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 Swift - Safe And Sound
53

“Safe and Sound” With the Civil Wars (2012)

She ventures into rootsy folkie territory on the Hunger Games soundtrack, teaming up with the Civil Wars and producer T Bone Burnett, exploring crevices of her voice she hadn’t opened up before. Everyone steps out of their comfort zone, and it works. The Swift-Burnett connection raises the question of how long it’ll take her to collaborate with Elvis Costello, a songwriter with whom she shares some fascinating affinities. At the very least, Tay should cover “New Lace Sleeves.”

Best line: “Don’t you dare look out your window, darling/Everything’s on fire.”

Taylor Swift - Soon You'll Get Better

Dave Hogan/ABA/Getty Images

52

“Soon You’ll Get Better” With the Dixie Chicks (2019)

A touching duet with the Dixie Chicks 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.”

Taylor Swift - Ronan

Dave J Hogan/Getty Images

51

“Ronan” (2012)

A little-known charity single for cancer research, unlike anything else in her songbook. She wrote this about Ronan Thompson, a four-year-old Arizona boy who died of neuroblastoma, after she read his mom’s blog. She turned the blog entries into a disarmingly eloquent ballad (crediting Maya Thompson as co-writer) and performed “Ronan” at the Stand Up to Cancer benefit. You might expect it to be manipulative and obvious; it isn’t.

Best line: “We had our own secret club.”

Taylor Swift - Picture To Burn
50

“Picture to Burn” (2006)

The dawn of Petty AF Tay, as she serves her ex beatdown threats. Every boy who ever complained when Taylor wrote about him – this is where you officially got fair warning.

Best line: “Watch me strike a match on all my wasted time.”

Taylor Swift - You Need To Calm Down
49

“You Need to Calm Down” (2019)

The first time I heard “Welcome to New York,” back in 2014, I thought people would freak out over the explicit pro-queer lyrics. (“Boys and boys and girls and girls” — she was not afraid to burn her bridges.) But of course, people slept on it. So I love how she just did it a little louder for the people in back. Eighties New Wave synth-pop was one of the gayest musical movements ever, but at the time, it was all hidden — virtually none of the genre’s (many) queer artists were out. So it’s fitting how her New Wave homage foregrounds the music’s LGBTQ roots. When she growls, “Damn, it’s 7 a.m.” we all know Taylor has been up pacing the floor at 2 a.m., because that’s what she does.

Best line: “Can you just not step on our gowns?”

Taylor Swift - The Best Day
48

“The Best Day” (2008)

Her tribute to Mama Swift. A weapons-grade tearjerker and not to be trifled with in a public place. NSFW, unless you are a professional crier.

Best line: “You were on my side/Even when I was wrong.”

Taylor Swift - The Story Of Us
47

“The Story of Us” (2010)

You could credit this song with single-handedly driving John Mayer out of the pop heartthrob business and into the Grateful Dead – which is just one of the things to love about it. Along with the Joey Ramone-style way she says, “Next chapter!”

Best line: “See me nervously pulling at my clothes and trying to look busy.”

Taylor Swift - How You Get The Girl

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46

“How You Get the Girl” (2014)

A seminar on girl hearts and the wooing thereof, with Coach Taylor offering a pep talk to girl-curious boys everywhere. She busts out her trusty acoustic guitar, teardrop stains and all, just to turn it into a beatbox.

Best line: “Stand there like a ghost shaking from the rain / She’ll open up the door and say ‘Are you insane?'”

Taylor Swift - Hey Stephen

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45

“Hey Stephen” (2008)

Loaded with classic girl-group flourishes, right from the opening “Be My Baby” drum beat. Plus, it begins and ends with her finest humming solos. If she wanted to hum on every song, she could make that work.

Best line: “All those other girls, well, they’re beautiful/But would they write a song for you?”

