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

An ode to making up after a fight that was all your fault: “Tell me that I’m all you want / Even when I break your heart.” In a good old-fashioned Taylor metaphor party, she compares herself to an arsonist, a wrestler, an island, a prison warden and an ambulance siren.Best line: “Fighting with a true love is boxing with no gloves.”

One of her most pop-friendly early hits, singing in the role of a high school geek crushing on her best guy friend. When he comes out in college, they’ll have a few laughs about this. And never let us forget the wisdom of Alicia Silverstone in Clueless: “Searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie.”Best line: “She wears high heels, I wear sneakers/She’s cheer captain, and I’m on the bleachers.”

She falls under the hypnotic spell of a magician, who gets her heart trip-trip-tripping and skip-skip-skipping. For a magic trick of her own, she stops the music cold to whisper “one-two-three.” A great moment that lets you know Swift — like the rest of us — has been listening to Lorde.Best line: “I’m so chill but you make me jealous.”

A dramatic piano-and-strings ballad from Fearless, showing off how much her voice has deepened between her first two albums.Best line: “It’s taken me this long, baby, but I figured you out.”

Her kickiest left-field cover, from Speak Now Live. “I’d love to play you some music that I’m a fan of that’s come from L.A. – is that OK?” she asks the West Coast crowd, strumming her guitar. “This one came out in 1981 – eight years before I was born!” Virtually nobody seems to recognize it or sing along. Kim Carnes hit Number One with “Bette Davis Eyes,” but it was written by the great Jackie DeShannon, the only songwriter to collaborate with both Randy Newman and Jimmy Page. (Page wrote “Tangerine” for DeShannon!) The fact that Swift loves this classic ode to romantic espionage explains a lot.Best line: “She’s pure as New York snow/She’s got Bette Davis eyes.”

She’s so lucky, she’s a star. For the record, T.S. did cover “Lucky” live once (and damn well, too), as a Britney tribute in Louisiana back in 2011. This song got the ultimate real-life twist years later: the Red (Taylor’s Version) remake came out the same day Britney finally got free.Best line: “Everybody loves pretty, everybody loves cool/So overnight you look like a Sixties queen.”

A very Taylor dilemma: “Does it feel like everything’s just like second-best after that meteor strike?” She gives a hint about this meteor by opening the song with a sample from “Out of the Woods.” Taylor cross-examines an ex with a slew of questions, although she wishes she didn’t already know the answers. There’s a great flashback to “Betty” in the chorus, when two lovers kiss in a crowded room, in front of all their stupid friends.Best line: “It was one drink after another/Fucking politics and gender roles.”

A clever transitional single – great verses, grating chorus, pithy lyrics with a shout-out to her obvious inspiration, Robyn’s “Dancing on My Own.” As a lead single, “Shake It Off” might have seemed meager after 1989 came out – she was holding back “Blank Space” and “Style” and (Lord have mercy) “New Romantics” for this? But “Shake It Off” got the job done, serving as a trailer to announce her daring Eighties synth-pop makeover.Best line: “It’s like I got this music in my mind, saying it’s gonna be all right.”

She and Ed Sheeran wrote this duet together in her backyard while bouncing on a trampoline, because of course they did. Why is Ed such a great duet partner? Because you can hear that he’s really listening to her.Best line: “All I’ve seen since 18 hours ago is green eyes and freckles and your smile.”

The most stripped-down confession on Folklore, just her solo voice and a few guarded hopes for the future. She tries to scale her dreams down to a graspable size, asking, “Would it be enough if I could never give you peace?”Best line: “Our coming-of-age has come and gone.

The saddest break-up song ever inspired by a movie where Gina Rodriguez plays a Rolling Stone music critic, in Jenn Kaytin Robinson’s Oscar-worthy Netflix comedy, Someone Great. It really soars in the live acoustic version from her Paris concert special, especially the hyperventilating bridge. Good question: “If the story’s over, why am I still writing pages?” Taylor, have you met yourself?Best line: “I asked the traffic lights if it’ll be all right / They say ‘I don’t know.’”

Finally, her long-overdue metal move, from The Hunger Games: Songs from District 12 and Beyond.Best line: “Every lesson forms a new scar.”

“Oh my, what a marvelous tune” sounds like a quaint chorus, yet she makes it stick, in an F. Scott Fitzgerald-themed whirlwind romance. This Red deep cut just sat there waiting for its moment to shine, until it blew up into her de facto sequel “The Last Great American Dynasty,” with a nastier perspective on the same ritzy social scene. Nobody knows how to play the long game like Taylor.Best line: “We snuck into a yacht-club party / Pretending to be a duchess and a prince.”

She tries on the moody “bad girl goes to church” vibe of Madonna circa Like a Prayer – addicted to love, falling from grace, going down on her knees to beg for one more kiss.Best line: “My name is whatever you decide.”

