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Attempting to rank the 10 most tortured and most poetic songs in Taylor Swift’s ‘The Tortured Poets Department’

Love it or hate it, 'Tortured Poets' leaves a mark.

Taylor Swift performs at Accor Stadium on February 23, 2024 in Sydney, Australia. (Photo by Don Arnold/TAS24/Getty Images for TAS Rights Management)
Photo by Don Arnold/TAS24/Getty Images for TAS Rights Management

The Tortured Poets Department is Taylor Swift‘s most personal album yet, but it’s also her densest – the latter trait found commonly among critiques of it.

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It’s a fair assessment, considering there is an unusually large number of songs to get through, and Taylor has so much to say in every single one of them. Still, I argue that if there is an album where this approach works is in Tortured Poets. The title accurately sets the stage for the album’s themes of pain and extreme disillusionment, as well as the form and style of lyrics that find the pop star at her most complex and introspective.

It’s an album less concerned with palatability or easy listening and more occupied with catharsis. It feels and sounds like Taylor made it for one person only: herself. It might not resonate widely for now, but it’s easy to imagine a future where it will slowly become recognized as her best work.

10. “The Black Dog”

The Tortured Poets Department is the closest Taylor has ever been to making a rock record and “The Black Dog” is a big example of that. This gem is found among the many (and oft-superior) bonus tracks and it’s as devastating as the majority of its peers.

Taylor weaves a narrative from an unassuming starting point: an old flame forgot to turn off the location-sharing on their phone, so the singer can still see where they’re going. This leads her to wonder if that person ever misses or thinks about her during those random moments in their day. The lyrics are filled with resentment and all the more piercing thanks to Taylor’s expressive, emotion-driven vocals. This is also one of the only places on the album where Jack Antonoff displays some exciting novelty in his style of producing.

9. “Clara Bow”

Nothing hits as hard as when Taylor Swift uses her songs to reflect on her legacy and the general position of the female star in the music industry. She’s done it before in “The Lucky One,” “Nothing New,” “Castles Crumbling,” and more. “Clara Bow” is a continuation of those themes.

The song feels like it was born from conversations with Stevie Nicks, who happens to be featured in the physical copies of the CD with a poem dedicated to Taylor that highlights just how similar some of their experiences have been. The lyrics, chronologically organized, parallel Stevie’s experiences with fame with Taylor’s and with a third up-and-coming protegé who will succeed them (Olivia Rodrigo instantly springs to mind). All of them are told they look like a previous idol who was the staple of authenticity back then and “not like all those other girls are now,” that they’re different and “the real deal,” but that’s only until someone else comes along.

8. “So Long, London”

The fifth tracks on any of Taylor Swift’s albums are always expected to be particularly hard-hitting, so “So Long, London” was immediately one of the most anticipated Tortured Poets tracks when it was announced, and it did not disappoint.

The song functions as an autopsy of a dead relationship — presumably the one she shared with Joe Alwyn that involved moving to London for many years. The lyrics exemplify Taylor at the top of her game, utilizing the tools she has always relied on to their maximum potential. The word plays, the vivid storytelling, the intimacy, the crushing one-liners — it’s all there.

7. “I Hate It Here”

Arguably one of the most misunderstood tracks on Tortured Poets, “I Hate It Here” details Taylor’s fantasy worlds and how she uses them to escape a recurringly disappointing reality. Not only is this song one of the most melodically captivating on the album, it’s also one of its most relatable.

One of the defining traits of Taylor Swift’s songwriting is how she manages to be specific and universal in equal measure, and “I Hate It Here” is an excellent sample of that. We can all relate to her need for escapism, whether that’s through nostalgia, secret gardens, or the moon — we all run away to places in our minds when life gets to be too much.

