April 26, 2024 10:39AM

All 274 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 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 The Tortured Poets Department.

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.

From Rolling Stone US

Taylor has wept in so many bathrooms, across so many songs, but there’s something tres “New Romantics” about the way she sings, “Crying in the bathroom for some dude whose name I cannot remember now.” This Lover outtake is the flip side of Ariana’s “Thank U, Next”: she’s so grateful for this guy’s ex-girlfriends, and all the women in his past, because they taught him how to treat her. Even his mom gets high praise—“your mother brought you up loyal and kind”—which is a first in her songbook.Best line: “A heart is drawn around your name / In someone’s handwriting, not mine.”

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.”

A touching ode to the 1920s silent-film flapper Clara Bow, a Hollywood too-much too-soon legend. She was the original “It Girl”—the term was invented for her when she starred in It—only to get forgotten as soon as she was obsolete. Swift has told this kind of story many times, from “The Lucky One” to “Nothing New.” At first, the Hollywood suits say, “You look like Stevie Nicks in ’75!” But then at the end, their pitch is “You look like Taylor Swift in this light / We’re loving it / You’ve got edge / She never did.” Stevie and Taylor: truly sisters of the moon.Best line: “Crowd goes wild at her fingertips / Half moonshine, a full eclipse.”

This rowdy hell-raising saloon sing-along about a rich ex is a delightful honky-tonk jam — the kind of straight-up Nashville vibe she was about to leave behind. In the classic “Friends in Low Places” country tradition, she taunts him for his “organic shoes” and “cool indie music concerts.” Which in 2012 meant he was into the National and Bon Iver.Best line: “The girl in your bed has a fine pedigree/And I bet your friends tell you she’s better than me.”

“I Can See You” is a Speak Now vault track, but it has Red Era written all over it, a seductive early-Eighties guitar bop in the mode of the Police or the Romantics. It’s definitely not the first time she had feelings in a hallway, or the first time somebody passed her a note in secrecy, but it’s seething with lust, wit, and jacket-on-the-floor bravado. You can hear why she held it back—it might have sounded a little jarring on the same album as “Enchanted.” But what a kick to discover it now.Best line: “You won’t believe half the things I see inside my head / Wait till you see half the things that haven’t happened yet.”

A miniature aside on Tortured Poets, but a gorgeous one. Taylor always loves a story about a sad girl who finds herself the center of attention, surrounded by friends and strangers hungry for all the juicy details of how her life collapsed. “Didn’t you hear? They called it all off” is a worthy successor to “Did you ever heard about the girl who got frozen?” and “She would have made such a lovely bride, what a shame she’s fucked in the head.” Dessner’s guitar puts on the chill, as do the witchy back-up harmonies.Best line: “My beloved ghost and me / Sitting in a tree / D-Y-I-N-G.”

“Too young to know it gets better” is an empathetic hook from a songwriter just moving into her twenties. “Forever Winter” is a Red vault outtake where she’s worried about a troubled friend, wishing she could protect them from their tribulations. It makes a companion to a very different 2021 tune: her Big Red Machine single “Renegade,” another song about the mechanics of compassion.Best line: “He spends most of his nights wishing it was how it used to be/He spends most of his flights getting pulled down by gravity.”

“She’s the kind of book that you can’t put down / Like if Cleopatra grew up in a small town”—now there’s a quintessential Swift heroine. A gorgeous Speak Now vault ballad that shows how great she’s always been at observing other girls. She envies the way everyone gazes at Emma, but she sees Emma clearer than anyone else does, wishing she could be her. In so many ways, she’s singing about her future self. (Emma’s not the only one who can make the bad guys good for a weekend.) “When Emma Falls In Love” has a strong “Drops of Jupiter” vibe, which makes sense since she did a groovy cover version on the Speak Now tour. All songs about women named “Emma” rule (it’s the law) and so do all songs about Cleopatra, so this is a flawless combo.Best line: “She’s so New York when she’s in L.A.”

Taylor revisits the memory of her teenage self, with an adult sense of compassion. “Would’ve, Could’ve, Should’ve” comes on like a powerful sequel to “Dear John,” but when she sang about a similar story before, her tone was more straightforward anger and regret. This song is messier, more confused, more ambivalent, as she struggles to understand the brash, complex 19-year-old artist/superstar/mirrorball she used to be. As she reflects, “I would have stayed on my knees/And I damn sure never would’ve danced with the devil at 19/And the God’s honest truth is that the pain was heaven.”Best line: “If I was some paint, did it splatter on a promising grown man?”

