June 21, 2023 9:19AM

All 229 of Taylor Swift’s Songs, Ranked

From teen country tracks to synth-pop anthems and rare covers, a comprehensive assessment of her one-of-a-kind songbook through the Midnights era.

By Rob Sheffield

Taylor Swift the celebrity is such a magnet for attention, she can distract from TAYLOR SWIFT THE artist. But Swift was a songwriter before she was a star, and she’ll be a songwriter long after she graduates from that racket. It’s in her music where she’s made her mark on history — as a performer, record-crafter, guitar hero and all-around pop mastermind, with songs that can leave you breathless or with a nasty scar. She was soaring on the level of the all-time greats before she was old enough to rent a car, with the crafty guile of a Carole King and the reckless heart of a Paul Westerberg — and she hasn’t exactly slowed down since then.

So with all due respect to Taylor the myth, the icon, the red-carpet tabloid staple, let’s celebrate the real Taylor — the songwriter she was born to be. Let’s break it down: all 229 tunes, counted from the bottom to the top. The hits, the flops, the deep cuts, the covers, from her raw 2006 debut as a teen country ingenue right up to Midnights

Every fan would compile a different list—that’s the beauty of it. She’s got at least 5 or 6 dozen songs that seem to belong in her Top Ten. But they’re not ranked by popularity, sales or supposed celebrity quotient — just the level of Taylor genius on display, from the perspective of a fan who generally does not give a rat’s nads who the songs are “really” about. All that matters is whether they’re about you and me. (I guarantee you are a more fascinating human than the Twilight guy, though I’m probably not.)

Since Taylor loves nothing more than causing chaos in our lives, she’s re-recording her albums, including the outtakes she left in the vault before. So far, she’s up to Fearless and Red. For the Taylor’s Version remakes, both versions count as the same song. It’s a tribute to her fierce creative energy — in the past couple years she’s released an avalanche of new music, with more on the way. God help us all.

Sister Tay may be the last true rock star on the planet, making brilliant moves (or catastrophic gaffes, because that’s what rock stars do). These are the songs that sum up her wit, her empathy, her flair for emotional excess, her girls-to-the-front bravado, her urge to ransack every corner of pop history, her determination to turn any chorus into a ridiculous spectacle. So let’s step back from the image and pay homage to her one-of-a-kind songbook — because the weirdest and most fascinating thing about Taylor Swift will always be her music.

From Rolling Stone US

A bang-up claim on the Tom Petty classic – she used his original as her live entrance music for a while. Then she switched to Lenny Kravitz’s “American Woman.”Best line: “Oh yeah! All right!”

A teen ditty about a boy who doesn’t realize she’s alive, from pretty much the last moment in history that was possible. Clever pop-obsessive touch: The final steel-guitar twang echoes Elton John’s “Rocket Man.” If you think that’s an accident…this is Planet Tay. There are no accidents.Best line: “We could be a beautiful miracle, unbelievable, instead of just invisible.”

Ironclad rule of pop music: Songs about jumping are never a bad idea. Dig that “listens to Sublime once” vocal.Best line: “I watch you talk, you didn’tnotice.”

Digging deep in the Nineties modern-rock crates, she does right by a previously obscure (to me) nugget from the New Orleans band Better Than Ezra – from 2005!, 10 years after their MTV hit! – as a charity benefit for the Hope for Haiti Now album.Best line: “I’ll never judge you/I can only love you.”

One of the basic rules of stardom is “never punch down” – don’t go after somebody one-thousandth as famous as you – but rules were made to be broken, and Taylor is the girl made to break them. Here, she goes Bruce Lee on a sexual rival who may or may not be the actress who had Alyssa Milano as her babysitter in the erotic thriller Poison Ivy 2. But as usual with Swift, her self-owns are the funniest part of the song.Best line: “She thinks I’m psycho because I like to rhyme her name with things.”

Swift hits the club with her older boyfriend and gets her pheromones scrambled by the sweet young thing across the room. Dig those Eighties synth tones — straight from the first Howard Jones album. Tragic fact: Seven years after she wrote “Enchanted,” Taylor still has zero “find out if dude has a freaking girlfriend” game. The shout-out to her cats Meredith and Olivia is such a cheap ploy, and you know what? It works brilliantly, as cheap ploys usually do when this is the woman working them. This song could rate higher, except she basically did an even better version with “You Need to Calm Down.”Best line: “You should take it as a compliment that I’m talking to everybody here but you.” Listen here.

