In this business, there are two subjects that will boost your page views like nothing else: Game of Thrones and Taylor Swift. One of them is a massive, multi-million-dollar enterprise filled with violence and betrayal, and the other aired on HBO. I find it hard to explain why exactly, and I’m sure Swift would, too: Somehow, this one 29-year-old woman from Wyomissing, Pennsylvania, keeps finding herself at the center of our national conversations about race, gender, celebrity, victimhood, even the economics of the tech industry. And, outside the legions of fans who eat up everything she puts out, no take on her ever stays solid for long. She was a precocious teenager, and the ultimate embodiment of white privilege. She’s been feminism’s worst nightmare, and an advocate for victims of sexual assault. Some people say she’s a goddess of the alt-right. Other people say she’s Jewish.
And yet, unlike Madonna or Bowie, Swift got through the first 11 years of her career without any major reinventions. (For 1989, she embraced feminism and threw away the last vestiges of her Nashville sound, but those were basically just aesthetic changes.) If the word on her has shifted since her debut, it’s because we’ve changed, not her. Swift — or at least the version of Swift on her albums — has remained largely the same person since her debut: a thin-skinned, bighearted obsessive, with a penchant for huge romantic moments. People don’t slowly ease into a relationship in her songs; they show up at each other’s doors late at night and they kiss in the rain. An unworthy suitor won’t just say something thoughtless; he’ll skip a birthday party or leave a teenage girl crying alone in a hotel room. Listen to her songs and you’ll ache at the resemblance to the most dramatic moments in your own private history. Listen to too many and you might ache again at the nagging feeling that those stories of yours have all been a bit uneventful and drab by comparison. What sort of real life can stand up against fantasies like these?
So, uh, I don’t recommend you listen to this list top to bottom.
But I do recommend sampling as many of these songs as you see fit. Even with the widespread critical embrace of poptimism — a development I suspect has as much to do with the economics of online media as it does with the shifting winds of taste — there are still those who see Swift as just another industry widget, a Miley or Katy with the tuner set to “girl with a guitar.” If this list does anything, I hope it convinces you that, underneath all the thinkpieces, exes, and feuds, she is one of our era’s great singer-songwriters. She may not have the raw vocal power of some of her competitors, but what she lacks in Mariah-level range she makes up for in versatility and personality. (A carpetbagger from the Pennsylvania suburbs, she became an expert code-switcher early in her career and never looked back.) And when it comes to writing instantly memorable pop songs, her only peers are a few anonymous Swedish guys, none of whom perform their own stuff. I count at least ten stone-cold classics in her discography. Others might see more. No matter how high your defenses, I guarantee you’ll find at least one that breaks them down.
Some ground rules: We’re ranking every Taylor Swift song that’s ever been released with her name on it — which means we must sadly leave out the unreleased 9/11 song “Didn’t They” as well as Nils Sjöberg’s “This Is What You Came For” — excluding tracks where Swift is merely “featured” (no one’s reading this list for B.o.B.’s “Both of Us”) but includinga few duets where she gets an “and” credit. Songwriting is an important part of Swift’s spellbook, so covers are treated more harshly than originals. Because Swift’s career began so young, we’re left in the awkward position of judging work done by a literal high-schooler, which can feel at times like punching down. I’ll try to make slight allowances for age, reserving the harshest criticism for the songs written when Swift was an adult millionaire.
*This post was originally published in November 2017. It has been updated to include Swift’s subsequent releases. Additionally, some rankings have changed to reflect the author’s evolving taste.
128. “Look What You Made Me Do,” Reputation (2017): “There’s a mistake that I see artists make when they’re on their fourth or fifth record, and they think innovation is more important than solid songwriting,” Swift told New York back in 2013. “The most terrible letdown as a listener for me is when I’m listening to a song and I see what they were trying to do.” To Swift’s credit, it took her six records to get to this point. On a conceptual level, the mission here is clear: After the Kim-Kanye feud made her the thinking person’s least-favorite pop star, this comeback single would be her grand heel turn. But the villain costume sits uneasily on Swift’s shoulders, and even worse, the songwriting just isn’t there. The verses are vacuous, the insults have no teeth, and just when the whole thing seems to be leading up to a gigantic redemptive chorus, suddenly pop! The air goes out of it and we’re left with a taunting Right Said Fred reference — the musical equivalent of pulling a Looney Tunes gag on the listener. Other Swift songs have clunkier rhymes, or worse production values, but none of them have such a gaping hole at the center. (I do dig the gleeful “Cuz she’s dead!” though.)