A touching duet with the Dixie Chicks (their final song under their original 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 Speak Now vault song inspired by her grandparents, combining a few of her favorite stories—old photos, old couples, teen love that grows through the decades. “A crowded street in 1944” makes this sound like a sequel to both “Marjorie” and “Epiphany,” while putting “Mary’s Song” and “You Are In Love” inside an even bigger snowglobe.Best line: “I’d die for you in the same way if I first saw your face.”

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.”

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.”

“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.”

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.”

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.”

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.”

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.”

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.”

One of the most understated and least hyperdramatic moments on Tortured Poets, so easy to overlook at first, but it’s a sneakily durable gauze-rocker with heist-flick guitar twang. Taylor never can resist her Great Gatsby imagery, and she never should.Best line: “To the house where you still wait up and that porch light gleams/To the one who says I’m the girl of his American dreams.”

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.”

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.”

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.”

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“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.”

A wistful ballad on Tortured Poets, with understated production from Jack Antonoff and Patrik Berger, as she sings about spying on other people’s lives from afar. Swift has revealed she’s obsessed with the classic 1937 Old Hollywood film Stella Dallas, where Barbara Stanwyck has to stand on the sidewalk outside her estranged daughter’s wedding, watching through the window. Taylor turned that image into the final shot of the “All Too Well” film—but here, she turns it into “I attend Christmas parties from outside.”Best line: “I’m addicted to the ‘if only.’”

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.”

“I broke my own heart because you were too polite to do it”—now there’s a line that sums up a lot of chaotic Swiftian love stories. “Suburban Legends” is a witty yet regretful tune with more of her 1950s fantasies, with Taylor fantasizing about a happy ending to a long-gone high-school romance. Like other 1989 vault tracks, “Suburban Legends” sounds like it would have fit right into Midnights—so many invisible strings between those two albums, in terms of her songwriting. Best line: “You kiss me in a way that’s gonna screw me up forever.”

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.”

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 had spent 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.”

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.”

“Bejeweled” is full of late-night disco jitters, as Taylor sings about the the fear of stepping out onto the floor and putting her heart on display, until she takes the plunge because it’s scarier to think about *not* doing it. It sounds like this could be the neglected wife of “Tolerate It,” finally breaking free. (She boasts, “I polish up real nice,” as opposed to “I polish plates until they gleam and glisten.”) It’s got that “tears on the dance floor” vibe of “New Romantics,” except “New Romantics” was sung by a “we,” yet the singer of “Bejeweled” is feeling very alone indeed.Best line: “Sapphire tears on my face/Sadness became my whole sky/Some guy said my aura’s moonstone just ‘cause he was high.”

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?”

“You’re Losing Me” debuted as part of her Midnights Late Night Edition, which was available only as a physical CD, and only for sale on-site at the Eras Tour that weekend in New Jersey. (The song was later briefly available as a download.) It echoes “Epiphany,” with medics at a battlefield trying to find a pulse, except instead of a wounded soldier, it’s a dying love affair. But it all works, from Taylor’s sad sigh at the start, to her pained Joni Mitchell proverb: “You don’t know what you got till it’s gone.” “You’re Losing Me” sounds even tougher in 2024—it sounds more anything like a dry run for The Tortured Poets Department.Best line: “I wouldn’t marry me either / A pathological people pleaser.”

Taylor gave this one away to Little Big Town, who turned it into a massive 2016 country hit. “Better Man” came to loom large in her legend as a writer, so it was worth the wait to finally get her own proper version. “Better Man” hits even harder with Taylor wailing her tale of adult regret, confessing to the mirror, “The bravest thing I ever did was run.”Best line: “I gave to you my best/And we both know you can’t say that.”

A clever transitional single – great verses, grabby 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.”

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 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.”

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.”

“Lights, camera, bitch smile!” The only time Taylor goes for a dance-floor synth-disco banger on The Tortured Poets Department. It’s the flip side of “Mirrorball,” where she’s a super trooper hiding her tears from the audience because the show must go on. Jack Antonoff soups it up into an explicit homage to Vince Clarke, the synth-pop wizard of Depeche Mode, Yaz, and Erasure. As Antonoff once said, “Modern pop music should just write Vince a check for like a billion dollars for ripping him off all day long.”Best line: “I’m so depressed, I act like it’s my birthday.”

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.”

Swift returns to the story of Peter Pan and Wendy, the girl who kept waiting for him to grow up. This couple already appeared in “Cardigan” on Folklore, where Taylor sings, “Trying to change the ending, Peter losing Wendy.” But in this song, Wendy’s not trying to change him at all—she’s just moving on, the lost girl ready to find herself.Best line: “You said you’d come and get me, but you were 25/The shelf life of those fantasies has expired / Lost to the ‘Lost Boys’ chapter of your life.”

“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.

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