6. “But Daddy I Love Him”

Imagine a song from Taylor’s Fearless album, except she’s breaking free from the jail of people’s expectations, calling her fans “judgemental creeps,” and seemingly joking about having Matty Healy’s baby just to screw with the listener. That’s “But Daddy I Love Him” — the most provocative song on Tortured Poets that deals head first with the mess that was Swiftie-dom back in May of 2023 when fans launched a campaign to force the singer into a break-up with the The 1975 frontman.

No one expected Taylor to be this direct about the issue, perhaps skirting around it not to upset her fandom, but it feels refreshing that she’s standing her ground and making sure they know “[her] good name is [hers] alone to disgrace.” Someone who was once a “pathological people pleaser” makes a definitive statement about boundaries. It’s shocking, it’s memorable, and it’s a turning point in the musician’s public persona.

5. “Chloe or Sam or Sophia or Marcus”

The Tortured Poets Department is undeniably an album of heartbreak ballads. There are just so many of them and every one is more sorrowful than the next. “Chloe or Sam or Sophia or Marcus,” however, feels especially tragic thanks to the hesitation and uncertainty in the lyrics. A love filled with promise is over, unceremoniously, but the singer can’t escape wondering if that really is the end or if the “what ifs” will haunt her forever.

Another one of Taylor’s beautifully poignant poems over Aaron Dessner’s classic, ethereal production. A song that infiltrates your bones and tugs at your heartstrings.


4. “I Look in People’s Windows”

Tortured Poets‘ production is purposefully modest, taking a back seat to Taylor’s breathy, heartfelt vocals and impossibly vulnerable lyrics. Whether you prefer Jack Antonoff’s synth-heavy pop trademark or Aaron Dessner’s earthier, transcendent goodness, it’s safe to say both of Taylor’s go-to collaborators understood that this album was not about them, but about Taylor’s words and experiences.

“I Look In People’s Windows” is possibly the album’s simplest song (and shortest, too), as the musician quietly sings over Antonoff’s wistful acoustic guitar, not about grand declarations of love and loss, like the next song on this list, but about something smaller. Taylor uses the metaphor of looking in people’s windows to describe her morbid curiosity about other people’s better, more stable lives, hoping to find the one that got away in one of them.

3. “loml”

It’s difficult to confidently state this about any song on Tortured Poets, but “loml” is maybe the most beautiful poem in the album. This haunting piano ballad is a song about realizing that the person you thought was the love of your life was leading you on. The concept is simple, as is the music, but the lyrics and the way Taylor sings them are so incredibly arresting that “loml” mandatorily wins a place on the podium of Tortured Poets.

Most artists would dream of writing a song like this once in their career, but Taylor Swift wrote a dozen in one album. In the end, there’s no denying what she says in the prologue of her 11th body of work, “it’s the worst men that [she writes] best.”

2. “Who’s Afraid of Little Old Me?”

“Who’s Afraid of Little Old Me?” is “Mad Woman”‘s maddest sister. A bold and angry banger about the long-term effects of a life in the spotlight, particularly the scrutiny that seems to unrelentingly follow Taylor’s career since its early days. The lyrics describe the way the industry and all that it entails have attempted to mold her into one thing, controlling her by breaking her.

Moreso, the song can be universally applied to any situation where you have felt belittled, where your power was undermined and underestimated, which just so happens to be a frequent occurrence in the life of a woman. However you want to interpret “Who’s Afraid of Little Old Me?,” there is an unequivocal strength in Taylor’s rebellion, powered by one of the most interesting instrumentals on the Tortured Poets.

1. “The Prophecy”

More than any of her albums in the past, The Tortured Poets Department functions as a time capsule of a particular moment in Taylor Swift’s life, during which she seems to have experienced extraordinary heartbreak. There is no song more vulnerable than “The Prophecy,” where we find the singer desperate for a sign that tells her that, despite all the disappointing endings of past relationships, there is still hope for a future where she finds lasting love.

“The Prophecy” is a crushing, brutally honest poem with a desperate chorus that acts as a summary of the album. It’s devastating and tortured, but it’s also every bit as beautiful.