All 243 of Taylor Swift’s Songs, Ranked
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 243 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 1989 (Taylor’s Version).
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, Red, Speak Now, and 1989 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.
How to Watch Taylor Swift’s Acoustic ‘Folklore’ on Disney+
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“Betty” (2020)
The Betty/Inez/James love triangle is at the heart of Folklore, inspiring three of its best songs. Every aspect of “Betty” sounded designed to explode live, from the “Thunder Road” harmonica to the most shameless lighters-up key change of her career. So one of the big emotional payoffs on the Eras Tour is when she finally gets to trigger that audience chaos when she gets to Yeah I Showed Up To Your Party o’clock. (Her live version at the Academy of Country Music Awards was an arena-rock blast, for the year with no arenas.) Also love how when Taylor steps into the mind of a 17-year-old boy, the first thing she fantasizes about his male privilege is the right to make unchallenged assumptions. If James is a boy, that is. (Taylor takes care to leave it open—but has any boy in her songs ever stopped at a stoplight?) Key question: Was James in his car driving around the party listening to 1989? Because he follows all the advice she gives in “How You Get The Girl” and (surprise) it works.
Best line: “Will you kiss me on the porch in front of all your stupid friends?”
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“Begin Again” (2012)
“You said you never met one girl who had as many James Taylor records as you,” indeed. Sweet Baby Tay drops a deceptively simple ballad that sneaks up and steamrolls all over you, as an unmelodramatic coffee date leads to an unmelodramatic emotional connection. She’s always been outspoken about her mad love for her namesake JT and Carly Simon, but “Begin Again” could be the finest collabo they never wrote.
Best line: “You don’t know why I’m coming off a little shy/But I do.” Listen here.
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“Fearless” (2008)
Oh Fearless, it’s easy to take you for granted sometimes. The first time I heard her sophomore record (the record company literally played it over the phone for me because they were so afraid of it leaking) I thought, “Holy cats, this is a perfect pop album. She’ll never top this.” Then she topped it seven times in a row, to the point where it became one of history’s most curiously overlooked perfect pop albums. But Fearless has a whole new mystique ever since she chose it to kick off her remake series. The title anthem gathers so many of her favorite tropes in one chorus—rain, cars, fancy dresses, boys who stare at her while driving instead of watching the damn road, shy girls posing as brave and faking it till they make it—and builds up to a swoon. But it soars even higher now in Taylor’s Version, with all the adult soul in her voice
Best line: “You’re just so cool, run your hands through your hair/Absent-mindedly making me want you.” Listen here.
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“Getaway Car” (2017)
One of Swift’s most endearingly McCartney-esque traits is the way she goes overboard with her latest enthusiasm and starts Tay-splaining it as her personal discovery. On 1989, she informed us all what New York is; on Reputation, she breaks down the concept of “alcohol.” (Wait, you can drink beer out of plastic cups? Tell us more!) Hence “Getaway Car,” where Film Noir Tay makes her big entrance, knocking back Old Fashioneds at the motel bar, a femme fatale playing two fall guys against each other. In the glorious final minute, she decides to sell them both out and speeds off to her next emotional heist.
Best line: “Nothing good starts in a getaway car.” Listen here.
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“Cornelia Street” (2019)
A ballad about how scary it is to realize how much you have to lose — how the brand-new-crush tingle of “Holy Ground” eventually turns into the place where you have to build a life. She looks around an apartment where she’s memorized every creak in the floor, a neighborhood full of romance, and comprehends how fast it all could turn into a heartbreak hotel.
Best line: “Baby, I get mystified by how this city screams your name.” Listen here.
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“Nothing New,” With Phoebe Bridgers (2021)
Taylor and Phoebe are the Ghostface and Raekwon of the Sad Girl agenda — two kindred spirits blending their voices for a mournful guitar ballad of getting older, losing your novelty, but still crying in your bedroom. “Nothing New” is the vault track everybody was fiending for from Red (Taylor’s Version) — but it’s even better than we were hoping. The eternal question: “How can a person know everything at 18, and nothing at 22?” As you can tell from Folklore, Evermore, and Punisher, these two know the ingenue blues inside out. Can we please get a whole Taylor-Phoebe duet album?
