Taylor Swift doesn’t sleep much. Yes, it’s safe to assume it takes some long days to become the songbird of a generation, but her nocturnal tendencies had been spelled out long before she decided to write a concept album about sleepless nights throughout her life. Only the pouring rain rivals the wee hours as the ideal setting for a Taylor Swift song. Her catalog of tracks about staying up late is about to double, as it turns out she’s penned exactly 13—could it be any other number?—songs that reference midnight or the middle of the night. So, before we have another Taylor’s Dozen to contend with, let’s rank them. The following is a definitive and completely correct list of all of Swift’s songs that take place, at least in part, in the middle of the night. Note: only songs referencing “midnight” or the “middle of the night” were considered, though 3 a.m., 2 a.m., 2:30 a.m., and 1:58 have all offered more than their fair share of lingering questions to keep her up. Seriously, she might be a vampire. OK, to the list!
1. “All Too Well”
’Cause there we are again in the middle of the night
We’re dancing ‘round the kitchen in the refrigerator light
This might be all too obvious, but the most legendary song in Swift’s catalog could be nowhere else but in the no. 1 spot. Take your pick between the original version or the 10-minute version, but “All Too Well” is Swift at the peak of her powers in crafting vivid scenes into gut-wrenching songs. The triumph of the 10-minute version is that it equaled the original in lines that transport a listener to the very moment of Swift’s heartbreak—the car keys, the bathroom, the birthday party. But the OG version of “All Too Well” has all you need to know, and Swift doesn’t need a short film or anything more than a few words to put you right smack-dab in the kitchen of a Brooklyn brownstone feeling the high before the fall.
2. “Better Man”
Sometimes, in the middle of the night, I can feel you again
But I just miss you, and I just wish you were a better man
It was quite the flex for Swift to give one of her very best songs away, which she did with “Better Man” to Little Big Town in 2017 before releasing her own version as a vault track on Red (Taylor’s Version) in 2021. There’s another late-night vignette that comes through as clear as day in this song:
I wish it wasn’t 4 a.m., standing in the mirror
Saying to myself, you know you had to do it
But the best of “Better Man” comes from its directness, the quiet strength it gets from telling you instead of showing you exactly how she feels. The teenage girl who snarled that “it rains in your bedroom, everything is wrong,” grew up, and now it sounds like “we might still be in love if you were a better man.” Chills.
3. “You Belong With Me”
Oh, I remember you driving to my house
In the middle of the night
By the time Swift released this hit from Fearless, she was already a regular at singing about late nights. Come to think of it, she danced “all night long” in her very first single, “Tim McGraw.” But it is true that, if we consider only references to the middle of the night, “You Belong With Me” contains her first, which is sort of like saying it’s the sonic equivalent of early Homo sapiens discovering fire. The top two tracks here thrive based on the superpower we most often associate with Swift—her lyrical writing—but “You Belong With Me” showcases her other best tool, her knack for melodies. You can’t not scream-sing this one.
It feels like a perfect night
For breakfast at midnight
You could convince me pretty easily to flip this song and the next one in these rankings, but “22” is somehow underrated–it peaked at no. 20 on the Billboard Hot 100–in a way that makes less than zero sense to me. This was the song that first brought us “not a lot going on at the moment,” and the canonical recovery from that 21st birthday party. Swift’s “Squad” era was, err, complicated, but “22” is the best it brought us, one of the rare songs in her discography that’s not about a one-on-one relationship but the joy of being with a beloved group (the two other songs that fit this mold are, to me, “New Romantics,” and “Long Live,” which makes me wonder if she should do this more). It seems like “22” gets treated either as the little sister to “We Are Never Ever Getting Back Together” and “I Knew You Were Trouble,” the other poppy hits off Red, or like a warmup for “Shake It Off,” but it should stand on its own. Happy, free, confused and lonely at the same time, and one of her most fun songs ever.
You come and pick me up, no headlights
The fact that this song comes in fifth here is good news for the theme of the Midnights album, because it takes some heavy hitters in the category to push one of the best-sounding songs in Swift’s entire catalog down the list, though I could certainly hear arguments it deserves at least the no. 4 slot. The soundtrack to the 1989 tour’s famous (infamous?) catwalk moments, is there another song in the history of music we can say with certainty has made Serena Williams, Julia Roberts, Matt LeBlanc and Russell Wilson all dance? “Style” was proof of concept for the retro-ish synth-pop of 1989, all groove and vibes and attitude. I wonder who it’s about?!
