Ranking the 5 Best Songs on Taylor Swift’s ‘The Tortured Poets Department’

Taylor Swift’s 31-song anthology The Tortured Poets Department is a sprawling multi-album collection combining intimate confessionals with stadium-sized catharsis.

With “tortured poets” as a theme, the list below focuses on words and how Swift uses her personal life’s emotional, sometimes fleeting, moments to create enduring pop songs. The unedited, expanded edition of the album runs for more than two hours, and its sheer expansiveness risks drowning out the essential moments.

At the risk of facing down her fandoms’ wrath, here are the five best songs on Taylor Swift’s new album ranked.  

5. “Who’s Afraid of Little Old Me?”

Track 10 begins with a hazy Lana Del Rey-type verse before exploding into an utter Swiftian chorus. She goes after the music business and returns fire against the “circus life” of her career. Pop stars are commodities, but despite their commercial function, humans still exist behind the celebrity. Swift’s chamber pop anthem derides the most vicious rumors about her and the attempted domestication of a young woman in the music business.

So I leap from the gallows, and I levitate down your street
Crash the party like a record scratch as I scream
“Who’s afraid of little old me?”
I was tame, I was gentle till the circus life made me mean
“Don’t you worry, folks, we took out all her teeth.”
Who’s afraid of little old me?
Well, you should be

4. “The Smallest Man Who Ever Lived”

The song is rumored to be about Matty Healy, who fronts the British pop-rock band The 1975. It’s a scathing attack on an ex and how the romance resulted in a colossal waste of time. Swift is famous for her post-breakup songs, but this one arrives with a special kind of fury that would please Tori Amos. “The Smallest Man Who Ever Lived” is destined for the stadium.

You hung me on your wall
Stabbed me with your push pins
In public, showed me off
Then sank in stoned oblivion
’Cause once your queen had come
You’d treat her like an also-ran
You didn’t measure up
In any measure of a man

3. “Fortnight” featuring Post Malone

The Tortured Poets Department opens with Swift blending confessional fact and Folklorian fiction. “Fortnight” follows Swift after a breakup, and she details her life spiraling into addiction. However, there’s a twist. Swift’s ex moves in next door, and the former lovers must adapt to a new life as friendly neighbors. She begins some kind of healing on “Fortnight.” But she must endure the pain first.

And for a fortnight there, we were forever
Run into you sometimes, ask about the weather
Now you’re in my backyard, turned into good neighbors
Your wife waters flowers, I wanna kill her

2. “But Daddy I Love Him”

Swift uses the metaphor to call out her fan base, and they’ve quickly adopted it as a new favorite. “But Daddy I Love Him” addresses her fans’ backlash against Swift’s brief relationship with Matty Healy from The 1975. It’s a blistering attack on the fanbase she cultivated by letting them into nearly every aspect of her life.

Dutiful daughter, all my plans were laid
Tendrils tucked into a woven braid
Growing up precocious sometimes means not growing up at all
He was chaos, he was revelry
Bedroom eyes like a remedy
Soon enough, the elders had convened
Down at the city hall
“Stay away from her.”
The saboteurs protested too much

1. “So Long, London”

Some listeners consider “So Long, London” a sequel to “London Boy” from her seventh album Lover (2019). The song may be Swift’s goodbye to the old city and her former partner Joe Alwyn. “So Long, London” tops this list not only for the exquisite chorus melody but for Swift’s heartbreaking words. Her take on Britain’s wartime slogan Keep Calm and Carry On is perfect.

I saw in my mind fairy lights through the mist
I kept calm and carried the weight of the rift
Pulled him in tighter each time he was drifting away
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
Thinkin, how much sad did you think I had
Did you think I had in me?
Oh, the tragedy.

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Photo by Matt Winkelmeyer/Getty Images for The Recording Academy