Best line: “They tell you when you’re young/‘Girls, go out and have your fun’/Then they hunt down and kill the ones who actually do it.”
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“Cardigan” (2020)
The sweater left behind under someone’s bed, like the lost scarf in “All Too Well” or the lost glove in “It’s Nice To Have a Friend.” (Or the ex-wife’s dress left in the closet in Fiona Apple’s “Ladies”?) Swift sorts through the memories that go with breathing in the scent of a remembered lover, over brooding piano. “I knew you, leaving like a father, running like water” sure jumps out of the song, as startling as the “careless man’s careful daughter” in “Mine.” The day she wrote this song with the National’s Aaron Dessner, she posted a photo with the caption, “Not a lot going on at the moment.” Why do we ever believe a word she says?
Best line: “Chase two girls, lose the one / When you are young they assume you know nothing.”
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“Our Song” (2006)
The hit that made me a Swift fan, the first moment I heard it in 2007 – it knocked me sideways in the middle of lunch. (The CW played it as interstitial music between afternoon reruns of the Clueless sitcom and What I Like About You.) “Our song is a slamming screen door,” what a genius hook. I Googled to see who wrote this; it turned out the songwriter was also the singer and – how strange – she was just starting out. I hoped she might have at least another great tune or two in her. This song and that voice have kept slamming those screen doors ever since.
Best line: “We’re on the phone, and you talk reeeeeal slow/’Cause it’s late and your mama don’t know.” Listen here.
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“Evermore” (2020)
Taylor’s title tracks are usually bangers, but “Evermore” is a pensive piano meditation where she sits alone by the fireside, trying to figure out how it all went so wrong. We know Tay grew up a hardcore Def Leppard fan, so it’s no surprise the piano here echoes “Hysteria,” their saddest and most proto-Swiftian hit. (She sang a fantastic “Hysteria” with them on CMT in 2008.) Bon Iver’s Justin Vernon joins for the call-and-response bridge. Love the half-chuckle in the line “it was real enough to get me through”: the closest she comes to one of her Taylor Laughs in the Folklore/Evermore era.
Best line: “I rewind the tape, but all it does is pause.”
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“Red” (2012)
The mission statement for Red, this century’s most ridiculously masterful megapop manifesto. Eurodisco plus banjos – the glitter-cowgirl totality Shania Twain spent years trying to perfect, with a color-tripping lyric worthy of Prince Himself, faster than the wind, passionate as sin. Plus, her all-time gnarliest pileup of Swiftian metaphors. (Nitpick: What kind of crossword puzzle has no right answer? What self-respecting puzzlemaster would sign off on that?)
Best line: “Lovin’ him is like driving a new Maserati down a dead-end street.” Listen here.
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“Is It Over Now?” (2023)
These 1989 (Taylor’s Version) vault songs are a revelation—4 of the 5 would have been highlights on the original album. But “Is It Over Now?” looms over them all—her greatest vault stunner yet. It sounds like it’s part of a trilogy with “The Archer” and “Labyrinth,” as that spooky synth-drone intro leads into a brooding powerhouse mediation on love and loss. (If we’d heard this song in 2014, it might have been less shocking to hear “The Archer” 5 years later.) Taylor travels back and forth in time, finding different angles to look back at a youthful romance that crashed like a snowmobile. The story is full of blue eyes, blue dresses, red blood, blouses, couches, boats, the jet-set distance of “Come Back…Be Here” and the scarlet letter of “New Romantics” and the NYC coffee of “Holy Ground.” This guy turns on the charm for “unsuspecting waiters,” just like the guy in “All Too Well” charms her dad like a talk-show guest. But it all comes down to a heartbreak that these four blue eyes didn’t want to see coming. What a massive song.
