From teen country tracks to synth-pop anthems and rare covers, a comprehensive assessment of her one-of-a-kind songbook.
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 237 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 Speak Now (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 Speak Now. 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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“Bad Blood” (2014)
Melodically parched, lyrically unfinished, rhythmically clunky – this was a mighty strange pick for a single from an album as loaded as 1989. There are a million things Taylor has in common with Paul McCartney – one is that celebrity grievances tend to sound like a penny-ante waste of their time, even when they’re totally understandable (unless you’re a fan of Macca’s “Dear Boy,” where John Lennon is his Katy Perry). The single remix is improved by Kendrick Lamar – but he wasn’t saving his A-game for this one.
Best line: “Band-Aids don’t fix bullet holes.”
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“Santa Baby” (2007)
Yes, she made a Christmas album, which is full of contenders for the basement of this list. But an oldie about a gold digger wooing Little Saint Nick was perhaps a dubious pick for a singer still in her teens.
Best line: “I’ve been an awful good girl.”
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“A Place in This World” (2006)
Apprentice work from the debut, when she was still learning the ropes as a country songwriter. Yet, the seeds of greatness are already there. Historical significance: This was the song where Tay discovered rain imagery, which in her hands was the equivalent of Sir Isaac Newton inventing calculus.
Best line: “I’ll be strong/I’ll be wrong/Oh, but life goes on.”
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“Christmas Must Be Something More” (2007)
A hymn about how Jesus is the reason for the season, with the hook, “So here’s to the birthday boy who saved our lives.” Unlike most boys Swift sings about, Jesus didn’t comment publicly.
Best line: “What would happen if God never let it snow?”
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“I’m Only Me When I’m With You” (2006)
Could there be a less Swiftian sentiment? For better or worse, this girl is always herself. That’s kinda the point.
Best line: “I’m only up when you’re not down/Don’t wanna fly if you’re still on the ground.”
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“Two Is Better Than One,” With Boys Like Girls (2009)
A long, long, very long duet with former Good Charlotte and Fall Out Boy tourmates Boys Like Girls, who are either from London or Nashville (they seem to switch accents at random). For some reason, they decided to delay her entrance until a minute into the song, arguably the worst decision in the history of decisions.
Best line: “You already got me coming…undone.”
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“Silent Night” (2007)
This bizarre version manages to miss almost every single note in the melody. They sure were in a rush to get this Christmas album out.
Best line: “Shepherds quake at the sight.”
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“Macavity” (2019)
This one will be tough to explain to future generations, but here goes: So they made this Hollywood movie out of the Broadway musical Cats. Full of magic, furry, singing cats. So much fur. So much magic. Taylor plus felines — it should add up to classic cinema, right? Not quite.
Best line: “Macavity’s a mystery cat / He’s called the Hidden Paw.”
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“Both of Us,” With B.o.B (2012)
Nice try at remaking “Airplanes,” but that Hayley Williams lightning does not strike twice.
Best line: “Your money’s all gone, and you lose your whip.”
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“The Last Time,” With Gary Lightbody (2012)
Her duet with the guy from Snow Patrol. Unfortunately, their voices don’t mesh at all – what, is he auditioning for a Spandau Ballet tribute band? The funny moment is the très Eighties synth-horn blurp at the three-minute mark.
Best line: “This is the last time I’m asking you this/Put my name at the top of your list.”
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“ME!” With Brendon Urie (2019)
One of those beloved Taylor traditions: the Lead Single That Reveals Absolutely Nothing About the New Album. And for the second time in a row, it’s the weakest track by a mile. Honestly, Taylor would have released “Maxwell’s Silver Hammer” as the first single from Abbey damn Road. “ME!” is her only song title with an exclamation point, an oddity for this most !!! of singers. Even Brendon Urie sounds squeamish, and he’s the guy who once released a song called “Folkin’ Around.” As we now know, she had “Cruel Summer” in the can, but opted not to make it the summer jam of 2019 because she decided to release “ME!” instead, a decision that will be studied by Swiftian scholars for years to come.
Best line: “Hey kids, spelling is fun!”
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“The Outside” (2006)
Still a rookie, still learning, still trying to get away with “read between the lines” and “the road less traveled by” in the same verse.
Best line: “Nothing seems to work the first few times/Am I right?”
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“Hold On,” With Jack Ingram (2008)
An early country throwaway, released a decade later on Ingram’s From the Vault: Live 2007-2009. A teenage Swift chirps back-up harmony, doing the part originally sung by Sheryl Crow.
Best line: “Sign our names in the dust on your family car.”
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“Beautiful Ghosts” (2019)
She wrote this with Andrew Lloyd Webber for the Cats soundtrack — as she said, “If you can’t get T.S. Eliot, get T.S.”
Best line: “I watch from the dark, wait for my life to start / With no beauty in my memory.”
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“Girl at Home” (2012)
A perfunctory cheating-is-bad homily, with barely any chorus.
Best line: “I feel a responsibility/To do what’s upstanding and right.”