She added this to Fearless at the last minute – just what the album needed. It’s a blast of high-energy JoBro-baiting aggro on her most anomalously shade-free album. “It rains in your bedroom” is a very on-brand Tay predicament.Best line: “Did I say something way too honest? Made you run and hide like a scared little boy?”

One of the top-notch Fearless (Taylor’s Version) vault tracks. Like so many of her songs from this era, it has a giant Oasis-style hook: “You took me home, but you just couldn’t keep me.” Plus a bonus one in the bridge when she sings, “I’m so scaaared of how this ends!” What does it mean that the best Oasis songs of the past 20 years are Taylor songs?Best line: “You’re all I want, but it’s not enough.”

A touching duet with the Dixie Chicks (their final song under their old name) for her countriest tune in years, about her mother’s battle with cancer. It’s definitely heavy to hear the teenager who sang “The Best Day” and “Never Grow Up,” once so mortified her mom was dropping her off at the movies, now an adult driving her mom to the hospital.Best line: “Holy orange bottles / Each night I pray to you.”

A highlight of the Midnights 3 A.M. Edition. “High Infidelity” goes deep into the perils of musicians dating musicians, from “Put on your records and regret me” to “Put on your headphones and burn my city.” Taylor uses audio distortion as a metaphor for a bad romantic connection, a la Elvis Costello’s “High Fidelity,” though Midnights collaborator Zoë Kravitz also starred in the reboot of the classic High Fidelity. As for the question of what she was doing on April 29, 2016…listening to Lemonade and crying over Prince, like the rest of us?Best line: “There’s many different ways that you can kill the one you love/The slowest way is never loving them enough.”

One of the rare ballads where she goes crawling back to an ex she treated like dirt – and she’s surprisingly effective in the role. Although breaking into the guy’s house is a little extreme. (If she’s blocked by the chain on his door, that means she already picked the lock, right?) And sorry, but you’re seriously dreaming if you think I’m bothering to Google the name of that Twilight guy, don’t @ me.Best line: “It turns out freedom ain’t nothing but missing you.”

Can you even imagine the songwriter who wrote “White Horse” in her teens was already planning to write “Tolerate It” in her 30s? She might have taken inspiration from Rebecca, but it feels more like a Carole King song from the 1970s — trapped in a dead-end marriage where something inside just died. Taylor called this part of Evermore “the ‘unhappily ever after’ trilogy of marriages gone bad.”Best line: “Now I’m begging for footnotes in the story of your life.”

We’re already at the zone on this list where every song seems like it should be ranked even higher, except it’s just so crowded at the top. For almost any other artist, “I Almost Do” would have been a career peak. A Red slow jam that could have worked even better sped up into a punked-out rocker — though it’s plenty affecting as is.Best line: “Every time I don’t, I almost do.”

People sure do love to complain about this song – in fact, the most authentically New York thing about it is how it sends people into spasms of mouth-foaming outrage. An explicitly queer-positive disco ode to arrivistes stepping out in the city that invented disco – “You can want who you want, boys and boys and girls and girls” – that will be bugging the crap out of you in rom-coms for years to come. (It made me throw a napkin at my in-flight screen during How to Be Single, when Dakota Johnson’s cab is going the wrong way on the Brooklyn Bridge – and I love this song.) Bumped up a few bonus notches for pissing everyone off, since that’s one of this girl’s superpowers.Best line: “Searching for a sound we haven’t heard before/And it said welcome to New York.”

Why did it take her five albums to get to Alice in Wonderland? Needless to say, Taylor Alison Swift fits right in on the other side of the looking glass, with white rabbits and Cheshire cats. Feed your head!Best line: “It’s all fun and games till someone loses their mind.”

This Fearless outtake would have made quite a highlight on the album. How did she let this one get away? Was it just too damn sad, even by *her* standards? To think of all the years we missed out on being traumatized by “You threw your arms around my neck/Back when I deserved it.” “We Were Happy” has both Liz Rose *and* Aaron Dessner in the credits, making this the perfect storm of Taylor weepers.Best line: “Oh, I hate those voices telling me I’m not in love any more.”

“They say ‘move on,’ but you know I won’t” — yes, we know. She’s always had a knack for songs about unrepentant old ladies, ever since her teens, and this “Mad Woman” could be Betty or Inez a few years down the line. But she could also be the heroine of “Dear John” or “15,” all grown up.Best line: “Women like hunting witches too / Doing your dirtiest work for you / It’s obvious that wanting me dead has really brought you two together.