Best line: “Let’s fast-forward to 300 takeout coffees later.” -
“Last Kiss” (2010)
Toward the end of Speak Now, when you’re already wrung out from sad songs and begging for mercy, this six-minute quasi-doo-wop ballad creeps up on you to inflict more punishment. So sparse, so delicate, flattering every tremor of her voice. The original “Last Kiss” seemed too perfect to be improved—but she hits it even harder on Taylor’s Version, with thirteen extra July 9ths worth of heartache in her voice, suffering through every detail of the story.
Best line: “I’m not much for dancing, but for you I did.” Listen here.
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“‘Tis the Damn Season” (2020)
A Hollywood girl who’s too shiny for her tiny hometown — the loudest woman this town has ever seen — comes back for the holidays, staying with her parents, and falls right back into the arms of the boy she left behind. Dorothea realizes she doesn’t really fit in either place, but she’ll soon be heading back to her bitch-pack of fair-weather friends in L.A. The best U2-style guitar on a Swift song since “State of Grace.” On the Eras Tour, “’Tis the Damn Season” kicks off the Evermore block, and it’s an astoundingly great stadium-quaker.
Best line: “The road not taken looks real good now/Time flies, messy as the mud on your truck tires.”
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“Snow On The Beach” feat. Lana Del Rey (2022)
“Weird but fucking beautiful,” indeed. “Snow On The Beach” is a duet with Lana Del Rey, although it sounds all the way Swiftian vocally, lyrically, and (especially) melodically. The most beguiling tune on Midnights, with pizzicato strings and lines about falling for a lover bright enough to burn out your periphery. That melody is damn near impossible to dislodge from the skull, especially that soft “it’s coming down, it’s coming down” at the end.
Best line: “Life is emotionally abusive.” -
“Champagne Problems” (2020)
In the Swiftian universe, girls have fathers — and extremely heavy relationships with them — but boys rarely have mothers. The guy in this song has a mom and a sister — you have to go back to the scarf in Maggie Gyllenhall’s closet to find a guy with either one, let alone both. The sister in “Champagne Problems” gets only one line, but she’s the one with the actual champagne. (What can it mean that “Our Song,” one of her first hits, still has her scariest boyfriend’s-mama character?) So it’s fitting Taylor echoes the “All Too Well” piano chords for this tale, where a woman responds to her college boyfriend’s marriage proposal by blowing up her life along with his. She sees herself through the eyes of his family, their dorm friends, his hometown skeptics — but she realizes she can’t see herself in this picture at all.
Best line: “She would have made such a lovely bride/What a shame she’s fucked in the head.”
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“Ours” (2010)
Like so many of her songs, “Ours” sounds like it could be channeling the 16-blue mojo of the Replacements’ punk-rock bard Paul Westerberg. (Melodically, it evokes “When It Began,” though it feels more like “I Will Dare.”) Especially the best line, which is possibly the best-est “best line” on this list, and which I sing to myself a mere dozen times a day.
Best line: “Don’t you worry your pretty little mind/People throw rocks at things that shine.” Listen here.
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“Seven” (2020)
Two little girls in the Pennsylvania woods, trying and failing to understand each other. It’s a lost childhood bond (maybe same one from “It’s Nice to Have a Friend”?), from the perspective of a kid too young to recognize that her friend’s angry dad is the ghost in their family’s haunted house. (The traumatizing fathers on Folklore are a plotline in themselves.) The little girls dream of escaping, running away to be pirate twins, but there’s no resolution — just a mystery that gets more confusing she tries to live with it.
Best line: “Please picture me in the weeds, before I learned civility.”
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“The Archer” (2019)
“The Archer” is the ultimate Goth Tay powerhouse: obsessed with revenge and guilt, shooting poison arrows into her own heart, still trying to settle the score after the battle’s over. She’s an emotional Arya Stark who never gets to cross any names off her list, because she always needs to get in one more stab. (Taylor would be wiping the blood off her sword saying, “Oh, and another thing.” That’s why we relate, right?) One of the most hair-raising moments in her music: when she switches from “they see right through me” to “I see right through me!”