“I wanna brainwash you into loving me forever / I wanna transport you to somewhere the culture’s clever”—for Tay, that means a fantasy of Gay Paree. But the whole point of this song is that you can make your own Paris wherever you are, just by drawing your own dream map on the bedroom ceiling. And if you have an amour to share the dream with, all the better. “All the outfits were terrible, 2003 unbearable”—sounds like Taylor found somebody’s Friendster photo stash of crop tops and trucker hats. “Did you see the photos? / No, I didn’t, but thanks though” is being kind.Best line: “Privacy sign on the door and on my page and on the whole world / Romance is not dead if you keep it just yours.”

A Big Red Machine ballad sung by Bon Iver’s Justin Vernon, with Taylor in a supporting role. She adds her celestial harmonies, picking up where the Justin/Taylor duets “Exile” and “Evermore” left off. Aaron Dessner summed up the spirit of the project: “Making music with your friends just to make it.”Best line: “So I beg on knees/Can we share IDs?”

“My mind turns your life into folklore” is a clever way to connect Evermore to Folklore, although “Gold Rush” might have sounded more at home on Lover. “Gold Rush” could be a different view of the same torpor as “Happiness” and “Tolerate It,” trying to remember why this relationship once seemed worth the pain.Best line: “My Eagles t-shirt hanging from the door.”

Once upon a time, many Christmases ago, the label made poor Taylor bang out a shoddy quickie holiday album in time for December. She must have wondered, “Why is this happening? Why am I singing ‘Santa Baby’? WTF, shouldn’t I be singing about how in real life I literally grew up on a Christmas tree farm?” It took a few years, but she finally got to jingle all the way, with this impeccably cozy carol.Best line: “Sweet dreams of holly and ribbon / Mistakes are forgiven.”

“You smile that beautiful smile, and all the girls in the front row scream your name.” No relation to the Seventies soft-rock hit by the Carpenters — except they’re both poignant ballads about groupies crushing on distant guitar boys. Well, as Journey warned, lovin’ a music man ain’t always what it’s supposed to be.Best line: “You sing me to sleep every night from the radio.”

Her wintry tribute to Eighties R&B — that sax sounds like it dropped in from a lost Sade album between Promise and Love Deluxe. The highlight of “False God” is the final 30 seconds, where she sings exactly like Drake. She’s showing off, but it’s all right.Best line: “Staring out the window like I’m not your favorite town / I’m New York City.”

Her ballad from Hannah Montana: The Movie, snagging her a cameo in the film. (But the highlight of the soundtrack will always be “Hoedown Throwdown.”) This is where Taylor and Miley crossed light sabers – although they’d meet again. Great title, too – even Taylor might probably admit Miley had her beat in this department, at least until the “Blank Space” video.Best line: “Every sky was your own kind of blue.”

Little-known fact: Did you know Kanye West once went onstage to interrupt Swift’s acceptance speech at the VMAs and threw a misogynist tantrum about how she didn’t deserve an award? Strange but true! “Innocent” was her song publicly forgiving him — over 10 freaking years ago — then they both released brilliant albums and we all moved on with our lives. Dear Lord, if only this story had ended there.Best line: “It’s OK/Life is a tough crowd.”

Baby, let the games begin. Her island-breeze bass blast was a major rebound from her previous hit, one week earlier. (If by “it” she meant “literally any song that’s not ‘Look What You Made Me Do,’” the answer was “extremely ready.”) It stands up to heavy rotation, too, with clever details like the way Ms. I’m Not Much For Dancin’ clears her throat before the first line. The chorus has a little air in the mix, giving the room she needs to pull off her intricate breathy effects; Max Martin really knows how to shape a production around her voice. “He can be my jailor / Burton to this Taylor” – Liz and Dick got married and divorced twice, so those are some hardcore relationship goals.Best line: “I keep him forever like a vendetta.”

One of Taylor’s favorite heroines to write about: the small-town girl who broke free and ran off to the big old city because she wanted to chase the fame, only to wonder if she blew her shot at everyday happiness with the boy next door. (She probably didn’t.) “Midnight Rain” does the Prince trick of a butch/femme duet with her own electronically warped voice, enhancing the mood of nocturnal regret. The road not taken looks real good now.Best line: “My boy was a montage.”

An unsung highlight of the debut – a teen pep talk about self-esteem.Best line: “Seems the only one who doesn’t see your beauty/Is the face in the mirror looking back at you.”