Nice one, London! You have inspired a Taylor Travelogue even more over-the-top than “Welcome to New York,” with visits to Camden Market, SoHo, Highgate, and everyone’s favorite tourist destination, Hackney. As the English are so fond of saying, she over-eggs the pudding, and no wonder some skeptics got their knickers in a twist, but her Britpop tribute evokes the louche music-hall parodies of London bands from Madness to Blur. (She’s clearly been bumping Side One of Parklife.) The best part of this song is its wide-eyed enthusiasm, the least London of emotions. We need more of these, please — maybe she’ll do “Paris, Je T’Aime” or “Arigato Kyoto.”Best line: “Stick with me, I’m your queen / Like a Tennessee Stella McCartney on the Heath.

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A somber piano ballad about getting stood up on your 21st birthday. This song got a major boost from the sequel “Happiness,” which Taylor happened to release exactly ten years after the party — just in time for her 31st birthday. But it stands out even more on Red (Taylor’s Version), as a companion piece to the expanded “All Too Well.” Has there ever been a more momentous birthday party in music history?Best line: “There in the bathroom/I try not to fall apart.”

Could this be a hidden sequel to the Romantic poetry fetish of “The Lakes”? Dorothy was Wordsworth’s sister, muse and closest companion, just as Augusta was Lord Byron’s sister. “Dorothea” is the flip side to “’Tis the Damn Season,” sending a long-distance dedication to an old flame who moved on to a shinier life in Hollywood.Best line: “The stars in your eyes shined brighter in Tupelo.”

Another through-the-years romance, featuring a snowglobe. This 1989 outtake was underrated for years, until she cleverly interpolated it into the “Lover” video — where it all takes place inside the snowglobe.Best line: “For once you let go of your fears and your ghosts.”

Romeo meets Juliet: Proof that star-crossed teen romances never go out of style. But changing the plot of Romeo and Juliet so these two crazy kids end up together — now that’s some endearing Taylor hubris. She keeps going back to the well of Shakespearean tragedy, quoting Julius Caesar in the “Look What You Made Me Do” video. It’s never been clear what the line, “I was a scarlet letter,” is doing in this song, but now it’s a hint that Tay was just a few years away from going Full Hester Prynne in “New Romantics.”Best line: “Just say yes.”

Back when Taylor broke up with that hipster dude in 2012, the one who was into “some indie record that’s much cooler than mine,” he was probably listening to Bon Iver. (“Beth/Rest,” damn.) She and Justin Vernon blend their very different voices, for the story of a Romeo and Juliet who never learned how to read each other’s minds. At first it sounded like their vocals just don’t fit together — yet that’s what the song is about. It really soars in the final minutes, as the piano and strings build.Best line: “Like you’d get your knuckles bloody for me / Second, third, and hundredth chances / Balancing on breaking branches / Those eyes add insult to injury.”

When she finally gets around to 1989 (Taylor’s Version), this song stands to gain most. Jack Antonoff was just learning how to record her voice, and wow, he wasn’t even halfway there yet — it’s the production equivalent of a snowmobile wreck. Why did this song need male Tarzan yodels? It deserves a do-over, since the lyrics are packed with poignant details — did they take the Polaroid couch selfie before or after they moved the furniture so they could dance? The best version is live at the Grammy Museum in 2015 — no yodels, just Taylor emoting at her piano.Best line: “Two paper airplanes flying, flying, flying.”

She wrote this Lana-esque tale as a political allegory — looking at the whole country as one big high school where the damsels are depressed, and the mean cheerleaders leer at bad, bad girls.Best line: “The whole school is rolling fake dice / You play stupid games, you win stupid prizes.”

She goes all Kate Bush, pursued across the moors by the hounds of love. This 1989 deep cut is underrated, but count on “I Know Places” to loom large in her canon over the years.Best line: “My love, they are the hunters, we are the foxes.”

A desolate break-up lament, lifted by Aaron Dessner’s melancholy piano. Every Taylor album needs a tragic New York City romance, and “Hoax” revisits the holy ground where she’s loved and lost before — even on her least metropolitan album. “You know you won so what’s the point of keeping score?” is an apt question from such a compulsive emotional score-keeper.Best line: “Don’t want no other shade of blue but you.”

The dawn of Petty AF Tay, as she serves her ex beatdown threats. Every boy who ever complained when Taylor wrote about him – this is where you officially got fair warning.Best line: “Watch me strike a match on all my wasted time.”

A Southern Gothic folk ballad in the Folklore/Evermore mode, from the movie Where the Crawdads Sing. It’s the story of a girl on her own in the North Carolina marshland, guarding secrets she’ll never share with anyone but the night. In many ways, “Carolina” feels like a sequel to “Cruel Summer,” but with bloodier secrets and a darker night.Best line: “Carolina pines, won’t you cover me? / Hide me like robes down the back road.”

Her tribute to Mama Swift. A weapons-grade tearjerker and not to be trifled with in a public place. NSFW, unless you are a professional crier.Best line: “You were on my side/Even when I was wrong.”