Best line: “All of my heroes die all alone / Help me hold on to you.” Listen here.
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“We Are Never Ever Getting Back Together” (2012)
Like, ever. Her funniest breakup jam, because it’s her most self-mocking. She could have made the guy in this song a shady creep—a cheater, a liar, a scarf-stealer, etc. But, no, he’s just a needy little run-of-the-mill basket case, exactly like her, making the same complaints about her to his own bored friends, though his complaints can’t be as catchy as this chorus. And the video is a gem, especially when she’s wearing the Tay Is Seriously Mad Now glasses. Where is that indie-rock bar that still has a pay phone?
Best line: “And I’m like, I mean, this is exhausting, OK?” Listen here.
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“Maroon” (2022)
A New York romance where all the heartache she feared in “Cornelia Street” comes true, leaving her haunted by a love that was burning red. At first, she’s dancing barefoot, drinking on the roof, asking, “How’d we end up on the floor anyway?/You say, ‘Your roommate’s cheap-ass screw-top rosé, that’s how.’” The lovers celebrate having this big wide city all to themselves. But after it falls apart (in the usual way), she’s surrounded by the wreckage. All the different shades of maroon appear in her dreams — the wine stain on her t-shirt, the sunset, the funeral carnations, the lips she used to call home. “Maroon” has some of Taylor’s most pained singing on Midnights, especially when she sighs, “I awake with your memory over me/That’s a real fucking legacy.” “Maroon” feels so linked to “Bigger Than The Whole Sky” — ballads about how mourning can feel like both a blessing and a curse.
Best line: “When the morning came/We were cleaning incense off your vinyl shelf.” -
“New Year’s Day” (2017)
What a twist: the one-time poet laureate of teen crushdom turns out to be even sharper at adult love songs. “New Year’s Day” is her hushed piano-and-guitar ballad about two people waking up the morning after the party and getting back to the reality they share together. It captures the romance of mundane domestic details – sweeping up the glitter, rinsing out bottles, realizing this total nothing of a day is a memory you will cherish long after you’ve both forgotten the party. This is the kind of song she could keep writing into her forties and fifties.
Best line: “Please don’t ever become a stranger whose laugh I could recognize anywhere.” Listen here.
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“This Is Me Trying” (2020)
How rude of Ms. Swift to write a song so full of lines I need to get carved on my tombstone — except it would take three or four tombstones to hold them all. The easiest Folklore song to underrate, because it seems so deceptively straight-ahead. But as in “Mirrorball,” the album’s other try-try-try song (also the other “I want you to know” song), her vocal goes right to the heart. Love the deadpan way she shrugs “I have a lot of regrets about that,” plus her very on-brand decision to sing the song in somebody’s doorway. “I was so ahead of the curve, the curve became a sphere” — what a math flex. Fact: Taylor could have invented geometry, but Euclid couldn’t have written this song.
Best line: “They told me all of my cages were mental/So I got wasted like all my potential.”
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“Coney Island” (2020)
Twelve miles from Cornelia Street, but it feels a lifetime away. “Coney Island” is her duet with the National, trading verses with singer Matt Berninger, for an Evermore highlight that picks up the story from Folklore. “Coney Island” sounds like the “August” girl left her small town, forgot about James and Betty, moved to New York, found a hipster boy, figured everything would be different in the big old city, then found herself stuck in the same old story all over again. When you’re a grown-up, they assume you know nothing.
Best line: “We were like the mall before the Internet/It was the one place to be/The mischief, the gift-wrapped suburban dream.”
