Taylor Swift's Songs: All Ranked by Rob Sheffield - Rolling Stone
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All 153 of Taylor Swift’s Songs, Ranked

From teen country tracks to synth-pop anthems and rare covers, a comprehensive assessment of her one-of-a-kind songbook through ‘Lover’ era

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 153 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 ingénue right up to Lover. Every fan would compile a different list – that’s the beauty of it. 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.)

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.

Taylor Swift41ST ANNUAL ACADEMY OF COUNTRY MUSIC AWARDS, LAS VEGAS, NEVADA, AMERICA - 23 MAY 2006

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151

“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.”

Taylor Swift - Christmas Must Be Something More

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150

“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?”

Taylor Swift - Only Me When I'm With You
149

“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.”

Taylor Swift - Two Is Better Than One

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148

“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.”

Taylor Swift - Silent Night

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147

“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.”

Taylor Swift - Both Of Us
146

“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.”

Taylor Swift - The Last Time

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145

“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.”

Taylor Swift - ME!
144

“ME!” (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!”

Taylor Swift - The Outside

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143

“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?”

Taylor Swift - Girl At Home

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142

“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.”

Taylor Swift - Come In With Rain

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141

“Come in With the Rain” (2008)

She leaves her window open overnight, just in case her ex falls out of a cloud. There’s a great “oooh” in the second chorus – one of those moments you can tell she’s an Oasis fan. (This song makes you suspect “Don’t Look Back In Anger” is a fave.)

Best line: “I could stand up and sing you a song/But I don’t wanna have to go that far.”

John Mayer and Taylor Swift - Half Of My Heart

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140

“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.”

Taylor Swift - Other Side Of The Door

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139

“The Other Side of the Door” (2008)

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.

Best line: “Me and my stupid pride are sitting here alone / Going through the photographs, staring at the phone.”

Taylor Swift - Superman

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138

“Superman” (2010)

A Lois Lane fantasy, left off Speak Now for good reason.

Best line: “Tall, dark and beautiful/He’s complicated, he’s irrational.”

Taylor Swift - Cold As You

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137

“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.”

Taylor Swift - If This Was A Movie

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136

“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!”

Taylor Swift - Sweeter Than Fiction

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135

“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.”

Taylor Swift - A Perfectly Good Heart

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134

“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?”

Taylor Swift - White Christmas

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133

“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.”

Taylor Swift - I Don't Wanna Live Forever
132

“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.”

Taylor Swift - Marys Song
131

“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.”

Taylor Swift, Keith Urban and Tim McGraw - Highway Don't Care

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130

“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.”

Taylor Swift - Change
129

“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.”

Taylor Swift - Nashville

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128

“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?”

Taylor Swift - Sweet Escape

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127

“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.”

Taylor Swift - I'd Lie

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126

“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.”

 

Taylor Swift - Look What You Made Me Do
125

“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.

Taylor Swift - Never Grow up

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124

“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.

Best line: “You’re mortified your mom’s dropping you off.”

Taylor Swift - Stay Beautiful

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123

“Stay Beautiful” (2006)

An early stab at a take-the-high-road breakup song.

Best line: “He whispers songs into my window.”

Taylor Swift - I Want You Back

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122

“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.”

Taylor Swift - End Game
121

“End Game” (ft. 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.”

Taylor Swift - September

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120

“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.”

Taylor Swift - The Way I Loved You

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119

“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.”

Taylor Swift - Thug Story
118

“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.”

Taylor Swift - I Wish You Would

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117

“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.”

Taylor Swift - Umbrella

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116

“Umbrella” (2007)

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.”

Taylor Swift and Kenny Chesney - Big Star

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115

“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.

Best line: “She signed autographs like she was Garth Brooks in a skirt.”

Taylor Swift - I Forgot That You Existed

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114

“I Forgot That You Existed” (2019)

Subtitle: “So I Sang About You First Thing On My New 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.”

Taylor Swift - I Heart ?

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113

“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.”

Taylor Swift - Can't Stop Loving You

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112

“Can’t Stop Loving You” (2019)

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.”

Taylor Swift - Breathe

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111

“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.”

Taylor Swift - The Moment I Knew

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110

“The Moment I Knew” (2012)

A somber piano ballad about getting stood up on your 21st birthday.

Best line: “There in the bathroom/I try not to fall apart.”

Taylor Swift - Untouchable

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109

“Untouchable” (2009)

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.”

Taylor Swift and Def Leppard - Pour Some Sugar

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108

“Pour Some Sugar On Me” With Def Leppard (2008)

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 Swift - Christmases When You Were Mine

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107

“Christmases When You Were Mine” (2007)

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.”

Taylor Swift and Sugarland - Babe

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106

“Babe” (with Sugarland) (2018)

Taylor’s long-running babe alliance with Sugarland includes this country hit she wrote for them with Train’s Patrick Monahan. Tay does a smashing job playing the femme fatale supervillain in the Mad Men-style video, not to mention her low-key but lethal vocals.

Best line: “This is the last time I’ll ever call you ‘babe.’”

Taylor Swift - American Girl

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105

“American Girl” (2009)

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!”

Taylor Swift - Invisible

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104

“Invisible” (2006)

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.”

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