Taylor Swift - London Boy

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44

“London Boy” (2019)

Nice one, London! You have inspired a Taylor Travelogue even more over-the-top than “Welcome to New York,” with visits to Camden Market, SoHo, Highgate, and everyone’s favorite tourist destination, Hackney. As the English are so fond of saying, she over-eggs the pudding, and no wonder some skeptics got their knickers in a twist, but her Britpop tribute evokes the louche music-hall parodies of London bands from Madness to Blur. (She’s clearly been bumping Side One of Parklife.) The best part of this song is its wide-eyed enthusiasm, the least London of emotions. We desperately need one of these per album, please — maybe next time she’ll do “Paris, Je T’Aime” or “Arigato Kyoto.”

Best line: “I enjoy nights in Brixton / Shoreditch in the afternoon.”

Taylor Swift - Should've Said No

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43

“Should’ve Said No” (2006)

A pissed-off highlight of the debut, with an Oasis-worthy chorus. Savor the perfect Liam Gallagher way she milks the vowels of “begging for forgiveness at my fee-ee-eet.”

Best line: “It was a moment of weakness, and you said yes.”

Taylor Swift - White Horse
42

“White Horse” (2008)

Teen Romantic Tay meets Bitter Adult Tay in a superbly disenchanted breakup ballad that gives up on princesses and fairy tales.

Best line: “I’m not the one you’ll sweep off her feet/Lead up the stairwell.”

Taylor Swift - Teardrops On My Guitar
41

“Teardrops on My Guitar” (2006)

One of her defining early smashes – and the one that marked her crucial crossover to the minivan-mom adult audience, where country stars do most of their business. It also inspired the first anti-Taylor answer song – Joe Jonas sang, “I’m done with superstars/And all the tears on her guitar” in 2009, on the JoBros’ instantly forgotten Lines, Vines and Trying Times.

Best line: “Drew walks by me/Can he tell that I can’t breathe?”

Taylor Swift - Sad Beautiful Tragic

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40

“Sad Beautiful Tragic” (2012)

She must have heard a Mazzy Star song on the radio that morning and thought, “Hey, this sounds like fun.” All the details are in place, from her woozy Hope Sandoval mumble to the way Nathan Chapman nails Sandoval’s exact tambourine sound. Such an underrated Red gem, one she’s almost never done live. Would any other songwriter on Earth have the sheer gall to get away with that title? Let’s hope nobody tries.

Best line: “You’ve got your demons, and, darling, they all look like me.”

Taylor Swift - It's Nice To Have A Friend

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39

“It’s Nice to Have a Friend” (2019)

The most divisive track on Lover — but for those of us who cherish this song, it’s a tiny little haiku miracle. That harp. Those steel drums. That creepy Lost Boys choir. That “Moonlight Mile” guitar. The childhood vibe evokes the White Stripes’ “We’re Going to Be Friends,” but it’s all her. Also, love how this story starts with a lost glove — seven years after the lost scarf in “All Too Well.”

Best line: “Call my bluff / Call you ‘babe.’”

Taylor Swift - I Did Something Bad

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38

“I Did Something Bad” (2017)

Wait, she fell in love with a narcissist? Who saw that coming? Despite the Eurodisco bleeps and bloops, this is a total Nineties grunge-rock rager – she switches into Eddie Vedder/Scott Weiland mode when she growls that “over and over and over again if IIII could.”

Best line: “I never trust a playboy but they love me / So I fly ’em all around the world and I let them think they saved me.”

Taylor Swift - Mine
37

“Mine” (2010)

“You made a rebel of a careless man’s careful daughter” is one of those hooks where she seems to cram a whole life story into one line.

Best line: “I was a flight risk with a fear of falling.”

Taylor Swift - Wildest Dreams
36

“Wildest Dreams” (2014)

You rang, Goth Taylor? At first this might have seemed like a minor pleasure on 1989, but it really sounds stronger and stronger over the years, especially when she hiccups the words “my last request ih-is.” The video features giraffes and zebras.

Best line: “He’s so tall and handsome as hell/He’s so bad, but he does it so well.”