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“Labyrinth” (2022)
Not the flashiest song on Midnights — there’s no fancy metaphor, no razzle-dazzle wordplay, no plot, no clever twist. Just her most painfully gorgeous melody, massive in its simplicity. Taylor spends most of “Labyrinth” just sighing, “Uh oh, I’m falling in love,” over neon synths that flicker and splutter like the circuits are melting down. She doesn’t lean on poetics here — the word “labyrinth” appears only once, when she sighs, “Lost in the labyrinth of my mind.” It’s one of Jack Antonoff’s craftiest productions — loads of Brian Eno circa Another Green World. Every “uh oh” and “oh no” hits so hard—she slides into each one from a different angle. If you’re ever in the mood to forget about Taylor the songwriter and just savor her as one of pop’s most brilliant vocalists, “Labyrinth” is one to cherish. It takes some nerve for her to use this Borgesian title for such a deceptively minimal tune, but this is a lavender labyrinth you can get happily lost in. A stealth classic.
Best line: “Breathe in, breathe through, breathe deep, breathe out.” -
“Clean” (2014)
Love is the drug. “Clean” is the stark synth-folk ballad of an infatuation junkie struggling through some kind of detox, with a big assist from Imogen Heap. An intense finale for the all-killer homestretch of 1989.
Best line: “Ten months sober, I must admit/Just because you’re clean don’t mean you don’t miss it.” Listen here.
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“The Last Great American Dynasty” (2020)
There goes the loudest woman this town has ever seen. So many heroic witches, widows, crones, and madwomen on Folklore, but this one steals the show. “The Last Great American Dynasty” initially seemed more a gimmick than a song, with a clever twist that would wear off fast. But the intricate details just grow over time — melodically, production-wise, most of all vocally. Taylor’s in a haunted house where Rebekah is just one of the madwomen in the attic, and the ghosts make her feel right at home. Imagine singing “marvelous” in one song in 2012, tucking the word in your back pocket for the revenge sequel, then waiting eight years for the right moment to play that ace. Dali or no Dali, this woman will never lose a card-game bet in her damn life.
Best line: “I had a marvelous time ruining everything.”
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“The Great War” (2022)
One of the stellar Aaron Dessner collaborations tucked away on the Midnights 3 A.M. Edition. “The Great War” comes clean about the side of Taylor who only wants love if it’s torture, going into the question of how emotional battles happen and how to end them, especially when you realize you’re the one firing the cannons. It’s a dilemma she’s written about honestly her whole career, from her teen ballad “Cold As You” (“I start a fight because I need to feel something”) to “Afterglow.” The World War One imagery and martial drums are fitting for a song about how easy it is for two hearts to dig themselves into trenches. But “The Great War” also doubles as a tribute to the type of lover who can help rescue you from your own destructive instincts, the kind you want on your side.
Best line: “My knuckles were bruised like violets/Sucker-punching walls/Cursed you as I sleep-talked.” -
“Enchanted” (2010)
The moment where this bittersweet symphony leaps from a nine to a 10 comes at the 4:25 point, when it feels like the song has reached its logical conclusion, until the Interior Monologue Voice-Over Taylor beams in to whisper: “Please don’t be in love with someone else/Please don’t have somebody waiting on you.” In the final seconds, for the coup de grace, she duets with herself.
Best line: “The lingering question kept me up/ 2 a.m, who do you love?” Listen here.
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“Fifteen” (2008)
“In your life you’ll do things greater than dating the boy on the football team / I didn’t know that at 15.” Still south of her twenties, she sings her compassionate, sisterly yet hard-ass advice to her fellow teenage girls. (Spoiler: boys are always lying about everything.) Childhood pal Abigail Anderson will always be her coolest BFF of all time; Taylor was a bridesmaid in her wedding just a few years ago.
Best line: “We both cried.” Listen here.
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“Holy Ground” (2012)
Nobody does zero-to-60 emotional peel outs like our girl, and “Holy Ground” is her equivalent of Evel Knievel jumping the Snake River Canyon. Note the sly brilliance of how she steals that Eighties guitar riff from none other than Billy Idol, making this her “White Wedding” as well as her “Rebel Yell.” (Though the lyrics are about dancing with herself.) A highlight on the Red tour, showcasing Tay’s drum-solo skills.