127. “Umbrella,” iTunes Live From Soho (2008): Swift has recorded plenty of covers in her career, and none are less essential than this 90-second rendition of the Rihanna hit recorded at the peak of the song’s popularity. It’s pure college-campus coffeehouse.
126. “Christmas Must Mean Something More,” The Taylor Swift Holiday Collection(2007): One of two originals on Swift’s early-career Christmas album, “Something More” is a plea to put the Christ back in Christmas. Or as she puts it: “What if happiness came in a cardboard box? / Then I think there is something we all forgot.” In the future, Swift would get better at holding onto some empathy when she was casting a critical eye at the silly things people care about; here, the vibe is judgmental in a way that will be familiar to anyone who’s ever reread their teenage diary.
125. “Better Than Revenge,” Speak Now (2010): A nasty little song that has not aged well. Whether a straightforward imitation of Avril Lavigne’s style or an early attempt at “Blank Space”–style self-satirization, the barbs never go beyond bratty. (As in “Look What You Made Me Do,” the revenge turns out to be the song itself, which feels hollow.) Best known now for the line about “the things she does on the mattress,” which I suspect has been cited in blog posts more times than the song itself has been listened to lately.
124. “American Girl,” Non-album digital single (2009): Why would you cover this song and make it slower?
123. “I Want You Back,” Speak Now World Tour – Live (2011): Another 90-second cover of a pop song that does not particularly benefit from a stripped-down arrangement.
122. “Santa Baby,” The Taylor Swift Holiday Collection (2007): Before Ariana Grande’s “Santa Tell Me,” there was only one holiday song about falling in love with Santa, and for some reason, we spent decades making all our young female singers cover it. Swift’s version leans out of the awkwardness by leaning into the materialism; she puts most of her vocal emphasis on the nice presents she hopes Santa will bring her. (The relationship seems to be fairly quid pro quo: She’ll believe in him if he gives her good gifts — even at this early stage, Swift possessed a savvy business sense.) Otherwise, this is a by-the-numbers holiday cover, complete with sleigh bells in the mix.
121. “Sweet Escape,” Speak Now World Tour – Live; Target edition DVD (2011): Swift’s sedate cover of the 2006 Gwen Stefani hit — those “ooh-ooh”s are pitched way down from Akon’s falsetto in the original — invests the song with a bittersweet vibe, though like anyone who’s ever tried the song at karaoke, she stumbles on the rapid-fire triplets in the first verse.
120. “Silent Night,” The Taylor Swift Holiday Collection (2007): Swift’s cover of the Christmas classic veers significantly away from Franz Xaver Gruber’s original melody, and even gives it a Big Taylor Swift Finale. Points for ambition, but sometimes you just want to hear the old standards the way you remember them.
119. “The Last Time,” Red (2012): Red is Swift’s strongest album, but it suffers a bit from pacing issues: The back half is full of interminable ballads that you’ve got to slog through to get to the end. Worst of all is this duet with po-faced Ulsterman Gary Lightbody, which feels about ten minutes long.
118. “Invisible,” Taylor Swift: Special Edition (2006): A bonus track from the debut that plays like a proto–”You Belong With Me.” The “show you” / “know you” rhymes mark this as an early effort.
117. “…Ready for It?,” Reputation (2017): The second straight misfire off the Reputation rollout, this one sees Swift try her hand at rapping, with some ill-advised bars about Elizabeth Taylor and a flow she borrowed from Jay-Z. (Try to rap “Younger than my exes” without spilling into “rest in peace, Bob Marley.”) Bumped up a spot or two for the chorus, a big Swift hook that sounds just like her best work — in this case, because it bites heavily from “Wildest Dreams.”
