The Most Heartbreaking Songs and Lyrics From Taylor Swift’s Tortured Poets Department

If there’s one artist you can trust to write lyrics that read like absolute poetry for the most heartbreaking songs, it’s Taylor Swift, who has done just that with the release of The Tortured Poets Department. Grab your tissues and prepare for all your trauma to resurface; you can do it with a broken heart. 

It would be pointless to deny this, and so we won’t: While it is unquestionably an incredible feat of lyrical and melodic wonder, The Tortured Poets Department: The Anthology can also be both overwhelming and excessive. While the initial album was presented as having 16 tracks, the 2AM release of The Anthology gave us an additional 15, bringing the total up to 31 tracks and a runtime of 2 hours and 2 minutes.  

Even for seasoned Swifties, that’s a lot of Taylor. 

Taylor Swift’s The Tortured Poets Department faces harsh critique, but is the hate justified? 

When Taylor Swift dropped the 2AM version of The Tortured Poets Department, Swifties the world over had already exhausted their emotions weeping over the first 16 songs. An additional 15 tracks meant more time was needed to process the masterpiece, with hours given to first plays, replays, and post-mortems involving topics like ‘Is this a Joe or a Matty?’, and ‘Did Jack or Aaron write this?’.  

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A post shared by Taylor Swift (@taylorswift)

In the face of Swift’s immediate success with The Tortured Poets Department, which garnered 300 million streams on Spotify on its first day, popular media and music reviewers were quick with their criticisms — some fair, most unfounded. 

This struck us (and many Swifties) as odd. The reviews hit the internet mere moments after the album(s) were released, leaving barely enough time for a proper listen, let alone a comprehensive deep dive into the album’s inspirations, meanings, and the depth of feeling its production certainly must have required. 

Can’t get over the @nytimes writing about Taylor Swift “fatigue” when this….. is the NYT. Bitch get mad at yourself!!! pic.twitter.com/oe0OUcGgfx

— Lynds (@lynds_ms) April 23, 2024

While it goes without saying that The Tortured Poets Department has certainly earned its fair share of glowing acclaim, it has also garnered reviews as dismissive and scathing as the lyrics to The Smallest Man Who Ever Lived. Media critics drew attention to the oversaturation of Swift news in the entertainment industry; in that same breath, these same critics capitalised on her star power and popularity to rake in clicks and advertising dollars. 

“Critics/NYT/Media”: There’s Taylor Swift Fatigue. She’s “over-exposed”. There’s two many songs, a double album is too much.

Meanwhile, actual Swifties: pic.twitter.com/nSSjNobZ6y

— Polska_Peach (@PolskaPeach) April 23, 2024

Others applied a more practical approach to their critique, opining on the quality of Swift’s songwriting and whether her collaborative partnership with longtime friend and producer Jack Antonoff had passed its expiration date. And though it is perfectly acceptable to find the album lacking, a small collective of individuals with questionable reading comprehension skills have since emerged to find fault with Swift’s lyrics for I Hate It Here, painting them as insensitive and offensive — more on that later. 

We will, however, say this: It is impossible to form an illuminated opinion of Leonardo da Vinci’s artistic prowess after a 2-second glimpse of the Mona Lisa. 

By that logic, it certainly bears merit to consider that The Tortured Poets Department deserves more than a much-skipped and hurried-through listen for the sole intent of producing a contrary, scathing review. Because let’s face it: More than anyone, Swift is aware of the criticism that follows her excellence. And one thing is made clearer than day in The Tortured Poets Department. 

You don’t have to like her life’s work or music. But credit where credit is due means that Swift deserves praise for the hard work she’s put into building a legacy that nobody (not even the mysterious Aimee) can tear down. 

We, however, absolutely love The Tortured Poets Department and everything it stands for. 

Everything we loved about The Tortured Poets Department 

On first listen, The Tortured Poets Department came off as a long-winded compilation of seemingly unrelated words that went on and on and on. However, consequent replays led us to one simple understanding: If you’ve ever had your heart broken, its sultry odes and wistful recollections are balm for the soul. 

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With every listen, we found ourselves diving deeper into Swift’s psyche, the songstress’ masterful storytelling capabilities inviting us into the realm of her imagination. On display: Her life’s story, her battles with mania and depression, her romantic afflictions, and the desolation that comes from being simultaneously the loneliest, as well as the most famous person in the world.  