Best line: “Hey, you skip the conversation when you already know.” Listen here.
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“Bigger Than The Whole Sky” (2022)
It’s rare to hear Taylor begin a song by admitting she’s at a loss for words — and mean it. But that’s what makes “Bigger Than the Whole Sky” so powerfully understated. It’s a twangy grief ballad, burrowing into the elegiac Mazzy Star vibe of “Sad Beautiful Tragic,” ten years after it was a forgotten highlight of Red. She mourns a goodbye that came too soon, without trying to describe what’s been lost or what kind of future is ending. But Jack Antonoff’s slide guitar eloquently fills in for all the missing details. At the end, she tries to rationalize her loss by shrugging that “it’s not meant to be,” but then rips that cliché apart as a lie she refuses to believe. Some things are meant to be, but aren’t, and those can be the toughest to mourn.
Best line: “Every single thing I touch becomes sick with sadness.” -
“Right Where You Left Me” (2021)
Okay, so we already know Taylor gets a kick out of leaving great songs off the album — but this is ridiculous. Maybe even criminal. Yet perhaps “Right Where You Left Me” had to be a bonus track on Evermore, because hearing this song once means putting it on repeat and shutting down the flow of the album. A decade after Taylor was feelin’ 22, she gets trapped in 23, reliving the moment she got her heart broken, still sitting in that restaurant. (The same one where they had their first date in “Begin Again”?) Every time she gulps “you left me noooo,” it sounds more desperate, riding Aaron Dessner’s obsessive banjo hook. She feels paralyzed in the past, but his banjo keeps urging her to get running while she can. “Right Where You Left Me” is the only Swift song with an actual cry for help — twice — and it’s a startling sound. Repeat: she left this off the album.
Best line: “Did you ever hear about the girl who got frozen?/Time went on for everybody else, she won’t know it/She’s still 23, inside her fantasy, how it was supposed to be.”
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“Cruel Summer” (2019)
For the first 98 seconds, “Cruel Summer” is merely a perfect Taylor Swift song. Then for the bridge, she takes off into a deranged greatest-hits album’s worth of choruses from brilliant songs she hasn’t written yet. You could write a whole dissertation on the erotics of windows in Taylor’s songs — no poet since Keats has been so obsessed with the kind of desire that doesn’t dare use the door. “Cruel Summer” is about sneaking around and feeling ashamed of her secrets, but also feeling proud of how ashamed she is, until she finally yells her dirtiest secret out loud: “I love you — ain’t that the worst thing you ever heard?” But make no mistake, she loves her secrets more than she’ll ever love this paramour.
Best line: “I snuck in through the garden gate / Every night that summer just to seal my fate.” Listen here.
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“Dear John” (2010)
A slow-burning, methodical, precise, savage dissection of a failed quasi-relationship, with no happy ending, no moral, no solution, not even a lesson learned – just a bad memory filed away. “Dear John” might sound like she’s spontaneously pouring her heart out, but it takes one devious operator to make a song this intricate feel that way. (“You are an expert at sorry and keeping lines blurry and never impressed by me acing your tests” – she makes all that seem like one gulp of breath.) Every line stings, right down to the end when she switches from “I should have known” to “You should have known.”
Best line: “I’m shining like fireworks over your sad empty town.” Listen here.
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“Marjorie” (2020)
The centerpiece of Evermore, an album full of haunted houses and eloquent ghosts. Taylor sings about her late grandmother Marjorie Finlay, an opera singer who used to play the San Juan supper clubs, with the key line, “If I didn’t know better/I’d think you were singing to me now.” Her hushed voice tells the story over pulsing vintage synths, in the minimalist mode of Steve Reich’s Music for 18 Musicians. At the end, she samples Marjorie’s soprano voice. A song about getting to know your loved ones better after they’re gone, giving them a home in your memory, turning their lives into folklore and passing them on like folk songs.
