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Swiftature — Top 50 Taylor Swift Songs for Fiction Writers Ranked: 20 -11

Laurel Osterkamp · August 29, 2025

OMG — Taylor has a new album out soon, AND she’s engaged!!

It’s the perfect time to finally resume my series about the top 50 Taylor Swift songs for fiction writers. Honestly, I never meant to take this long, but I’ve been hard at work on a holiday romance I hope to release in a matter of weeks, and that came first. But my WIP is currently being looked at my developmental editors & beta readers, so here we are.

Taylor did me a solid by becoming “hot” again when the timing worked well for me. I’m sure she planned it this way…

Anyway, without further ado, here are my selections for songs 20 thru 11–the best Swift songs for fiction writers!

#20: Tis’ the Damn Season

I parkеd my car right between the Methodist

And thе school that used to be ours

The holidays linger like bad perfume

You can run, but only so far

I escaped it too, remember how you watched me leave

But if it’s okay with you, it’s okay with me

“Tis’ the Damn Season” is at once bittersweet and nostalgic, telling the story of a woman who returns to her hometown over the holidays and reconnects with a lost love. Swift contrasts the aching freedom of escaping your childhood home with the security of staying with your roots. In the song’s refrain, she repeats, “The road not taken looks real good now,” using a literary allusion to Robert Frost’s famous poem. Swift seems to say here that she took the road less travelled by taking risks and rising to stardom. But that didn’t make “all the difference.” In fact, she seems to want to return to the safety of her childhood and this lost relationship. As always, the lyrics here are full of sensory details, similes, and literary tropes, making this feel almost like it could be a Hallmark Christmas movie. It certainly captures the essence of a ninety minute film into a three minute song.

#19: Exile

Second, third, and hundredth chances

Balancing on breaking branches

Those eyes add insults to injury

I think I’ve seen this film before

And I didn’t like the ending

I’m not your problem anymore

So, who am I offending now?

You were my crown

Now I’m in exile, seeing you out

Folklore is chock-full of angsty, melancholy, and emotionally devastating songs, many of which tell the story of lost love. And “Exile” may very well be the most angsty, melancholy and emotionally devastating song of them all. While listening to this duet, we witness an imaginary, post-breakup conversation between two people still mourning their past relationship. Taylor seems to have moved on more than Bon Iver, yet they both revisit their heartache, the destruction of their dreams and their inability to communicate with one another. Throughout the song there are metaphors, comparing their relationship to a film or to popular film tropes. There are also military or geographic metaphors, like “you were my town, now I’m in exile seeing you out,” or “you’re not my homeland anymore, so who am I defending now?” The result is poignant, creating a startling picture of this couple, their dynamic, and the downfall of their love.

#18: Maroon

And I lost you

The one I was dancin’ with

In New York, no shoes

Looked up at the sky and it was maroon

The burgundy on my T-shirt when you splashed your wine into me

And how the blood rushed into my cheeks, so scarlet, it was (maroon)

The mark you saw on my collarbone, the rust that grew between telephones

The lips I used to call home, so scarlet, it was (maroon)

I’ve said it before—Taylor Swift loves color references to express emotions. The most notable example is her title track song, “Red,” which didn’t even make my top 50. (Nothing against the song, it’s great—but there were so many worthy songs to choose from…) Swifties claim that “Maroon” is a more mature version of the song “Red.” I like “Maroon” better for fiction writing because of all the details, and how she combines them to tell yet another story of a relationship. Her lyrics show an intense passion that, in the end, becomes destructive. References to blood, marks on her collarbone, rust between telephones, all paint a picture of a love relationship that becomes unhealthy.

#17: The Black Dog

Six weeks of breathing clean air

I still miss the smoke

Were you making fun of me with some esoteric joke?

Now I want to 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

And I hope it’s shitty

In The Black Dog

When Taylor Swift introduced TTPD during the Eras Tour, she branded it, “Female Rage—The Musical.” She was joking, but not completely. Swift has built an amazing career writing song after song about sad breakups, about being unlucky in love. But “The Black Dog” introduces something else; her rage turns to self-destruction. What a character arc! It’s not her ex’s clothes she wants to burn—it’s her own.  “Now I want to sell my house and set fire to all my clothes,” suggests a detailed and deliberate combination of anguish and fury, one that Swift internalizes rather than acts out on.

#16: Is it Over Now?

Oh, Lord, I think about

Jumping off of very tall somethings

Just to see you come running

And say the one thing I’ve been wanting, but no

Let’s fast forward to three hundred awkward blind dates later

If she’s got blue eyes, I will surmise that you’ll probably date her (no)

You dream of my mouth before it called you a lying traitor

You search in every model’s bed for something greater

The internet says this song is about Swift’s on-again/off-again relationship with Harry Styles. I give “Is it Over Now?” the number sixteen spot for its anthem-like power. It’s catchy and memorable, a reminder of that sometimes less is more when it comes to writing to draw the reader in. Plus, I love the line “lets fast-forward to three hundred takeout coffees later.” Another example of synecdoche! (An AP lit  term meaning when a part represents the whole.)