116. “I Heart ?,” Beautiful Eyes EP (2008): Swift code-switches like a champ on this charmingly shallow country song, which comes from the Walmart-exclusive EP she released between her first two albums. Her vocals get pretty rough in the chorus, but at least we’re left with the delightful line, “Wake up and smell the breakup.”
115. “Bad Blood,” 1989 (2014): When Swift teamed up with Max Martin and Shellback, the marriage of their dark eldritch songcraft nearly broke the pop charts. But when they misfire, the results can be brutal. The lyric here indulges the worst habits of late-period Swift — an eagerness to play the victim, a slight lack of resemblance to anything approaching real life — attached to a schoolyard-chant melody that will never leave your head, even when you may want it to. The remix hollows out the production and replaces Swift’s verses with two from Kendrick Lamar; it’s less embarrassing than the original, which does not make it more memorable.
114. “White Christmas,” The Taylor Swift Holiday Collection (2007): The most bluegrass of Swift’s Christmas tunes, this gentle rendition sees Swift’s vocals cede center stage to the mandolin and fiddle.
113. “Crazier,” Hannah Montana: The Movie soundtrack (2009): When approached by the filmmakers about contributing a song to the Hannah Montana movie, Swift sent in this track, seemingly a holdover from the Fearless sessions. In an admirable bit of dedication, she also showed up to play it in the film’s climax. It’s kind of a snooze on its own, but compared to the other songs on the soundtrack, even Swift’s leftovers shine.
112. “I’d Lie,” Taylor Swift (2006): A bonus track only available to people who bought Swift’s debut at Best Buy. It’s as cute as a study-hall MASH game, and just as easily disposable.
111. “Highway Don’t Care,” Tim McGraw’s Two Lanes of Freedom (2013): After joining Big Machine, McGraw gave Swift an “and” credit here as a professional courtesy. Though her backing vocals are very pleasant, this is 100 percent a Tim McGraw song.
110. “Superman,” Speak Now: Deluxe Edition (2010): A bonus track that’s not gonna make anyone forget Five for Fighting any time soon.
109. “Change,” Fearless (2008): A bit of paint-by-numbers inspiration that apparently did its job of spurring the 2008 U.S. Olympic team to greatness. They won 36 gold medals!
108. “Me!,” Lover (2019): Well, what did we expect? The run-up to “Me!” was preceded by a weeks-long guessing game about what precisely would be the nature of Swift’s big announcement on April 26, 2019. Would she come out? Would she come out and reveal she had once dated Karlie Kloss? Cut to the fateful day, and the news was … Swift, who is a pop singer, was releasing a new pop song. After the Sturm und Drang of the Reputation era, “Me!” is a return to anodyne sweetness, a mission statement that says, “I’m through making mission statements.” When it comes to reclaiming a sense of youthful innocence, the song is probably too successful — the we’re-all-just-kids-having-fun vibe aims for cheesy, and lands at grating.
107. “End Game,” Reputation (2017): Swift tries out her blaccent alongside Future and Ed Sheeran, on a track that sounds unmistakably like a Rihanna reject. The only silver lining? She’s better at rapping here than on “…Ready for It?”
106. “The Lucky One,” Red (2012): A plight-of-fame ballad from the back half of Red, with details that never rise above cliché and a melody that borrows from the one Swift cooked up for “Untouchable.”
105. “A Place in This World,” Taylor Swift (2006): Swift’s version of “Not a Girl, Not Yet a Woman,” this one feels like it missed its chance to be the theme tune for an ABC Family show.
104. “I Don’t Wanna Live Forever,” Fifty Shades Darker soundtrack (2017): In Fifty Shades Darker, this wan duet soundtracks a scene where Christian Grey and Anastasia Steele go for a sunny boat ride while wearing fabulous sweaters. On brand!
103. “Last Christmas,” The Taylor Swift Holiday Collection (2007): Swift does George Michael proud with this reverent cover of the Wham! classic.
102. “Breathless,” Hope for Haiti Now (2010): Swift covered this Better Than Ezra deep cut for the Hope for Haiti telethon. With only one take to get it right, she did not let the people of Haiti down.