Iconic Swiftie Moments During TTPD release week – a thread. pic.twitter.com/A2UFUY1r0w

— ray (@styledinred) April 25, 2024

Through the lyrics and songs of The Tortured Poets Department, Taylor Swift spins a heartbreaking tale of being worn out and stretched thin, and yet having to perform whilst hiding her true feelings from a world intent on scrutinising her every move. The resultant tracks are vulnerable and relatable, providing an in-depth look into the superstar’s life in a way that her previous albums have never done. 

In The Tortured Poets Department, Swift, fully realised as a powerful entity of the entertainment industry, stands tall and proud as if to say, “Here I am. This is me. If you love me, love all of me — even the parts that are scared and dark and lonely.” 

it’s taken over my life pic.twitter.com/MpZmiX5UJ2

— lauren (@gilmxres) April 22, 2024

Despite certain obtuse individuals who insist on misinterpreting Swift’s lyrics, we’re glad we forged ahead through the album, giving it the chance to grow on us. And grow on us it has, eking out fresh emotion and new realisations with every listen. 

In view of that, here are our picks for some of the most heartbreaking songs and lyrics from Taylor Swift’s Tortured Poets Department. 

The most heartbreaking songs and lyrics from Taylor Swift’s Tortured Poets Department 

Fortnight (feat. Post Malone) 

The leading single from The Tortured Poets Department is a mellow introduction to the rest of the album. Sung alongside Austin Post, the track details life in the aftermath of a breakup, with Swift reflecting on the unHealthy nature of her previous, now passed relationship.  

In the song, Swift relegates the fleeting experience to memory, whilst acknowledging the dreary and listless emotions that accompany newly single life. She sings, “All my mornings are Mondays / Stuck in an endless February / I took the miracle move on drug / The effects were temporary / And I love you, it’s ruining my life / I love you, it’s ruining my life.” 

The Tortured Poets Department 

This track cuts deep if you’ve ever stayed too long in an unhealthy relationship. With an undercurrent of deep denial and refusal to see the truth, Swift writes about a lover with self-destructive tendencies. In the same breath, she expresses her commitment and loyalty, echoing the sentiment that love will conquer all with the lyrics, “But you awaken with dread, pounding nails in your head / But I’ve read this one where you come undone / I chose this cyclone with you.” 

My Boy Only Breaks His Favourite Toys 

In a similar vein of denial, My Boy Only Breaks His Favourite Toys follows up from The Tortured Poets Department. The third track of the album details the feeling of confusion that comes after the ‘honeymoon’ period of any budding relationship. In a commentary for Amazon Music, Swift shares that the track was inspired by that feeling of ‘being somebody’s favourite toy until they break you, and then don’t want to play with you anymore.’ 

Swift goes on to elaborate, “Which is how a lot of us are in relationships where we are so valued by a person in the beginning, and then all of the sudden, they break us or they devalue us in their mind. We’re still clinging on to ‘No no, no. You should’ve seen them the first time they saw me. They’ll come back to that. They’ll get back to that.’” 

In the song, Swift likens herself to a plastic doll, highlighting how shiny and new she once felt with lyrics that read, “The sickest army doll / Purchased at the mall / Rivulets descend my plastic smile / But you should’ve seen him / When he first got me.” Drawing a sharp comparison to the beginning, Swift later goes on to end the song with, “Cause he took me out of my box / Stole my tortured heart / Left all these broken parts / Told me I’m better off / But I’m not.” 

So Long, London 

The fifth song in The Tortured Poets Department is also one of the most heartbreaking, with lyrics that speak of despair at a failed long-term relationship. Widely agreed-upon as Swift’s emotional, yet dignified adieu to her six-year relationship with ex Joe Alwyn, So Long, London, is a heartfelt, mournful ballad that stirs the depths of the soul. Mellow vocalisations recalling church bells and Swift’s sultry tones are layered over a frenetic, fluttering heartbeat, contrasting the steady, sorrowful beats of You’re Losing Me. 

As expected, the song details Swift’s deep melancholy, with tinges of anger bursting forth. Swift reflects on her past relationship, her role in keeping it alive, and how the burden eventually grew too heavy to bear, singing, “My spine split from carrying us up the hill / Wet through my clothes, weary bones caught the chill / I stopped trying to make him laugh / Stopped trying to drill the safe.” 

