October 7, 2025 6:04AM

All 286 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.

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 286 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 and The Life of a Showgirl.

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. (Reputation and her debut are the only ones she hasn’t released 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

“I would stay forever if you say ‘Don’t go’ / But you won’t.” A 1989 vault outtake co-written with Eighties hitmaker Diane Warren, “Say Don’t Go” is relatively straight-forward and smooth compared to its peers, with echoes of “Mirrorball” in the tightrope imagery.Best line: “We’re a shot in the darkest dark.”

A light-hearted ode to childhood innocence, with swingsets and dragonflies.Best line: “Long may you roar at your dinosaurs.”

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.”

If you were a Taylor fan in 2010, you probably remember some of the mind-blowingly stupid cliches that experts kept saying about her. “Castles Crumbling” shows that she wondered if these experts had a point. (They didn’t.) It’s wild that she wrote this troubled-ingenue lament three years before “Nothing New.” But Taylor was already feeling that Monster On The Hill terror when she was 20. In “Castles Crumbling,” she bonds with Paramore’s Hayley Williams—two peers who grew up in public at the same time, two women who learned early that people throw rocks at things that shine. It makes sense since Taylor loves Paramore almost as much as she loves castle imagery.Best line: “You don’t wanna know me / I will just let you down.”

Welcome to the dawn of the Taylor sports-metaphor era. “When I touch down / Call the amateurs and cut them from the team”? “The Alchemy” feels like her post-Super Bowl “Dropkick Me Travis Through The Goalposts of Life” statement, and this is just the beginning. Best line: “These blokes warm the benches.”

Subtitle: “So I Sang About You First Thing On My Album.” So yeah, maybe that’s the opposite of forgetting — it’s technically known as “reminding.” Letting go of the past, moving on, calming down — let’s face it, those aren’t exactly topics where you look to Taylor for guidance. That’s why we love her — she never lets go. (She hasn’t forgotten Drew!) But there’s something quintessentially Tay about how she keeps nudging to impress you with how indifferent she is. Her Aubrey Graham shout-out is fitting, since these two are the champion overfeelers of our time.Best line: “In my feelings more than Drake.”

The trad country sound she soon left behind, from her Beautiful Eyes EP.Best line: “Wake up, and smell the breakup/Fix my heart, put on my makeup.”

You see, kids, when your English teacher and your gym teacher love each other very much, songs like this happen, so be careful. Sabrina Carpenter had us all thinking she’d cornered the market on genitalia-positive tunes rhyming “eyes” and “thighs,” but showgirls love a challenge, along with a kicky Chic-on-Motown guitar groove. If “Wood” is more erectile tissue than you can bear to allow inside your ear, that’s totally understandable — it sounds like her showgirl role model is Lily Von Shtupp. But I love how the chorus includes the sound of Miss Thing literally knocking on wood—that’s how you know this comes from the same masterminds who slipped that ballpoint-pen click into the chorus of “Blank Space.” Best line: “Daisy’s bare naked, I was distraught.”

Taylor officially joins the family as the fourth Haim sister. This anger-and-lust guitar jam was a highlight of their excellent Women In Music, but it gets even better with Sister Swift singing along. It’s funny they didn’t have her do the line “Watching the sun rise from the kitchen counter,” since she’s the one who’s on a mission to have emotional experiences in every square inch of the kitchen.Best line: “You needed ass/Well, what’s wrong with that?”

A gorgeous duet full of low-key nuances – her humming after the first verse, that “sorry, sorry, sorry” fade, the way Colbie’s voice lifts hers.Best line: “It’s tragedy, and it’ll only bring you down.”

A rare case where she retools somebody else’s song on one of her proper albums – the all-but-unknown Y2K-era rock band Luna Halo, who previously opened for Hoobastank. Her Fearless version sounds practically nothing like their original (though both name-check .38 Special’s Eighties classic “Caught Up in You“). In fact, it’s tough to fathom how she heard the original as raw material she could use – now that’s ears.Best line: “In the middle of the night when I’m in this dream/It’s like a million little stars spelling out your name.”

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?”

She makes a daring leap into the hair-metal mom market by teaming up with Def Leppard on CMT Crossroads, a move that works almost frighteningly well. Peak glam, especially when she asks the gender-torching question, “Demolition woman, can I be your man?”Best line: “Do you take sugar? One lump or two?”

Taylor writes her own ace lovelorn holiday standard, ambushing her ex with one of those squirm-packed Merry-Christmas phone calls. Awkward question: “When you were putting up the lights this year/Did you notice one less pair of hands?” Eat your heart out, Mariah.Best line: “I bet you got your mom another sweater.”

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. It’s immature and ridiculous, but she’s smart enough to make herself the real butt of the joke, and as usual with Swift, her self-owns are the funniest part of the song. It was understandable to tweak the “she’s better known for the things that she does on the mattress” line 13 years later, but she was already way beyond moth/flame cliches in 2010.Best line: “She thinks I’m psycho because I like to rhyme her name with things.”

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 — fifteen 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.”

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.

A sea fable that could have been inspired by her man Samuel Taylor Coleridge.Best line: “Cross your thoughtless heart / Only liquor anoints you / She’s the albatross / She is here to destroy you.”

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.”

Taylor sings back-up on a piano ballad she co-wrote with her friends in The National, a standout from their first post-Folkmore album, First Two Pages of Frankenstein. “The Alcott” is a secret meeting between two ex-lovers in a hotel bar. In the final minute, her voice takes off into a back-and-forth dialogue with singer Matt Berninger.Best line: “Everything that’s mine is a landmine.”

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.”

A folksy fingerpicking change of pace on Speak Now, pining for childhood innocence – though it feels more like a leftover from the debut. This has really grown over the years, especially when you hear her adult Taylor’s Version voice sing it.Best line: “You’re mortified your mom’s dropping you off.”

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.”

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.”

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.”

Cassandra is a natural mad-woman heroine for a Swift song: the ancient Homeric prophet, the King of Troy’s cursed daughter, with the power to see the future but not to make anyone believe her. (She knew the Greek soldiers were hiding in the Trojan Horse, but nobody listened.) The “snakes” line is the song’s only false note. But “Cassandra” poses a question many of Taylor’s narrators have asked: When everyone believes you, what’s that like?Best line: “When it’s ‘Burn the bitch,’ they’re shrieking/When the truth comes out it’s quiet.”

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.”

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.”

A delicately etched ballad about getting tangled up with an addict, as she sings, “You needed me but you needed drugs more.” It feels like a more downbeat version of “Maroon,” where a love story begins on the floor with her roommate’s cheap-ass screw-top rosé, only to go sour when the drugs take over.Best line: “If I sell my apartment / And you have some kids with an internet starlet / Will that make your memory fade from this scarlet maroon?”

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 after the heist: “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?”

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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.”

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.”

This Fall Out Boy duet came out ten years—minus a week—after Patrick Stump joined her onstage in New Jersey, on the Red Tour, for “My Songs Know What You Did In The Dark.” At first “Electric Touch” might sound like a horrific mismatch (what, Boys Like Girls were busy?) but it all explodes in the fantastic bridge, when they milk the giant proto-“Treacherous” hook, “It’s 8:05 and I see two headliiiights.” The way she turns “lights” into a ten-second song in itself? That’s our girl, kinda like the way she decides this first date is “forever” before he’s even gotten out of the damn car.Best line: “Your electric touch could fill this ghost town up with life.”

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.”

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