Best line: “Never be so kind you forget to be clever/Never be so clever you forget to be kind.”
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“Blank Space” (2014)
A double-venti celebration of serial monogamy for Starbucks lovers everywhere, as Tay zooms through the whole cycle – the high, the pain, the players, the game, magic, madness, heaven, sin. Every second of “Blank Space” is perfect, from the pen clicks to the “nasss-taaaay-scarrr” at the end. The high might not be worth the pain, but this song is.
Best line: “Darling, I’m a nightmare dressed like a daydream.” Listen here.
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“Lover” (2019)
Ladies and gentlemen, will you please stand? This bombshell is the kind of twangy guitar ballad people thought she didn’t feel like writing anymore, except she’s celebrating the kind of adult passion people assumed wasn’t melodramatic enough for her to bother singing about. But when she hits those high notes in the chorus, it’s like the sensation at the top of the roller coaster when you realize you’re zooming all the way down. “Lover” sounds like a sequel to “Last Kiss,” but with a decade’s worth more soul going into it. She reclaims the cringiest noun in the language and makes it credible for the first time since Prince sang, “I Wanna Be Your Lover.” Great video too, especially when she goes into Sad Blue Violin Pluck mode. Imagine ending your twenties with a song this masterful. Imagine heading into your thirties the same way.
Best line: “With every guitar-string scar on my hand.” Listen here.
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“Long Live” (2010)
This is her “Common People,” her “Born to Run,” her “We Are the Champions.” An arena-slaying rock anthem to cap off Speak Now, for an ordinary girl who suddenly gets to feel like she rules the world for a minute or two. “Long Live” could be a gang of friends, a teen couple at the prom, a singer addressing her audience. But like so many songs on Speak Now, her secret prog album, it reaches the four-minute point where it feels like it’s over and she’s bringing it in for a landing – except that’s when the song gets twice as great. In the final verse, she makes a gigantic mess. (Actual lyric: “Promise me this/That you’ll stand by me forever.” WTF, girl, you were doing so well there.) Yet that’s the moment that puts “Long Live” over the top – a song nobody else could have written, as she rides those power chords home. That’s Taylor: always overdoing it, never having one feeling where six would do. Long live.
Best line: “I had the time of my life fighting dragons with you.” Listen here.
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“August” (2020)
“August” feels like such a simple tune, yet it’s one of the craftiest creations in the Swiftian Multiverse. She mourns a summer fling that slipped away like a bottle of wine, over Nineties soft-rock guitars, full of Mazzy Star/Cranberries “late afternoon set at Lilith Fair” energy. (Also, that “do you remember?” at the end seems to beam in straight from LFO’s ‘Summer Girls” — the mark of a truly obsessive pop music scholar.) She tries to kid herself it’s enough to live for the hope of it all, but she keeps running over her same memory again and again, trying to make it add up to something different. It all explodes in the giddy moment at the end, when you think the song is over, and you think she’s finally going to drive away with her head held high, but she circles back for one more “get in the car!” She might sit there alone behind the mall all night, waiting for a lover she knows won’t show up, but she makes it sound like the most romantic possible place to be.
Best line: “So much for summer love and saying ‘us’/Because you weren’t mine to lose.”
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“Delicate” (2017)
“Is it cool that I said all that?” A little late for that question, Tay. But “Delicate” is her triumph, a whispery vocoder rush that sums up everything she’s about. She steals away for a late-night hoodie-shrouded rendezvous at her local dive bar, trying to play jaded and cool. But because she’s Taylor, she can’t stop constantly pointing out how chill she’s being, elbowing you in the ribs with those “isn’t it? isn’t it?” chants. (I count 24 “isn’t it”‘s in this song and I am feeling every one of them.) She spends “Delicate” talking herself out of that midnight confession, but when it spills out — “I pretend you’re mine all the damn time” – the moment feels cataclysmic. As ever, the girl sets strict emotional rules for herself and then trashes them all. Let’s face it, Tay will always fail spectacularly at playing it cool, because she will never be able to resist saying way too much of All That. Yet as “Delicate” proves, All That is what she was born to say. Isn’t it?