Swift also alludes to feeling unseen and unheart, highlighting her fears of cheating in the bridge, “My friends said it isn’t right to be scared / Every day of a love affair / Every breath feels like rarest air / When you’re not sure if he wants to be there / So how much sad did you think I had / Did you think I had in me? / How much tragedy?”  

Yet, most heartbreaking of all are these lyrics, which truly hammer in how alone Swift must have felt as she penned, “You swore that you loved me but where were the clues? / I died on the altar waiting for the proof.” 

Who’s Afraid Of Little Old Me 

An extraordinary commentary on the life of a celebrity, Who’s Afraid Of Little Old Me details Swift’s journey into superstardom, highlighting its most unpleasant aspects. Through the lyrics, Swift narrates her experiences as a successful woman in the entertainment industry, pointing to unfounded criticism surrounding everything from her personal life to her music. 

Alluding to those who would use her for their own gain, Swift sings, “The who’s who of who’s that? / Is poised for the attack / But my bare hands paved their paths.” Swift then goes on to address the effects of unbridled judgment, recalling the sass of Reputation’s I Did Something Bad (They’re burning all the witches even if you aren’t one). Expanding on the effects of bullying, she then sings, “Is it a wonder I broke? Let’s hear one more joke / Then we could all just laugh until I cry.” 

Further calling out the harsh realities of the entertainment industry, Swift goes on to sing, “I was tame, I was gentle ’til the circus life made me mean / Don’t you worry folks, we took out all her teeth / Who’s afraid of little old me?” before finally concluding the song with the bridge to end all bridges: “… I wanna snarl and show you just how disturbed this has made me / You wouldn’t last an hour in the asylum where they raised me / So all you kids can sneak into my house with all the cobwebs / I’m always drunk on my own tears, isn’t that what they all say?” 

loml 

In the mournful ballad that is loml, Swift addresses both the great loves and losses of her life, perfectly integrating her heartbreaking lyrics into the gentle notes of her piano. Speaking to anyone who has ever been despaired in love, the singer details a beautiful romance soured by deceptions and disappointments. While fans are divided as to whether the song is meant for Joe Alwyn or Matty Healy, its meaning remains the same: love is treacherous and all too easily lost. 

Swift alludes to the feeling of waking up to reality, singing, “Who’s gonna tell me the truth / When you blew in with the winds of fate / And told me I reformed you / When your impressionist paintings of Heaven / Turned out to be fakes / Well, you took me to hell, too.” She goes on to add, “Oh, what a valiant roar / What a bland goodbye / The coward claimed he was a lion / I’m combing through the braids of lies / ‘I’ll never leave’ … / ‘Never mind’.” 

And most heartbreakingly, Swift once again speaks of her desire to marry her lover, but is rebuffed by his behaviour towards her. “You sh–t talked me under the table / Talking rings and talking cradles / I wish I could un-recall / How we almost had it all.” 

I Can Do It With A Broken Heart 

This track is the perfect anthem for those who find themselves living with affliction of high-functioning depression. In this catchy track, which bears all the hallmarks of Jack Antonoff’s synth-pop production, Swift gives us all a peek into her life in the earliest days of her groundbreaking Eras tour. With her career on the line, Swift drew from the deepest recesses of strength and put on amazing shows, night after night — with nary a thought for heartbreak. 

She sings, “‘Cause I’m a real tough kid, I can handle my shit / They said, baby, gotta fake it ’til you make it and I did / Lights, camera, b–tch smile, even when you wanna die / He said he’d love me all his life / But that life was too short / Breaking down, I hit the floor / All the pieces of me shattered as the crowd was chanting, ‘More!’.” Further driving home the strength it must have taken to pull off the tour, Swift goes on to add, “I cry a lot but I am so productive, it’s an art / You know you’re good when you can even do it / With a broken heart.” 

The Smallest Man Who Ever Lived 

In this scathing dedication to Matty Healy, (who is the smallest man in the world, if Swift’s lyrics are to be believed) the songstress explores the agony of being abruptly abandoned in the early days of a budding relationship. Swift provides a glimpse into her deep feelings, yet acknowledges that the man will likely get away with wasting her time and breaking her heart, singing, “I would’ve died for your sins / Instead I just died inside / And you deserve prison but you won’t get time.” 

The Black Dog 

Yet another bitterly heartbreaking poem disguised as a tender ballad, The Black Dog echoes with denial following the earliest days of separation. Swift sings of a lover who has forgotten to turn off location sharing, and so watches him walk into a pub called The Black Dog. The lyrics likewise convey her feelings, with, “I move through the world with the heartbroken / My longings stay unspoken”, and “You said I needed a brave man / Then proceeded to play him / Until I believed it too.” 