101. “Bette Davis Eyes,” Speak Now World Tour – Live (2012): “There’s some unbelievable music that has come out of artists who are from L.A., did you know that?” Swift asks the audience at the beginning of this live track. The crowd, not being idiots, responds with an enthusiastic yes. This cover loses the two most famous parts of Kim Carnes’s original — the synths and Carnes’s throaty delivery — but the acoustic arrangement and Swift’s intimate vocals bring out the best qualities of the tune.
100. “Eyes Open,” The Hunger Games: Songs From District 12 and Beyond (2012): One of two songs Swift contributed to the first Hunger Games soundtrack. With guitars seemingly ripped straight out of 1998 alt-rock radio, this one’s most interesting now as a preview of Swift’s Red sound.
99. “Beautiful Eyes,” Beautiful Eyes EP (2008): The title track of Swift’s early-career EP finds the young songwriter getting a lot of mileage out of one single vowel sound: Besides the eyes of the title, we’ve got I, why, fly, cry, lullaby, even sometimes. A spirited vocal performance in the outro saves the song from feeling like homework.
98. “The Outside,” Taylor Swift (2006): If you thought you felt weird judging songs by a high-schooler, here’s one by an actual sixth-grader. “The Outside” was the second song Swift ever wrote, and though the lyrics edge into self-pity at times, this is still probably the best song written by a 12-year-old since Mozart’s “Symphony No. 7 in D Major.”
97. “SuperStar,” Fearless: Platinum Edition (2008): This bonus track is a relic of an unfamiliar time when Swift could conceivably be the less-famous person in a relationship.
96. “Starlight,” Red (2012): Never forget that one of the most critically acclaimed albums of 2012 contains a piece of Ethel Kennedy fanfiction. The real story of Bobby and Ethel has more rough spots than you’ll find in this resolutely rose-colored track, but that’s what happens when you spend a summer hanging in Hyannis Port.
95. “Sad Beautiful Tragic,” Red (2012): Another glacially paced song from the back half of Red that somehow pulls off rhyming “magic” with “tragic.”
94. “Innocent,” Speak Now (2010): The disparate reactions to Kanye West stage-crashing Swift at the 2009 VMAs speaks to the Rorschachian nature of Swift’s star image. Was Swift a teenage girl whose moment was ruined by an older man who couldn’t control himself? Or was she a white woman playing the victim to demonize an outspoken black man? Both are correct, which is why everyone’s spent so much time arguing about it. Unfortunately, Swift did herself no favors when she premiered “Innocent” at the next year’s VMAs, opening with footage of the incident, which couldn’t help but feel like she was milking it. (Fairly or not, the comparison to West’s own artistic response hardly earns any points in the song’s favor.) Stripped of all this context, “Innocent” is fine: Swift turns in a tender vocal performance, though the lyrics could stand to be less patronizing.
93. “Girl at Home,” Red: Deluxe Edition (2012): This Red bonus track offers a foreshadowing of Swift’s interest in sparkly ’80s-style production. A singsongy melody accompanies a largely forgettable lyric, except for one hilariously blunt line: “It would be a fine proposition … if I was a stupid girl.”
92. “A Perfectly Good Heart,” Taylor Swift: Special Edition (2006): A pleading breakup song with one killer turn of phrase and not much else.
91. “Mary’s Song (Oh My Oh My),” Taylor Swift (2006): This early track was inspired by Swift’s elderly neighbors. Like “Starlight,” it’s a young person’s vision of lifelong love, skipping straight from proposal to old age.
90. “Come in With the Rain,” Fearless: Platinum Edition (2008): An ode to a long-lost lover that follows the Swift template a tad too slavishly.
89. “Dancing With Our Hands Tied,” Reputation (2017): Reputation sags a bit in the middle, never more than on this forgettable ’80s-inspired track.
88. “Welcome to New York,” 1989 (2014): In retrospect, there could not have been a song more perfectly designed to tick off the authenticity police — didn’t Swift know that real New Yorkers stayed up till 3 a.m. doing drugs with Fabrizio Moretti in the bathroom of Mars Bar? I hope you’re sitting down when I tell you this, but it’s possible the initial response to a Taylor Swift song might have been a little reactionary. When it’s not taken as a mission statement, “Welcome to New York” is totally tolerable, a glimmering confetti throwaway with lovely synths.