#15: Look What You Made Me Do

But I got smarter, I got harder in the nick of time (nick of time)

Honey, I rose up from the dead, I do it all the time (I do it all the time)

I got a list of names, and yours is in red, underlined

I check it once, then I check it twice, oh

Ooh, look what you made me do

This song is very straight forward, but if you want lots of Easter eggs and symbolism, just watch the music video. By now, Swift is well known for having “eras” but in 2017, it was still a new concept. “Look What You Made Me Do” is the perfect declaration of a new era, even going so far as saying that “the old Taylor” is dead.  It reminds me of Gloria Gaynor’s “I Will Survive”–she’s been reborn into a smarter, harder version of herself. It’s the type of anthem we all need whenever we’re feeling angry or taken advantage of, expressing those universal emotions with flawless execution.

#14: I Bet You Think About Me

But you know what they say, you can’t help who you fall for

And you and I fell like an early spring snow

But reality crept in, you said we’re too different

You laughed at my dreams, rolled your eyes at my jokes

Mr. Superior Thinkin’

Do you have all the space that you need?

I don’t have to be your shrink to know that you’ll never be happy

And I bet you think about me

They say that comedy is tragedy plus timing. “I Bet You Think About Me” is a funny song about heartbreak, like the first three-fourths of a rom com (but minus the typical happy ending.) I love how she depicts the guy here, with his “organic shoes” and his “million dollar couch,” who says Swift must be insane because she wrote a song about him…it’s very meta. While she doesn’t use a ton of figurative language (though, I love “you and I fell like an early spring snow,) the details she provides are both snarky and striking. That’s why, for its ability to convey both character and voice, I give “I Bet You Think About Me”–a song from Red’s vault—the number fourteen spot. 

*side note: I love this song so much that I used its title for my small-town, Austen-inspired, contemporary rom-com novella. AND YOU CAN READ IT FOR FREE! Here you go: Read I Bet You Think About Me

#13: Hits Different

I used to switch out these Kens, I’d just ghost

Rip the Band-Aid off and skip town like an asshole outlaw

Freedom felt like summer then on the coast

Now the sun burns my heart and the sand hurts my feelings

And I never don’t cry (no, I never don’t cry) at the bar

Yeah, my sadness is contagious (my sadness is contagious)

I slur your name ’til someone puts me in a car

I stopped receiving invitations

I may have picked this song as number 13—Swift’s favorite number—solely because of the line, “Now the sun burns my heart and the sand hurts my feelings.” I also love how self-aware it is. This song is a portrait of a woman who’s unapologetic about falling apart over a guy who she knows isn’t worth her time. There’s something very refreshing about the attitude of not giving a fuck. 

#12: Snow on the Beach

One night, a few moons ago

I saw flecks of what could’ve been lights

But it might just have been you

Passing by unbeknownst to me

Life is emotionally abusive

And time can’t stop me quite like you did

And my flight was awful, thanks for asking

I’m unglued, thanks to you

And it’s like snow at the beach

Weird but fuckin’ beautiful

Flying in a dream, stars by the pocketful

You wanting me tonight feels impossible

But it’s comin’ down, no sound, it’s all around

The entire song is a simile! It’s dreamy and ethereal, about a perfect moment when fate and love converge.

In Swift’s own words: “The song is about falling in love with someone at the same time as they’re falling in love with you…And you’re kind of looking around going, ‘Wait, is this real? Is this a dream?… Kind of like it would be if you were to see snow falling on a beach.”

“Snow on the Beach” inspired me while I was writing my novel, The Side Project. It’s a contemporary romance that takes place in Bemidji, MN, a northern town with a huge, beautiful lake. Snow on the beach is a common occurrence in Bemidji, and the song perfectly describes the type of love I was trying to capture.

#11: The Smallest Man Who Ever Lived

I would’ve died for your sins
Instead, I just died inside
And you deserve prison, but you won’t get time
You’ll slide into inboxes and slip through the bars
You crashed my party and your rental car
You said normal girls were boring
But you were gone by the morning
You kicked out the stage lights but you’re still performing
And in plain sight, you hid
But you are what you did

And I’ll forget you, but I will never forgive
The smallest man who ever lived

The slow, careful build in “The Smallest Man Who Ever Lived” is masterful. It begins with quiet, probing questions and subtle accusations. But once Swift reaches the bridge, the devastation is sudden and inescapable. I love this song for fiction writers because the groundwork is laid out in the beginning, building to climax that we’re unaware of. But once we arrive, it’s both shocking and inevitable. Also, Swift uses paradox, irony, hyperbole and zeugma (using the same verb in two different ways) with effortless skill. 

 

Okay! Now we only have the top ten left. I’m going to make any promises about when I’ll post them, except that it will be before early October. Because, who knows how my selections might change after Life of a Showgirl releases?

In the meantime, if you haven’t already:

Read Top 50 Taylor Swift Songs for Fiction Writers, #s 50-41

Read Top 50 Taylor Swift Songs for Fiction Writers, #s 40-31

Read Top Taylor Swift Songs for Fiction Writers, #s 30-21

Also, make sure to read “Love and Poetry,”  my short story written while reading Taylor Swift. It’s free to download, and you don’t even have to subscribe to my newsletter! (But if you’d like to subscribe, I’d love to have you. Click here!)

Read “Love and Poetry”

(a short story written while listening to Taylor Swift)

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