s true that “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 memories. 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.

Best lyrics:

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

15. “The Story of Us”

taylor swift 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 with 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.

Best lyrics:

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

14. “Hits Different”

taylor swift eras tour — Taylor Swift performs during the Eras Tour in Las Vegas.

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 laying it all on the table, and she’s not embarrassed one bit.

The bridge is particularly 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.”

With every memory that flashes through her mind, every artifact that she rediscovers in a drawer, Swift loses her grip just a little bit more. Rarely has a downward spiral sounded so fun.

Best lyrics:

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

13. “Last Kiss”

taylor swift speak now tour — Taylor Swift performs during the Speak Now World Tour at Madison Square Garden.

Larry Busacca/Getty Images

The release of “Speak Now” marked a distinct period of growth in Swift’s life. As Jon Caramanica wrote for The New York Times, her first two albums were partially cloaked in daydreams and the delusions of 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 bruises of lived-in places, beating hearts, and warm clothes. Even the title evokes an intimate touch, a lingering tingle, which Swift deploys in the song’s final moments to leave the listener wanting more — just as she’s been left wanting more.

Best lyrics:

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
And I hope the sun shines and it’s a beautiful day
And something reminds you, you wish you had stayed
You can plan for a change in the weather and time
But I never planned on you changing your mind

12. “Loml”

Taylor Swift performs during the Eras Tour. — Vittorio Zunino Celotto/TAS24/Getty Images

It’s difficult to pick the best breakup track from “The Tortured Poets Department,” Swift’s self-described “manic phase” of an album, even just from the 16-track standard edition.

“So Long, London” (a slow-burn collapse), “The Smallest Man Who Ever Lived” (a scathing takedown), or even “I Can Do It With a Broken Heart” (a satirical ode to smiling through the pain) would be worthy picks for an all-time ranking.

But “Loml” stands out as the album’s most harrowing chapter. 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.” 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 momentary to legendary.

Best lyrics:

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

11. “Is It Over Now?”

taylor swift 1989 taylor's version press photo — Taylor Swift in a promo photo for “1989 (Taylor’s Version).”

Beth Garrabrant

The fifth and final vault track on “1989 (Taylor’s Version)” is a sugar rush of pop synths, stuttering drum beats, bitter accusations, and self-destructive confessions. It’s hard to pull off high-tempo misery, but Swift does in this song.

Swift has described “Is It Over Now?” as a companion to “Out of the Woods” and “I Wish You Would,” a pair of pop bangers from the original “1989” tracklist.

Like those songs, “Is It Over Now?” is the product of an obsessive back-and-forth romance that never feels quite finished. It’s the antithesis of closure. But unlike those songs, “Is It Over Now?” fully embraces the frenzy that sometimes comes with wanting someone that much. Swift even admits to fantasizing about “jumping off of very tall somethings,” not to die, but to convince her ex to run back to her bedside.

By releasing “Is It Over Now?” in 2023, a decade after its writing, the song’s life cycle mirrors the same urge captured in its lyrics: to take every opportunity to stir up some drama; to never let anything stay “over” for long.

Best lyrics:

Let’s fast forward to 300 awkward blind dates later
If she’s got blue eyes, I will surmise that you’ll probably date her
You dream of my mouth before it called you a lying traitor
You search in every model’s bed for something greater, baby

10. “Picture to Burn”

taylor swift picture to burn music video — “Picture to Burn” was released as a single in 2008.

Taylor Swift/YouTube

It’s well documented that Swift inspired a new generation of songwriters, but “Picture to Burn” should have its own monument in her new republic. Grammy winner Olivia Rodrigo and Eras Tour opener 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 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.

Best lyrics:

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

9. “Holy Ground”

Taylor Swift performs during the "Red" tour. — Christie Goodwin/TAS/Getty Images

Swift’s fourth album is packed with tearjerkers and hit singles (“Red,” “I Knew You Were Trouble,” “We Are Never Ever Getting Back Together”) that capture the confusion and anguish immediately following a breakup. “Red (Taylor’s Version),” with its nine additional vault tracks, is even more so (“Better Man,” “I Bet You Think About Me,” “The Very First Night”).

But in both cases, the high-octane “Holy Ground” leaps 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 in the song 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.

Best lyrics:

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

8. “The Black Dog”

Taylor Swift performs during the Eras Tour in New Orleans.

Erika Goldring/TAS24/Getty Images for TAS Rights Management

“The Black Dog” is the first track to introduce the second half of “Poets.” It’s also one of five songs on the double album solo-written by Swift, alongside other heartbreakers like “Peter” and “The Manuscript,” which makes sense because its storytelling 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 personal tragedies into sacred ground.

Best lyrics:

Six weeks of breathing clean air, I still miss the smoke
Were you making fun of me with some esoteric joke?
Now I wanna sell my house and set fire to all my clothes
And hire a priest to come and exorcise my demons
Even if I die screaming
And I hope you hear it

7. “Champagne Problems”

Taylor Swift performing during the Eras Tour in Gelsenkirchen, Germany. — Andreas Rentz/TAS24/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 whispers and rumors of her madness behind closed doors.

In reality, Swift’s narrator isn’t mad. Her headstrong independence — her unsuitability for this particular domestic dream — lives alongside her remorse and nostalgia. 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.

Best lyrics:

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

6. “Death by a Thousand Cuts”

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 later on this list.)

The film’s protagonist, Jenny (Gina Rodriguez), is forced to reckon with the end of her nine-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 ambiguous 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.

Best lyrics:

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
Papercut 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

5. “Right Where You Left Me”

“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.”

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” isn’t an option.

“Right Where You Left Me” is Swift’s most acute illustration of yearning. She allows the dust to settle over her body and 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.

Best lyrics:

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
You left me no, oh, you left me no
You left me no choice but to stay here forever

4. “Clean”

taylor swift 1989 tour — Taylor Swift performs during the 1989 World Tour in Shanghai, China.

Liu Xingzhe/Visual China Group via Getty Images

As I have previously written, “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.

Best lyrics:

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

3. “The 1”

Taylor Swift performs "The 1" on the Eras Tour in France. — Taylor Swift performs “The 1” on the Eras Tour in France.

John Shearer/TAS24/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.

Best lyrics:

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

2. “Dear John”

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 road map 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 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.”

“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.”

Best lyrics:

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

1. “All Too Well (10 Minute Version)”

“All Too Well” remained a cult 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 masterpiece is finally known far and wide as her greatest work to date. It’s also the longest No. 1 hit in the history of the Billboard Hot 100.

Few artists could admit to being maimed in the name of love — in excruciating detail, mind you — and emerge stronger and more powerful than ever.

Best lyrics:

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

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