87. “Tied Together With a Smile,” Taylor Swift (2006): When she was just a teenager with a development deal, Swift hooked up with veteran Nashville songwriter Liz Rose. The two would collaborate on much of Swift’s first two albums. “We wrote and figured out that it really worked. She figured out she could write Taylor Swift songs, and I wouldn’t get in the way,” Rose said later. “She’d say a line and I’d say, ‘What if we say it like this?’ It’s kind of like editing.” This early ballad about a friend with bulimia sees Swift and Rose experimenting with metaphor. Most of them work.
86. “King of My Heart,” Reputation (2017): Swift is fond of saying that “songs are what you think of on the drive home — you know, the Great Afterthought.” (She says it’s a Joni Mitchell quote, but I haven’t been able to find it.) Anyway, I think that’s why some of the love songs on Reputation don’t quite land: Swift is writing about a relationship from inside of it, instead of with hindsight. It’s a different skill, which could explain why the boyfriend character here is less vividly sketched than some of her other ones.
85. “Come Back … Be Here,” Red: Deluxe Edition (2012): A vulnerable track about long-distance love, with simple sentiments overwhelmed by extravagant production.
84. “Breathe,” Fearless (2008): A Colbie Caillat collaboration that’s remarkable mostly for being a rare Swift song about a friend breakup. It’s like if “Bad Blood” contained actual human emotions.
83. “Stay Beautiful,” Taylor Swift (2006): Nathan Chapman was a Nashville session guitarist before he started working with Swift. He produced her early demos, and she fought for him to sit behind the controls on her debut; the two would work together on every Swift album until 1989, when his role was largely taken over by Max Martin and Shellback. Here, he brings a sprightly arrangement to Swift’s ode to an achingly good-looking man.
82. “Nashville,” Speak Now World Tour – Live; Target edition DVD (2011): Swift gives some shine to singer-songwriter David Mead with a cover of his 2004 ballad. (Listen to the screams during the chorus and try to guess where this one was recorded.) She treats it with a delicate respect, like she’s handling her grandmother’s china.
81. “So It Goes,” Reputation (2017): Unfortunately not a Nick Lowe cover, this one comes and goes without making much of an impact, but if you don’t love that whispered “1-2-3,” I don’t know what to tell you.
79. “Drops of Jupiter,” Speak Now World Tour – Live (2012): The best of the covers on the live album sees Swift commit to the Train hit like she’d written it herself. If you had forgotten that this song came out in 2001, she keeps the line about Tae Bo.
78. “The Other Side of the Door,” Fearless: Platinum Edition (2008): A bonus track saved from mediocrity by a gutsy outro that hints that Swift, like any good millennial, was a big fan of “Semi-Charmed Life.”
77. “You Need to Calm Down,” Lover (2019): The song where Swift came out as an LGBTQ ally, and buried the hatchet with Katy Perry, all at the same time. The slangy Trump jabs (to say nothing of the slight West Indian accents in the chorus) may read as a few years behind the times, but when it comes to straight pop stars penning gay-rights theme songs, you could do a lot worse.
76. “Gorgeous,” Reputation (2017): In the misbegotten rollout for Reputation, “Gorgeous” righted the ship by not being completely terrible. Max Martin and Shellback pack the track with all sorts of amusing audio doodads, but the melody is a little too horizontal to stick, and the lyrics have a touch of first draft about them. (You’d be forgiven for preferring the actual first draft, which is slightly more open and real.)
75. “I Wish You Would,” 1989 (2014): Like “You Are in Love,” this one originated as a Jack Antonoff instrumental track, and the finished version retains his fingerprints. Perhaps too much — you get the sense it might work better as a Bleachers song.
74. “Cold As You,” Taylor Swift (2006): A dead-serious breakup song that proved the teenage Swift (with help from Rose, who’s got a co-writing credit) could produce barbs sharper than most adults: “You come away with a great little story / Of a mess of a dreamer with the nerve to adore you.” Jesus.