6. “Last Great American Dynasty”
They say she was seen on occasion
Pacing the rocks, staring out at the midnight sea
“There goes the loudest woman this town has ever seen”—this song is a master class in self-mythologizing while, technically, writing about someone else. Swift’s biography of Rebekah Harkness, the widowed socialite who was the talk of Westerly, Rhode Island, where she lived in an oceanside mansion called “Holiday House,” contains a twist at the end in which Swift reveals herself to be the home’s current occupant and owner, positioning herself as a modern-day Harkness—scandals included. It’s a feat in and of itself to make a song about one’s massive beach house this cheeky and charming, though perhaps we’ve all just been lulled into submission by Aaron Dessner’s dreamy slide guitar. In true Rhode Island fashion, the best part comes at the bridge, where the lines leading up to the narrative twist, which include the midnight reference, are set against chords that toggle from major to minor and back again, building up to the big reveal.
7. “Nothing New” ft. Phoebe Bridgers
And I wake up in the middle of the night
It’s like I can feel time moving
The Sad Girl Pop national anthem carries the distinction of being the first Swift song in which a female featured artist gets a whole verse, with Bridgers doing the honors. Their voices mix beautifully, and the harmonies and traded lines between a pop star of the moment and another four years her elder on a song about the anxiety of carrying on a career when you’re not the next big thing anymore just makes me want to give both of them a big hug.
8. “...Ready for It?”
In the middle of the night, in my dreams
You should see the things we do, baby (mmm)
The throat-clearing cough at the beginning of this song was the perfect way to reset for the opening track on Reputation—Swift made sure she had everyone’s attention. There’s an embarrassment of richness in textures on this song, from the throat-clear in the intro to the breezy tropical-house synths on the chorus to the dubstep drops and programmed drums peppered through the verses to the way Swift repeats words like “I-I-I see,” that somehow get woven together.
9. “New Year’s Day”
I want your midnights
But I’ll be cleaning up bottles with you on New Year’s Day
While this is a beautiful song that closes Reputation on a contented note, and it serves as more evidence that songs mentioning midnight is a strong category for Swift, I ding “New Year’s Day” a little because it doesn’t give much musically in the verses. But by the time the song finishes with Swift singing two iconic lines—“please don’t ever become a stranger whose laugh I could recognize anywhere” and “hold on to the memories, they will hold on to you”—in a round with herself, I am a puddle on the floor alongside the glitter.
Not the things that haunt me in the middle of the night
Another album closer, this one off of Lover takes a bit of patience to get to the payoff. That reward comes before the spoken word coda on a bridge where Swift begins to sing with the echo of her own voice lyrics that echo her old songs: “I once believed love would be burning red, but it’s golden, like daylight.” (In 2019, Swift told Ryan Seacrest that she almost named the album Daylight, but felt it was too on-the-nose as a follow-up to Reputation’s darkness.)
In the middle of the night
When I’m in this dream
It’s like a million little stars
Spelling out your name
A Luna Halo cover off of Fearless, it’s probably unfair for a song Swift didn’t write herself to have to stand up on this list, but it serves as proof that this song was well selected for her because it contains one of her favorite references. I just love the way she sings “come on, come on” in this one.
There is a glorious sunrise
Dappled with the flickers of light
From the dress I wore at midnight, leave it all behind
This song contains some stunning imagery, and she gets some technical points for how well the lyrics fit with Dessner’s composition, but this is the rare Swift song in which I just can’t get into the melody.
13. “You Are in Love”
Small talk, he drives
Coffee at midnight
It’s better live, and truth be told, I’d rather listen to this song than “Happiness,” though I think the latter deserves the spot ahead on this list because of some degree-of-difficulty points. But I’d also take the build of “This Love,” the storytelling on “Clean,” or the energy of “All You Had to Do Was Stay,” “I Wish You Would,” or “How You Get the Girl,” over this track if we’re talking 1989 deep(-ish) cuts.