How Did It End 

In How Did It End, Swift contemplates the cycle of gossip that surrounds heartbreak and breakups. She elucidates her thoughts on the subject through heartfelt lyrics that seem to pay little heed to the pain of those personally involved, likening the desire to gossip to an empathetic hunger. Mournfully, she regales the listener with a tale of two lovers drifting apart, with, “He was a hothouse flower to my outdoorsman / Our maladies were such we could not cure them,” and “We learned the right steps to different dances / And fell victim to interlopers’ glances.” 

Swift goes on to express the pains of losing a longtime lover, singing, “Say it once again with feeling / How the death rattle breathing / Silenced as the soul was leaving / The deflation of our dreaming / Leaving me bereft and reeling.” 

I Hate It Here 

In this (unfairly) polarising track, Swift sings of how nostalgia is the mind’s trick. In the lyrics, she goes on to express that she hates where she is in life, and so escapes to the gardens in her mind. Her lyrics have sadly raised the ire of some, who took issue with the lines, “My friends used to play a game where / We would pick a decade / We wished we could live in instead of this / I’d say the 1830s but without all the racists and getting married off for the highest bid.” The criticism was that Swift came off blithely unaware of the other issues surrounding the 1830s, from rampant racism and slavery to disease and other unpleasant things. 

Yet, Swift would go on to indicate her awareness that every era has its darkest days, singing, “Everyone would look down / Cause it wasn’t fun now / Seems like it was never even fun back then.” As some Swifties have also pointed out, 1830 was the year that famed poet Emily Dickinson was born; it was also the ‘romantic’ era for poets and poetry, two facts which have likely informed the lyrical decision.

Through her other lines in the song, Swift elucidates that she would much rather live within her imagination, singing, “I’ll save all my romanticism for my inner life and I’ll get lost on purpose,” and “I hate it here so I will go to / Secret gardens in my mind.” 

The Prophecy 

The Prophecy is for all the hopelessly romantic, and yet eternally single folk who have felt the brunt of heartbreak in their loneliness. In this song, Swift sings of feeling excitement for the first blooms of love, only to be disappointed yet again. Believing herself cursed in her darkest moments, she sings, “But I looked to the sky and said / Please / I’ve been on my knees / Change the prophecy / Don’t want money / Just someone who wants my company / Let it once be me.” 

These lyrics are certain to resonate with those who have experienced such heartbreak. In true display of her mastery with words, Swift goes on to add, “And I sound like an infant / Feeling like the very last drops of an ink pen / A greater woman stays cool / But I howl like a wolf at the moon,” highlighting her desperation to simply be loved for who she is. 

The Manuscript 

Closing off The Tortured Poets Department and rounding off the torrid love affairs of her past, Swift makes it clear in The Manuscript that she is ready to move on. Sung along to gentle piano notes and a resonant background hum, the song perfectly elucidates the feeling of starting anew after a failed relationship. In The Manuscript, Swift tells us that she is cognizant of the past she will always share with those whose paths she has crossed; yet, she is ready for the future. 

The lyrics are suffused with a tender determination, as Swift sings, “The only thing that’s left is the manuscript / One last souvenir from my trip to your shores / Now and then I re-read the manuscript / But the story isn’t mine anymore.”

(Main and featured image: Taylor Swift/Instagram)

Frequently Asked Questions (FAQs) 

– What is Taylor Swift’s saddest song? 

Taylor Swift has many sad songs, particularly in The Tortured Poets Department and The Anthology. Among them are So Long, London, loml, How Did It End, The Prophecy, and I Can Do It With A Broken Heart, among others. 

– Is Tortured Poets Department a good album? 

While reviews have been divisive at best, The Tortured Poets Department has shattered streaming records, and is the fastest album to reach 1 billion streams within a week. But don’t take our word (or anyone else’s!) for it; give it a listen and formulate an opinion you can call your own. 

– What is the single from The Tortured Poets Department? 

The leading single from The Tortured Poets Department is Fortnight (feat. Post Malone).  

– Are there any happy songs on TTPD? 

Two songs on TTPD are seemingly about Travis Kelce, who is Taylor Swift’s current boyfriend. These are quite happy and signify better times for the singer, who has not been the luckiest in love.