A synth ballad rescued from the Fearless vault, where Taylor bumps into an ex-boyfriend and decides whether she feels like taking the high road or making a scene. Shocker: she makes a scene.Best line: “Hey, I knew I’d run into you somewhere/It’s been a while, I didn’t mean to stare.”

The most “therein” moment on Reputation. Also the only song (after “Look What You Made Me Do”) devoted to the album’s alleged celebrity-complaints concept, though shrewdly playing it for kicks and giggles. “Therein lies the issue” is some quality Swiftian spite content, but it’s that sadistic tongue-clicking “mmm-mmmm” before the second chorus that really brings the Judgement Tay. “Here’s to my mama, had to listen to all this drama” – has your mom met you? She might be used to that by now.Best line: “Feeling so Gatsby for that whole year.”

“Before you, I’d only dated self-indulgent takers” – but here she turns into a self-indulgent taker herself and (surprise!) she likes it, a phone-throwing nightmare dressed like a grocery-shopping daydream. But she’s more in love with more mood swings than she is with the guy.Best line: “You came in wearing a football helmet and said, ‘Okay, let’s talk.’”

The first song Swift wrote with Max Martin and Shellback — the day she met them. It makes sense she left “Message in a Bottle” off Red, since it sounds so similar to “22”— she chose the right one. But it sounds like she’s already stretching ahead to 1989. “How is it in London?” sounds like a fresh take on the transatlantic rendezvous of “Come Back…Be Here.”Best line: “I became hypnotized by freckles and bright eyes, tongue-tied.”

Nothing could be more contrary to the Taylor worldview than the concept of “closure.” Needless to say, she’s opposed to it.Best line: “Don’t treat me like some situation that needs to be handled/I’m fine with my spite and my tears and my beers and my candles.”

She leaves her window open overnight, just in case her ex falls out of a cloud. There’s a great “oooh” in the second chorus — one of those moments you can tell she’s an Oasis fan. (This song makes you suspect “Don’t Look Back In Anger” is a fave.) One of the Fearless-era tunes that gets a drastic glow-up on Taylor’s Version — it sounds infinitely better when she gets to belt it in her adult voice.Best line: “I could stand up and sing you a song/But I don’t wanna have to go that far.”

Tay does the Wham! legacy proud – she should also cover “Wake Me Up Before You Go-Go.” The ache and quaver of her voice fit the George Michael melancholy; this might be the saddest “Last Christmas” since the original. Plenty of us communed with this version on Christmas 2016, the night we said goodbye to the guy who wrote it. R.I.P., George Michael.Best line: “A girl on a cover but you tore her apart.”

Taylor has never once in her life made a long story short, and who would want her to? This synth-pop bop adds a dash of Reputation energy to the stark autumnal vibe of Evermore. I love how if she could go back in time, she’d tell her younger self all the things she actually did say a decade ago. “Your nemeses will defeat themselves before you get the chance to swing” is basically the same sentiment as “people throw rocks at things that shine.”Best line: “If the shoe fits, walk in it till your high heels break.”

From Neil Young to the Beatles, “Tell Me Why” songs are tough to screw up, and even at 19, Tay’s too seasoned to let that happen.Best line: “I need you like a heartbeat/But you know you got a mean streak.”

Inspired by her grandfather, a World War 2 veteran who landed on Guadalcanal in 1942. “Holding hands through plastic” is a stark image of the Covid-19 pandemic.Best line: “Something med school did not cover / Someone’s daughter, someone’s mother.”

A 1989 banger that could have made an excellent single – it sounds a bit like “Out of the Woods,” except with a livelier chorus and a stormier range of electro-Tay sound effects.Best line: “Let me remind you this was what you wanted.”

“Karma is my boyfriend” is a great hook from this surprisingly perky chorus. A Midnights track that feels like a leftover from the past, especially since she already wrote a reply to this one two years ago, with “Long Story Short,” advising “past me” to let go of petty distractions and just let her nemeses defeat themselves.Best line: “Karma is a cat.”

“The moon was high like your friends were the night that we first met” is quite an opening line, and she lives up to it. Especially since those might be the same stupid friends who showed up later at Betty’s party. “Paper Rings” is a girl-group tribute with a pop-punk surge — a song Joey Ramone should have lived long enough to sing. “I wake up in the night and watch you breathe” is a bone tossed to all of us who still fall apart at the bridge of “Last Kiss.”Best line: “I hate accidents, except when we went from friends to this.”