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“Half of My Heart,” With John Mayer (2009)
The real prize from his Battle Studies album is “Heartbreak Warfare”; this is lesser J.M., with an underexploited T.S. cameo and an increasingly irritating premise of hearts having fingers, which they don’t. No wonder the girl in the dress cried the whole way home.
Best line: “Half of my heart’s got a grip on the situation.”
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“Sweeter Than Fiction” (2013)
A warm-up for the synth-pop of 1989, from the One Chance soundtrack.
Best line: “What a sight when the light came on.”
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“Superman” (2010)
A Lois Lane fantasy left off Speak Now, but it gets a real upgrade with her Taylor’s Version vocal muscle.
Best line: “Tall, dark and beautiful/He’s complicated, he’s irrational.”
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“Cold as You” (2006)
“I start a fight ’cause I need to feel something” – give her credit for honesty, even in this raw phase.
Best line: “Every smile you fake is so condescending.”
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“If This Was a Movie” (2010)
“Good evening, sir. May I help you? You’re a guy in a Taylor Swift song who wants to stand outside the window in the pouring rain, begging the love of your life to forgive your sorry ass? Take a number and get in line. No, that line.”
Best line: “But I take it all back now!”
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“A Perfectly Good Heart” (2006)
“It’s not unbroken anymore”? Paging the eminent cardiologist Dr. Toni Braxton.
Best line: “Why would you wanna make the very first scar?/Why would you wanna break a perfectly good heart?”
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“White Christmas” (2007)
Unlike “Silent Night,” this was a yuletide carol she could handle, with a straight-down-the-middle country rendition.
Best line: “Where the treetops glisten.”
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“I Don’t Wanna Live Forever,” With Zayn Malik (2016)
Neither she nor Zayn sound deeply interested in this dueling-falsettos battle from the Fifty Shades Darker soundtrack. Maybe it works in the movie, but who wants to go find out? Really, they sound like two ghosts standing in the place of…sorry, sore subject, let’s drop it.
Best line: “I’ve been looking sad in all the nicest places.”
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“Mary’s Song (Oh My My)” (2006)
A through-the-years romance, with a sweet homespun touch.
Best line: “I’ll be 87, you’ll be 89/I’ll still look at you like the stars that shine in the sky.”
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“Highway Don’t Care,” With Tim McGraw and Keith Urban (2013)
A duet from McGraw’s album Two Lanes of Freedom, with a guitar solo from Keith Urban. The plot: His ex is driving away, listening to a Taylor song on the radio, as Tay tries to coax the woman into turning the car around and going home. Perhaps McGraw’s finest duet since his great lost Nelly jam, “Over and Over.”
Best line: “I bet you’re bending God’s ear talking ’bout me.”
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“Change” (2008)
Oh, the fall of 2008 – Chuck and Blair were still an item, Suede was killing it on Project Runway, and “Change” was a de facto victory song for Obama, complete with a thumbs-up for the “revolution.” Yeah, those were different times.
Best line: “These walls that they put up to hold us back will fall down.”
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“Nashville” (2011)
A cover of an obscurity by country singer David Mead, tucked away as a bonus on the Target edition of the Speak Now Tour Live DVD.
Best line: “Was that a blood or wine stain on your wedding dress?”
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“Sweet Escape” (2011)
From the same live DVD, a remake of the Gwen Stefani solo hit. Taylor’s vocal sure fits the Gwen just-a-girl sensibility.
Best line: “I must apologize for acting stank.”
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“I Want You Back” (2010)
A live acoustic tribute to the then-recently departed Michael Jackson, with a bit of Motown tremble in her voice.
Best line: “Oh darling, I was blind to let you go.”
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“Only the Young” (2019)
“Only the Young” debuted in her excellent doc Miss Americana, a synth-pop tribute to the next generation of political activists. It’s also a clever Swiftian fake-out, giving everyone a totally wrong idea of where she was headed musically — almost like she was announcing, “Nothing to see here, folks. Definitely no keepers left over from the Lover era.” Was she already plotting to catch us off guard with Folklore? Don’t put it past her. But you’d never guess she was about to make an acoustic album full of folk songs about sweaters.
Best line: “Up there’s the finish line / Our future is worth the fight.”
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“I’d Lie” (2006)
A perky early throwaway about a teenage crush, recorded for her debut and briefly released as a bonus track.
Best line: “He loves to argue, born on the 17th.”
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“Umbrella” (2008)
The Rihanna hit, briefly covered on the Live from SoHo digital album. Her finest Ri tribute remains her 2011 version of “Live Your Life” with T.I. onstage in Atlanta – sadly unreleased, but a duet that deserves to be enshrined for the ages.
Best line: “Stand under my umbrella, ella, ella.”