Taylor Swift - Daylight

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35

“Daylight” (2019)

The finale of Lover, and a passionate sequel to “Clean.” “Daylight” takes off in the final minute when she gives a soliloquy that sounds like one of those 2 a.m. voice memos you forget about until you find them on your phone weeks later. “I wanna be defined by the things I love, not the things I’m afraid of” — it’s an affirmation to believe in.

Best line: “I once believed love would be burning red, but it’s golden.”

Taylor Swift - Dress

Kevin Winter/Getty Images

34

“Dress” (2017)

Swift is no stranger to getting emo over her dresses, but this time it’s different: “Only bought this dress so you could take it off.” Her most carnal slow jam is also one of her saddest – the ache in her voice, the yearning in those synth sparkles. There’s something so “Little Red Corvette” in the way she interrupts her own wordplay with forlorn sighs. As for that golden tattoo – hold on, we’re going home.

Best line: “I don’t want you like a best friend.” Listen here.

Taylor Swift - This Love

Matt Sayles/Invision/AP/Shutterstock

33

“This Love” (2014)

A meditative 1989 nocturne – half acoustic introspection, half electro reverie – as she genuflects in the midnight hour.

Best line: “I could go on and on, on and on/And I will.”

Taylor Swift - Mean
32

“Mean” (2010)

A banjo-core Tay-visceration of people who are mean, liars, pathetic, and/or alone in life, including the ones who live in big old cities. Always a concert highlight, showcasing her murderers’ row of a band, the Agency.

Best line: “Drunk and grumbling on about how I can’t sing.” Listen here.

Taylor Swift - I Knew You Were Trouble

John Shearer/Invision/AP/Shutterstock

31

“I Knew You Were Trouble” (2012)

It slams like a lost Blondie hit, from somewhere between Parallel Lines and Eat to the Beat. The way she sings the word “drown-i-i-i-ing” alone makes it.

Best line: “He was long gone when he met me/And I realize the joke is on me.” Listen here.

Taylor Swift - Tim McGraw
30

“Tim McGraw” (2006)

We knew she was trouble when she walked in – or at least we should have guessed from her debut single. You couldn’t make this up – a nervy high school kid shows up with a country ballad she whipped together after math class one day, about slow dancing in the moonlight to the pickup truck radio: “When you think Tim McGraw/I hope you think of me.” Within a couple of years, she’s an even bigger star than McGraw is.

Best line: “He said the way my blue eyes shined/Put those Georgia stars to shame that night/I said, ‘That’s a lie.'” Listen here.

Taylor Swift - Call It What You Want

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29

“Call It What You Want” (2017)

Always here for the Taylor castle metaphors. The warmest moment on Reputation, about how exotic it feels to give up worrying about judgy strangers and start living a damn life. “Call It What You Want” celebrates a mature relationship — the kind where you turn off your phone for hours at a time and pull down the shades and risk letting yourself get a little known.

Best line: “Not because he owns me / But ’cause he really knows me.” Listen here.

Taylor Swift - Style
28

“Style” (2014)

Not always a subtle one, our Tay. This extremely 1986-sounding synth-pop groove is full of hushed-breath melodrama, where even the guy taking off his coat can feel like a plot twist. (Why would he keep his coat on? This is his apartment.) And the long-running songwriting badminton between her and Harry Allegedly is pop call-and-response the way it ought to be – no matter how much misery it might bring into their personal lives, for the rest of us it means one great tune after another.

Best line: “You got that James Dean daydream look in your eye/And I got that red lip classic thing that you like.” Listen here.

Taylor Swift - State Of Grace

Evan Agostini/Invision/AP/Shutterstock

27

“State of Grace” (2012)

She opens Red with one of her grandest love songs in arena-rock drag, and the U2 vibe makes sense since she’s also got a red guitar and the truth. If “State of Grace” is her U2 song, what’s the U2 song that sounds most like Taylor? Probably “All I Want Is You,” though you could make a strong case for “A Sort of Homecoming.”