The first outtake she let slip from the Fearless vault was a proof-of-concept coup. Still just 17, she writes a song about getting clean, but decides to keep it a secret, so she can wait six years to release her classic “Clean,” then wait six *more* years to release this prequel. I do not understand how this mind exists — honestly, it’s just scary.Best line: “Your hands in your pockets/And your ‘don’t you wish you had me’ grin.”

Lusty finger-snaps, crushed-out heavy breathing, skipping down 16th Avenue. (Isn’t that underwater in the Hudson River?) “It’s like I’m 17 / Nobody understands” is hilarious considering that when she was 17, she had the world wired to every teardrop on her guitar.Best line: “He’s so obsessed with me, and boy, I understand.”

If you’re a fan of Swift’s Nineties modern-rock radio jones – one of her most fruitful long-running obsessions – check out this shameless tribute to the Cranberries. (But did she have to let it linger? Did she have to? Did she have to?)Best line: “Baby, make me fly.”

“Dancing With Our Hands Tied” has more of Romeo and Juliet‘s actual plot than “Love Story” did. She slips away in secret with a forbidden lover who paints her blue heart gold, over Eighties “Take On Me”-style beats. The saddest line Fiona Apple ever wrote – “I know I’m a mess he don’t wanna clean up” – finally finds a new home in a Swift song: “I’m a mess, but I’m the mess that you wanted.”Best line: “I’d kiss you as the lights went out / Swaying as the room burned down.”

The first time I heard “Welcome to New York,” back in 2014, I thought people would freak out over the explicit pro-queer lyrics. (“Boys and boys and girls and girls” — she was not afraid to burn her bridges.) But of course, people slept on it. So I love how she just did it a little louder for the people in back. Eighties New Wave synth-pop was one of the gayest musical movements ever, but at the time, it was all hidden — virtually none of the genre’s (many) queer artists were out. So it’s fitting how her New Wave homage foregrounds the music’s LGBTQ roots. When she growls, “Damn, it’s 7 a.m.” we all know Taylor has been up pacing the floor at 2 a.m., because that’s what she does.Best line: “Can you just not step on our gowns?”

“Reader, I married him” is one of the most famous lines in 19th century novels, from Charlotte Bronte’s Jane Eyre, so “Dear Reader” is a suitable flex for Quill Pen Taylor, stretching her lit muscles after “The Lakes.” It evokes the end of the “All Too Well” short film, when Author Taylor appears at the bookstore, with a crowd full of readers under her spell. It’s a clever irony for her to warn, “Never take advice from someone who’s falling apart” — especially since the art of falling apart is her favorite topic for giving advice.Best line: “Dear reader, the greatest of your luxuries is your secrets.”

A country collabo with her longtime friends in Haim, for a “Goodbye Earl”-style murder story with a shout-out to Olive Garden. Clever detail: the killer husband reveals his guilt by buying “brand new tires,” continuing Taylor’s recent fascination with shiny wheels. Question: Why did he buy new tires right after committing a murder? Is he the only guy who’s never seen Goodfellas? It’s like Robert De Niro says: “Don’t buy anything!” What a Johnny Roastbeef mistake.Best line: “She was with me, dude.”

I mistakenly thought this Train hit was deep-fried garbage until I heard Swift’s version and realized, “Hey, she’s right – this is the best soy latte I’ve ever had!” Props to Tay for bringing out the hidden greatness in this song – the stargazing lyrics and her voice go together like Mozart and tae bo. (The astrophysicist in my life would like me to point out that you can’t “make it to the Milky Way” because that’s the galaxy we already live in. In fact, you couldn’t leave the Milky Way if you tried. Science!)Best line: “Tell me, did Venus blow your mind?”

Love how this American queen pronounces “Jag-yew-waaar” – has she been listening to Hall & Oates, or has she just reached the English-accent point in her fame arc?Best line: “Up on the roof with a schoolgirl crush / Drinking beer out of plastic cups.”

An easy Red vault track to overlook, but the dance-pop zoom of “The Very First Night” could have fit right on 1989. It makes a worthy part of the trilogy with “Come Back…Be Here” and “Message in a Bottle.” She’s causing trouble up in hotel rooms with a jet-set rock-star boyfriend — a predicament she’d explore in detail more later.Best line: “Don’t forget about the night in L.A./Dance in the kitchen, chase me down the hallway.”

An understated electro-ballad produced with Sounwave, giving thanks for some benevolent fluke of the universe (did some bird flap its wings over in Asia?) that has resulted in a functional romantic situationship. “2,910 days of our love blackout”—that’s six years, or approximately how long Swift has been with Joe Alwyn. And she released it on the 12,000th day of her life? Hardcore. Lifted high by Midnights’ loveliest back-up vocals.Best line: “I was supposed to sweat you out, in search of glorious happenings of happenstance on someone else’s playground.”