73. “Haunted,” Speak Now (2010): In which Swift tries her hand at Evanescence-style goth-rock. She almost pulls it off, but at this point in Swift’s career her voice wasn’t quite strong enough to give the unrestrained performance the song calls for.
72. “This Love,” 1989 (2014): Began life as a poem before evolving into an atmospheric 1989 deep cut. Like an imperfectly poached egg, it’s shapeless but still quite appetizing.
71. “Untouchable,” Fearless: Platinum Edition (2008): Technically a Luna Halo cover(don’t worry about it), though Swift discards everything but the bones of the original. Her subsequent renovation job is worthy of HGTV: It’s nearly impossible to believe this was ever not a Taylor Swift song.
70. “Wonderland,” 1989: Deluxe Edition (2014): A deranged bonus track that sees Swift doing the absolute most. This song has everything: Alice in Wonderland metaphors, Rihanna chants, a zigzag bridge that recalls “I Knew You Were Trouble,” screams. As she puts it, “It’s all fun and games ’til somebody loses their MIND!”
69. “Sweeter Than Fiction,” One Chance soundtrack (2013): Swift’s first collaboration with Jack Antonoff is appropriately ’80s-inspired, and so sugary that a well-placed key change in the chorus is the only thing that staves off a toothache.
68. “I’m Only Me When I’m With You,” Taylor Swift: Special Edition (2006): A rollicking pop-rock tune that recalls early Kelly Clarkson. As if to reassure nervous country fans, the fiddle goes absolutely nuts.
67. “Tell Me Why,” Fearless (2008): A bog-standard tale of an annoyingly clueless guy, but it’s paired with one of Swift and Rose’s most winning melodies.
66. “If This Was a Movie,” Speak Now: Deluxe Edition (2010): The mirror image of “White Horse,” which makes it feel oddly superfluous.
65. “How You Get the Girl,” 1989 (2014): The breeziest and least complicated of Swift’s guy-standing-on-a-doorstep songs, which contributed to the feeling that 1989 was something of an emotional regression. You probably shouldn’t take it as an instruction manual unless you’re Harry Styles.
64. “Don’t Blame Me,” Reputation (2017): A woozy if slightly anonymous love song that comes off as a sexier “Take Me to Church.” [A dozen Hozier fans storm out of the room.]
63. “The Way I Loved You,” Fearless (2008): Written in collaboration with Big and Rich’s John Rich, which may explain how stately and mid-tempo this one is. (There’s even a martial drumbeat.) Here, she’s faced with a choice between a too-perfect guy — he’s close to her mother and talks business with her father — and a tempestuous relationship full of “screaming and fighting and kissing in the rain,” and if you don’t know which one she prefers I suggest you listen to more Taylor Swift songs. Swift often plays guessing games about which parts of her songs are autobiographical, but this one is explicitly a fantasy.
62. “New Romantics,” 1989: Deluxe Edition (2014): Like “22,” an attempt at writing a big generational anthem. That it was left off the album proper suggests Swift didn’t think it quite got there, though it did its job of extending the singles cycle of 1989 a few more months. Despite what anyone says about “Welcome to New York,” the line here about waiting for “trains that just aren’t coming” indicates its writer has had at least one authentic New York experience.
61. “Sparks Fly,” Speak Now (2010): This one dates back to Swift’s high-school days, and was destined for obscurity until fans fell in love with the live version. After what seems like a lot of tinkering, it finally got a proper studio release on Swift’s third album. It’s like “True Love Waits,” but with more kissing in the rain.
60. “All You Had to Do Was Stay,” 1989 (2014): Just like the melody to “Yesterday” and the “Satisfaction” riff, the high-pitched “Stay!” here came to its writer in a dream. Inspiration works in mysterious ways.
59. “Stay Stay Stay,” Red (2012): Swift broke out her southern accent one last time for this attempt at homespun folk, which is marred by production that’s so clean it’s practically antiseptic. In an alternate universe where a less-ambitious Swift took a 9-to-5 job writing ad jingles, this one soundtracked a TV spot for the new AT&T family plan.