Best line: “Is it chill that you’re in my head?” Listen here.
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“Mirrorball” (2020)
Taylor shines like the disco ball gazing down on the dance floor, wondering why everybody else looks so confident and imagining how that feels. A seething ballad about a loner feeling a little too loud and a little too bright, afraid everyone’s staring at her flaws yet feeling invisible anyway. “Mirrorball” revisits the party vibe of “New Romantics” from another angle, with Taylor twirling on high heels, spinning like a girl in a brand new dress, hating herself for being so desperate to sparkle for strangers. This is the kind of vulnerable teen sensibility that got her started writing songs in the first place (i.e. most of her debut album). But in classic Swift style, she decides exactly what she’s going to allow herself to feel, then wonders why she feels the exact opposite. She’s the same girl in the swing from “Seven,” grown up yet still feeling like she’s dangling in mid-air, never touching ground. Who else has a songwriting mind like this? Queen of Concept.
Best line: “I’m still a believer but I don’t know why / I’ve never been a natural, all I do is try, try, try.”
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“New Romantics” (2014)
The way Taylor exhales at the end of the line “I’m about to play my ace-aaah” is perhaps the finest moment in the history of human lungs. “New Romantics” is where she takes the Eighties synth-pop concept of 1989 to the bank, with a mirror-ball epiphany that leaves tears of mascara all over the dance floor. She tips her cap to the arty poseurs of the 1980s New Romantic scene – Duran Duran, Adam Ant, the Human League, etc. – yet sounds exactly like her own preposterously emotional self. (One of my weirdest moments of recent years: explaining this song’s existence to the guys in Duran Duran.) “New Romantics” is hardly the first time she’s sung about crying in the bathroom, but it’s the one that makes crying in the bathroom sound like a bold spiritual quest, which (when she sings about it) it is. The punch line: Having written this work of genius, exceeding even the wildest hopes any fan could have dreamed, she left it off the damn album, a very New Romantic thing to do.
Best line: “We show off our different scarlet letters/Trust me, mine is better.” Listen here.
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“All Too Well” (2012-2021)
So casually cruel in the name of being awesome. This towering ballad is Swift’s zenith, building to peak after peak. For “All Too Well,” she teams up with her songwriting sensei Liz Rose to spin a tragic tale of doomed love and scarves and autumn leaves and maple lattes. And her greatest song just got even greater in the definitive 10-minute version, with Taylor digging up her lost verses, to bring it to a whole new level of All Too Unwell. What kind of artist takes her own masterpiece and tears it all up? This one. Only this one. Result: an even bolder masterpiece.
Every version of “All Too Well” tells a different story. There’s the “Sad Girl Autumn” version from Long Pond Studio, with Aaron Dessner on piano. The acoustic-guitar solo version from the theater premiere for her short film. But each version feels like it’s all her, because this isn’t really a song about a boy — never was. It’s about a girl, her piano, her memory, and her refusal to surrender her most painful secrets, even when it’s tempting to forget.
It’s full of killer moments: the way she sings “refrigerator,” the way she spits out the consonants of “crumpled-up piece of paper,” the way she chews up three “all”’s in a row. No other song does such a stellar job of showing off her ability to blow up a trivial little detail into a legendary heartache. That scarf should be in the Rock & Roll Hall of Fame, though in a way it already is. You can schaeden your freude all over the celebrity she reputedly sings about, but on the best day of your life you will never inspire a song as great as “All Too Well.” Or write one.
Best line: “Maybe we got lost in translation/Maybe I asked for too much/Maybe this thing was a masterpiece till you tore it all up/Running scared, I was there, I remember it all too well.” Listen here.