Best line: “Up in your room and our slates are clean/Twin fire signs, four blue eyes.” Listen here.

Taylor Swift - Sparksfly

Rob Verhorst/Redferns/Getty Images

26

“Sparks Fly” (2010)

“Drop everything now! Meet me in the pouring rain!” Oh, this girl loves her precipitation scenes, but “Sparks Fly” really brings the thunder. It shows off her uncanny power to make a moment sound gauchely private and messily public at the same time. (Waxahatchee has another excellent song called “Sparks Fly” — no relation.)

Best line: “Just keep on keeping your eyes on me.” Listen here.

Taylor Swift - The Man

Kevin Winter/Getty Images

25

“The Man” (2019)

Imagine a timeline where Taylor released this as the first single from Reputation, instead of “Look What You Made Me Do.” It’s safe to say people might have gotten the message faster. “The Man” is the sharpest feminist anthem she’s written (so far). The unspoken subtext: If these dudes had to spend a day in her shoes, they’d crumble like a soggy chunk of feta cheese.

Best line: “When everyone believes you, what’s that like?” Listen here.

Taylor Swift - Begin Again
24

“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.

Taylor Swift - Fearless

Jason Kempin/Getty Images

23

“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 five times in a row, to the point where it’s one of history’s most curiously overlooked perfect pop albums. 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.

Best line: “You’re just so cool, run your hands through your hair / Absent-mindedly making me want you.” Listen here.

Taylor Swift - 22
22

“22” (2012)

Approximately 22,000 times more fun than actually being 22. The best song about turning the double deuce since Neil Young’s “Powderfinger,” if not the Stratford 4’s “Telephone,” it’s also her first shameless disco trip, with that Nile Rodgers-style guitar flash. But the power move is that “uh oh” into the chorus – the oldest trick in the book, except she makes it sound brand new every time.

Best line: “This place is too crowded, too many cool kids.” Listen here.

Taylor Swift - Last Kiss

Jeff Kravitz/FilmMagic/Gett Images

21

“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. One of those flawless Nathan Chapman productions – so sparse, so delicate, flattering every tremor of her voice.

Best line: “I’m not much for dancing, but for you I did.” Listen here.

Taylor Swift - Cornelia Street

Andrew H. Walker/Shutterstock

20

“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 haunted heartbreak hotel.

Best line: “Baby, I get mystified by how this city screams your name.” Listen here.

Taylor Swift - Ours
19

“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.

Our Song
18

“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.

Taylor Swift - Red

Amanda Schwab/Starpix/Shutterstock

17

“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.

Taylor Swift - New Years Day

Jun Sato/TAS18/Getty Images

16

“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.

Taylor Swift - Fifteen
15

“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.

Taylor Swift - Clean

Christopher Polk/Getty Images

14

“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.

Taylor Swift - Getaway Car

Jason Kempin/TAS18/Getty Images

13

“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 informs 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.

Taylor Swift - Enchanted

Larry Busacca/Getty Images

12

“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.

Taylor Swift - The Archer

Chelsea Lauren/Shutterstock

11

“The Archer” (2019)

For a few weeks last summer, this was the world’s favorite new Taylor song, until she dropped “Lover,” which stole all the thunder because it’s even better. So “The Archer” is underrated at this point. But it’s 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 absolute 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.

Taylor Swift - Holy Ground

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10

“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.

Taylor Swift - Dear John

Matt Sayles/AP/Shutterstock

9

“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.

Taylor Swift - We Are Never Getting Back Together
8

“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.

Taylor Swift - Blank Space
7

“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.

Taylor Swift - Long Live

Owen Sweeney/Shutterstock

6

“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.

Taylor Swift - Lover
5

“Lover” (2019)

Ladies and gentlemen, will you please stand? This mid-August bombshell is the kind of majestic 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.

 

Taylor Swift - Delicate
4

“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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