One year ago, Taylor Swift released her highly anticipated album The Tortured Poets Department. This album arrived like a letter, carefully sealed and stained with ink, pulled from the drawer of a haunted typewriter. The Tortured Poets Department was like a confession, a collection of unsent letters and unspoken thoughts wrapped in velvet melancholy and typewriter clacks. For fans of dark academia, the album became a soundtrack for quiet, reflective moments—when the world is too loud and your thoughts feel too heavy.

As we celebrate the first anniversary of this deeply personal collection, we invite you to reflect, feel, and embrace the darkest corners of your mind. So pour a drink, light a candle, and let these songs take you through the labyrinth of thought, passion, and unspoken longing. Here is a small analysis of my favorite songs from the album.

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I Hate It Here

This song is special to all of my creative people out here. It perfectly encapsulates the angst of finding yourself in a place you should belong, yet feeling more alienated with every passing second. It is about not being able to find a home, the place where you feel safe and understood. So you create a world of imagination and drown yourself in the illusions of moments that never happened.

This song is an anthem for the isolated intellectual, struggling between pages of unread books. It is a fundamental piece of the album because the story starts with a poet creating a world of fantasy, which cannot be touched by the shallowness of the world.

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Down Bad

We all know what "down bad" means. It's that painfully relatable condition where someone is hopelessly, often embarrassingly, deep in their feelings — usually about another person who may or may not even know they exist. This song is a perfect soundtrack for the nights when you cannot tell if you are living or dreaming.

Describing the meaning behind the song in her iHeartRadio listening party for The Tortured Poets Department, Taylor said, "The metaphor in ‘Down Bad’ is that I was comparing a sort of the idea of being love-bombed. Where someone… rocks your world and dazzles you and then just abandons you." She continued, "This girl is abducted by aliens but wanted to stay with them… and then when they drop her back off in her hometown, she’s like, ‘Wait, no, where are you going? I liked it there! It was weird, but it was cool. Come back’!"

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Guilty as Sin

We are all guilty of something. Perhaps it's a thought too dark, a word left unsaid, or a mistake repeated too many times to count. In this song, the narrator is bored, yearning, and lost in fantasy over someone. Taylor grapples with whether she should feel guilty for something that’s never actually happened—hence the question mark in the title.

There is something so relatable about this song—when the line is blurred between the fantasy and reality. It’s not just about doing wrong—it’s about wanting something you know you shouldn’t. If you’ve ever loved too fiercely or lived too recklessly, this song is your confession, your elegy.

Fresh Out the Slammer

This song is what I call "a celebration of breaking from chains''. It is about wanting and choosing freedom, not caring about the weights of the past anymore. It’s that feeling of stepping out of something that nearly broke you—and realizing you’re still standing.

Taylor comes across as a little bruised, a bit jaded, but undeniably free. The song reflects that—it’s messy, gritty, and unapologetically raw.

Yet, the second she’s free, she’s already looking for that same thrill again. That contradiction—wanting peace but chasing intensity—feels central to the tortured poet archetype. It's about relapse, rebound, and the refusal to learn from the past because love, even when it ruins you, feels like purpose.

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I Can Fix Him, No Really, I Can

This is one of the most satirical songs on the album, but it cuts deep because of how relatable it is. It satirizes the naive belief that love can fix the unfixable. Taylor channels the voice of someone clinging to the idea that her love can redeem, despite all the red flags.

The song is clever but also a little tragic—because underneath the sarcasm is a real vulnerability. It captures the quiet desperation of wanting to be the exception, of believing that your love story will defy the odds, even when every sign says otherwise. There's a wink in the delivery, but there's also a sigh. Taylor knows this pattern, knows how it ends, but sings it anyway—like a warning wrapped in a love letter.

Loml

The phrase “Loml”—or "Love of My Life"—has never sounded more bittersweet than it does in this song. It speaks to a love that exists only in the margins of dreams, one that is both all-consuming and inevitably doomed. It’s the perfect track for those moments when you’re falling for someone who could never love you back—or worse, someone you know will ruin you.

This song is structured like a soft love letter until it isn’t. What begins as reverence transforms into quiet devastation as the meaning of “love of my life” shifts into “loss of my life. This song is sad because Taylor not only mourns the relationship but also the time spent believing it was real and the parts of herself she gave away in the name of forever. It’s profoundly adult in its realization that sometimes, the biggest heartbreaks are the quietest.

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How Did It End?

This song is one of the softest, most emotionally unsettled songs on The Tortured Poets Department. It’s not a ballad of love or fury; it’s a song made entirely of fog—of questions that come too late and answers that never arrive. Unlike Taylor’s songs that deal with clear betrayal or heartbreak, "How Did It End?" lives in the murky in-between.

It’s not about someone leaving in the middle of the night or a love turned to poison. It’s about the quiet death of a connection—the kind that dies slowly, without a bang. So slowly that by the time you notice, it’s already over. It’s for anyone who’s ever found themselves at a dead end, staring into the void, wondering what went wrong.

The Smallest Man Who Ever Lived

And here comes the anger in every story. This song isn’t about heartbreak. It’s about the moment after—when the sadness has burned off and what’s left is clarity, embarrassment, and a simmering rage.

Taylor doesn’t just mourn the relationship here; she dismantles it. Piece by piece. She turns the spotlight on someone who once had power over her and sees him for what he truly is: not a larger-than-life man, but a tiny, insecure, and performative man.

If we think about the context of the album, “The Smallest Man Who Ever Lived” sits at a turning point. It follows the quieter grief of "How Did It End?" and precedes the mythic isolation of "Cassandra." Here, we see Taylor pulling herself out of sorrow and sadness. She stops mourning the fantasy and starts naming the reality. And it’s powerful.

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Cassandra

Cassandra, the cursed prophet who was never believed, is a symbol of Taylor herself: constantly ahead of the curve, trapped in a cycle of knowing the truth and never being heard. This song takes on the despair of seeing the world with clarity while everyone else stumbles blindly towards it. It’s a track that will resonate with those who’ve known the painful loneliness when you are never heard.

Taylor’s delivery is soft, almost ghostly. Taylor knows that no matter what she says, she’ll be ignored again. The production mirrors this: murky, slow-burning, and trance-like. There’s no climax, no dramatic explosion—just the sadness of being tossed aside every time you raise your voice.

The Prophecy

And here it is, my favorite song by Taylor Swift. There is something so relatable about this song—when you are so desperate to change your destiny, not fulfill the painful prophecy. There’s no mask in this song. There is no satire, performance, or mystery. Just a simple, heartbroken question: “Was I destined for loneliness?”

After all the fun and pain of the failed relationships, there comes a spiritual sadness in the narrator. She’s not trying to manifest anything anymore. She’s just asking for clarity, just a sign that everything will be okay.

In this song, Taylor distills a feeling that so many of us have had but rarely admit out loud: maybe the world isn't cruel, exactly. Just... indifferent.

So there you have it—The Ultimate Dark Academia Playlist for Fans of The Tortured Poets Department. Which of these songs is your favourite?