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Enchanted to meet you, Goth Taylor. We’ll meet again.Best line: “Something keeps me holding on to nothing.”

Don’t let the title scare you away – it’s a plainspoken and genuinely touching play-by-play recap of a worthwhile date. In fact, “Today Was a Fairytale” and “If This Was a Movie” should trade titles, since this one feels realer and would make a better movie. It could rank higher, except she hugely improved it when she rewrote it as “Begin Again.” (Docked a couple notches for coming from the soundtrack of Valentine’s Day, which is the most dog-vomit flick Jessica Alba has ever made, and I say that as someone who paid money to see The Love Guru.)Best line: “I wore a dress/You wore a dark gray T-shirt.”

Again with the slamming doors. Tay, Tay — even the great songwriters can get away with exactly one slamming door per career. And just to be on the safe side, she throws in pouring rain, photo albums, a little black dress (which rhymes with “mess” and “confess”), a guy throwing pebbles at her window… In other words, this would be the ultimate Swift song — except there are over a hundred better ones. But “The Other Side of the Door” gets a boost from the Taylor’s Version remake — of all the Fearless tunes, this one improves most drastically on the original. Her mature voice tackles the melody in ways her teen voice couldn’t, sprucing up a dud into a keeper. This is the biggest sonic upgrade in the Taylor’s Version project. So far.Best line: “Me and my stupid pride, sitting here alone/Going through the photographs, staring at the phone.”

When Taylor stopped into the BBC’s Live Lounge, she had a surprise up her sleeve: This Eighties pop aficionado busted out a Phil Collins cover, against all odds. “Can’t Stop Loving You” is a 1970s obscurity that Phil turned into a sleeper hit in 2002. As Taylor explained, “I remember driving around Nashville when I first had my driver’s license just screaming the words to this song.” It’s perfect for her — for one thing, it’s about crying in the back of a taxi. If Taylor wants to keep digging into the Phil catalog, maybe she’ll cover “I Don’t Care Anymore.”Best line: “Got your leaving smile.”

In real-life weddings, the preacher hardly ever invites the groom’s ex up to interrupt the ceremony. But if you’re a fan of Tay in stalker mode, this is priceless – crouching behind the curtains in the back of the church, waiting to pounce. “Horrified looks from everyone in the room” – you don’t say.Best line: “It seems I was uninvited by your lovely bride-to-be.”

Taylor sings about a bad situation where she realizes when it’s time to give up and move on — not exactly her specialty. There’s different types of betrayal going on in this song, but the big moment is when she vows, “He’s got my past behind frozen glass, but I’ve got me.” (It’s like Hall & Oates sang: “The strong give up and move on, while the weak give up and stay.” Tay has so much in common with Hall & Oates.)Best line: “Fifteen years, fifteen million tears, begging till my knees bled.”

This Ed Sheeran duet from the Red vault is about two outlaw lovers making an upstate escape in the car — it makes a clever contrast with the drive in “All Too Well (10-Minute Version),” with Taylor at the wheel. This song also has the album’s second-most-memorable cameo from a keychain. Not as dramatic as “Everything Has Changed,” but every bit as intimate. (And if I’m not mistaken, it’s about something good that starts in a getaway car.)Best line: “I could see this view a hundred times/Pale blue sky reflected in your eyes.”

A Nineties R&B trip through the “Lavender Haze,” with two lovers in their own private world, tuning out society and gender roles and social media, blocking out the noise, leaving it all at their door. It’s a kind of love story she’s kept singing about her whole career, from “Ours” to “Holy Ground” to “Call It What You Want.” Taylor rejects “the 1950s shit they want from me,” where “the only kind of girl they see is a one-night or a wife.” Intriguing footnote: At her NYC commencement speech in May, Dr. Swift revealed, “I had a phase where, for the entirety of 2012, I dressed like a 1950s housewife.”Best line: “Staring at the ceiling with you/You don’t ever say too much/And you don’t really read into my melancholia.”

The one Folklore track that sounds like a continuation of Lover, with its languid finger-snapping Motown slink. “Roaring Twenties, tossing pennies in the pool” — Taylor’s long-term relationship with The Great Gatsby just keeps on giving. She closes the book on her twenties, while kissing off this “not exactly roaring at the moment” decade.Best line: “In my defense I have none, for digging up the grave another time.”

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