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“Look What You Made Me Do” (2017)
The reason fans once cared about rap beefs: they inspired great songs, whether it was Queens vs. the Bronx (“The Bridge” vs. “The Bridge Is Over” vs. “Have a Nice Day”) or LL Cool J vs. Kool Moe Dee (“How Ya Like Me Now” vs. “Jack the Ripper” vs. “Let’s Go” vs. “To Da Break of Dawn”). But this just sounds like a trivial time-waster by her standards – Swift’s celebrity feuds are not really one of the hundred most interesting things about her. The main attraction is the retro Panic! at the Disco vibe. “Look What You Made Me Do” turned out to be the lamest track on Reputation, but an impressively perverse head fake – a lead single that ended up having nothing to do with the album, musically or conceptually, making sure her new relationship songs would come as a surprise. To find a comparable stunt, you might have to go back to 1982, when Michael Jackson fooled the world into thinking Thriller was going to be a whole album of “The Girl Is Mine.”
Best line: “It’s much better to face these kinds of things with a sense of poise and rationality.” Oh wait – that actually is Panic! at the Disco.
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“Paris” (2022)
“I wanna brainwash you into loving me forever / I wanna transport you to somewhere the culture’s clever”—for Tay, that means a fantasy of Gay Paree. But the whole point of this song is that you can make your own Paris wherever you are, just by drawing your own dream map on the bedroom ceiling. And if you have an amour to share the dream with, all the better. “All the outfits were terrible, 2003 unbearable”—sounds like Taylor found somebody’s Friendster photo stash of crop tops and trucker hats. “Did you see the photos? / No, I didn’t, but thanks though” is being kind.
Best line: “Privacy sign on the door and on my page and on the whole world / Romance is not dead if you keep it just yours.”
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‘The Joker and the Queen,’ with Ed Sheeran (2022)
An Ed Sheeran ballad, refurbished into a sweet duet with his long-running favorite co-star. The video has the same actors who played Ed and Tay as little kids in the “Everything Has Changed” video — ten years later. Both singers sound right at home with the metaphor of a poker game — Ed can’t see it in her face, but she’s about to play her ace.
Best line: “I’ve been played before, if you hadn’t guessed/So I kept my cards close to my foolproof vest.”
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“September” (2018)
The Earth, Wind & Fire classic, already covered by every wedding band on the planet, becomes a mournful banjo lament. It’s her tribute to the late great Maurice White, a songwriter who shared her knack for building hits out of quirky details. (Changing “the 21st night of September” to the 28th is a very Swiftian touch.) Next she might try “That’s the Way of the World” or “After the Love Has Gone.”
Best line: “Love was changing the minds of pretenders.”
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“Stay Beautiful” (2006)
An early stab at a take-the-high-road breakup song.
Best line: “He whispers songs into my window.”
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“End Game,” with Ed Sheeran & Future (2017)
Future reaffirms her long-running bond with ATLien hip-hop, which goes back to her B.o.B. and T.I. duets. Plus her trusty wingman Ed Sheeran. She offers an update about her lipstick status (still red! good to know) and her relationship with drama: “I swear I don’t love the drama — it loves me!”
Best line: “I bury hatchets, but I keep maps of where I put ‘em.”
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“That’s When” (2021)
A Fearless outtake refurbished as a duet with her old friend Keith Urban. She pleads for forgiveness after crushing a lover’s heart for no particular reason, in the mode of “Back to December” or “Afterglow.”
Best line: “I knew my words were hard to hear/And harder to ever take back.”
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“The Way I Loved You” (2008)
She meets a low-stress boy who doesn’t want love to be torture. Alas, this suitor is toast, because he reminds her how much she misses the manic pixie drama vampire she dated before. Sorry, dude – she loves the players, and she loves the game.
Best line: “He respects my space/And never makes me wait.”
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“Thug Story,” With T-Pain (2009)
The classic T-Pain and Taylor duet from the 2009 CMT Awards, still T-Swizzle’s finest rap performance.
Best line: “No, I never really been in a club/Still live with my parents, but I’m still a thug/I’m so gangsta you can find me baking cookies at night/You out clubbing, but I just made caramel delight.”
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“I Wish You Would” (2014)
One of her many, many songs set at 2 a.m. – clearly the most inspiring hour on Swift Standard Time – with a staccato disco guitar lick.
Best line: “We’re a crooked love in a straight line down.”
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‘All Of The Girls You Loved Before’ (2023)
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.”
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“Big Star,” With Kenny Chesney (2017)
“This song is about a girl who had a dream and followed it,” Kenny Chesney tells the roaring Nashville crowd. One of those girls jumps onstage to sing along. “My friend Taylor Swift showed up on my birthday to surprise me,” Kenny explained. “In a lot of ways, that song and that lyric is Taylor’s journey.” Their touching “Big Star” duet came out on his concert album Live from No Shoes Nation — 10 years after he gave this rookie a break as the opening act on his 2007 summer tour. There is no loyalty like Swift loyalty.
Best line: “She signed autographs like she was Garth Brooks in a skirt.”
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“I Forgot That You Existed” (2019)
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.”
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“I Heart ?” (2008)
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.”
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“Gasoline (Remix),” With Haim (2020)
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?”
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“Breathe” (Ft. Colbie Caillat) (2008)
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.”
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“Untouchable” (2008)
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.”
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“Never Grow Up” (2010)
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.”