You could credit this song with single-handedly driving John Mayer out of the pop heartthrob business and into the Grateful Dead – which is just one of the things to love about it. Along with the Joey Ramone-style way she says, “Next chapter!”Best line: “See me nervously pulling at my clothes and trying to look busy.”

“Cold was the steel of my axe to grind for the boys who broke my heart / Now I send their babies presents” — let the record show that Taylor dropped this line into the world two days after Joe Jonas became a dad. It’s official: she plans literally everything. “Invisible String” revisits some of the places she’s traveled, with a color and a memory for each one, over acoustic finger-picking.Best line: “Green was the color of the grass where I used to read at Centennial Park.”

A seminar on girl hearts and the wooing thereof, with Coach Taylor offering a pep talk to girl-curious boys everywhere. She busts out her trusty acoustic guitar, teardrop stains and all, just to turn it into a beatbox.Best line: “Stand there like a ghost shaking from the rain / She’ll open up the door and say ‘Are you insane?’”

Good question, Taylor: “Is it insensitive for me to say, ‘Get your shit together so I can love you?’” She joins her kindred spirits Aaron Dessner and Justin Vernon in their band Big Red Machine, in this highlight from their album How Long Do You Think It’s Gonna Last? “Renegade” is a love story where she’s trying to brighten the world of somebody who’s in love with the darkness. It could be her answer song to the Eagles’ “Desperado,” except with a bit more in the human compassion department.Best Line: “Is it really your anxiety that stops you from giving me everything? Or do you just not want to?”

Loaded with classic girl-group flourishes, right from the opening “Be My Baby” drum beat. Plus, it begins and ends with her finest humming solos. If she wanted to hum on every song, she could make that work.Best line: “All those other girls, well, they’re beautiful/But would they write a song for you?”

Taylor wrote “Babe” with Train’s Patrick Monahan, but tossed it to the babes of Sugarland. She sang lethal back-up vocals on their 2018 hit version — not to mention playing the femme-fatale supervillain in the Mad Men-style video. But it was worth the wait to get her own version on Red (Taylor’s Version), with Tay lingering over the “promises, promises” hook.Best line: “This is the last time I’ll ever call you ‘babe.’”

Taylor should begin more songs with the line “I have this thing where…”, right? She has LOTS of this thing. “Anti-Hero” addresses her public persona, in the tradition of Taylor Lead Singles, as opposed to her private or creative life, with self-deprecating quips in every verse, and the sing-along chorus: “It’s me! Hi! I’m the problem, it’s me!”Best line: “Sometimes I feel like everybody is a sexy baby/And I’m the monster on the hill.”

A pissed-off highlight of the debut, with an Oasis-worthy chorus. Savor the perfect Liam Gallagher way she milks the vowels of “begging for forgiveness at my fee-ee-eet.”Best line: “It was a moment of weakness, and you said yes.”

A love triangle that gets lowdown and vicious: “I don’t dress for women / I don’t dress for men / Lately I’ve been dressing for revenge.” The hint of this sexual vigilante seducing her lover’s wife adds a bit of spice, as does the idea of using cosmetics as a fatally glam murder weapon.Best line: “Draw the cat eye sharp enough to kill a man / You did some bad things but I’m the worst of them.”

Teen Romantic Tay meets Bitter Adult Tay in a superbly disenchanted breakup ballad that gives up on princesses and fairy tales.Best line: “I’m not the one you’ll sweep off her feet/Lead up the stairwell.”

A cheating ballad that can turn me into a godforsaken mess any time. The guitar has a wistful “Last Kiss” tinge, except instead of sneaking peeks at an ex’s social-media photos, it’s all sordid meetings in the parking lot, where all getaway cars end up. The muted regret boils over in the bridge, as she snarls: “Don’t call me kid, don’t call me baby.” The definitive version is from The Long Pond Studio Sessions, with Aaron Dessner stretching out on guitar.Best line: “Take the words for what they are/A dwindling, mercurial high/A drug that only worked the first few hundred times.”

The opening act of Mr. Casually Cruel, a guy Taylor has kept meeting in her songs ever since. How did she possibly leave a song this strong off Fearless? Because she clearly figured that she needed to save “casually cruel” for an even better song a few years down the road. (One Mr. Casually Cruel wears “a well-pressed suit,” the other wears plaid shirts.) Poor Joe Jonas—now all her exes know that Taylor sends their babies presents, it means there’s a song on the way. “Mr. Perfectly Fine” was the song that truly proved her Taylor’s Version project was for real—the outtakes from her vault weren’t leftovers or juvenalia, but bona fide Swift songs. Never be so casual you forget to be cruel; never be so cruel you forget to be casual.Best line: “Sashay away to your seat/It’s the best seat in the best room.”

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