58. “Call It What You Want,” Reputation (2017): Many of the Reputation singles aim at sexy; this airy slow jam about losing yourself in love after a scandal is the only one that gets there, though the saltiness in the verses (“all the liars are calling me one”) occasionally betrays the sentiment.
57. “Ours,” Speak Now: Deluxe Edition (2010): It’s not this song’s fault that the extended version of Speak Now has songs called both “Mine” and “Ours,” and while “Ours” is good … well, it’s no “Mine.” Still, even if this song never rises above cuteness, it is incredibly cute. I think Dad’ll get over the tattoos.
56. “The Best Day,” Fearless (2008): Swift’s parents moved the family to Tennessee so she could follow her musical dreams, and she paid them back with this tender tribute. Mom gets the verses while Dad is relegated to the middle eight — even in song, the Mother’s Day–Father’s Day disparity holds up.
55. “Everything Has Changed,” Red (2012): “We good to go?” For many American listeners, this was the first introduction to a redheaded crooner named Ed Sheeran. It’s a sweet duet and Sheeran’s got a roughness that goes well with Swift’s cleaner vocals, but the harmonies are a bit bland.
54. “Today Was a Fairytale,” Valentine’s Day soundtrack (2010): How much of a roll was Swift on during the Fearless era? This song didn’t make the album, and sat in the vault for a year until Swift signed on for a small role in a Garry Marshall rom-com and offered it up for the soundtrack. Despite the extravagant title, the date described here is charmingly low-key: The dude wears a T-shirt, and his grand gestures are showing up on time and being nice.
53. “Last Kiss,” Speak Now (2010): A good-bye waltz with an understated arrangement that suits the starkness of the lyrics.
52. “You Are in Love,” 1989: Deluxe Edition (2014): The best of Swift’s songs idealizing someone else’s love story (see “Starlight” and “Mary’s Song”), this bonus track sketches Jack Antonoff and Lena Dunham’s relationship in flashes of moments. The production and vocals are appropriately restrained — sometimes, simplicity works.
51. “The Story of Us,” Speak Now (2010): The deluxe edition of Speak Now features both U.S. and international versions of some of the singles, which gives you a sense of how fine-tuned Swift’s operation was by this point. My ears can’t quite hear the difference between the two versions of this exuberant breakup jam, but I suspect the U.S. mix contains some sort of ultrasonic frequencies designed to … sorry, I’ve already said too much.
50. “Clean,” 1989 (2014): Co-written with Imogen Heap, who contributes backup vocals. This is 1989’s big end-of-album-catharsis song, and the water imagery of the lyrics goes well with the drip-drip-drip production. I’d be curious to hear a version where Heap sings lead; the minimalist sound might be better suited for her voice, which has a little more texture.
49. “I Almost Do,” Red (2012): The kind of plaintive breakup song Swift could write in her sleep at this point in her career, with standout guitar work and impressive vulnerability in both lyrics and performance.
48. “Long Live (We Will Be Remembered),” Speak Now (2010): Ostensibly written about Swift’s experiences touring with her band, but universal enough that it’s been taken as a graduation song by pretty much everyone else. Turns out, adolescent self-mythologizing is the same no matter where you are — no surprise that Swift could pull it off despite leaving school after sophomore year.
47. “This Is Why We Can’t Have Nice Things,” Reputation (2017): Put aside the title, which can’t help but remind me of the time Hillary Clinton tweeted “delete your account.”The same way “I Did Something Bad” is the best possible version of “Look What You Made Me Do,” this is a much better rewrite of “Bad Blood.” Swift brings back the school-yard voice in the chorus, but also so much more: She does exaggerated politeness in the bridge, she spins the “Runaway” toast, she says the words “Therein lies the issue” like she’s been listening to Hamilton. The high point comes when she contemplates forgiving a hater, then bursts into an incredulous guffaw. Reader, I laughed out loud.
46. “The Moment I Knew,” Red: Deluxe Edition (2012): An epic account of being stood up that makes a terrible birthday party seem like something approximating the Fall of Troy. If you’re the type of person who stays up at night remembering every inconsiderate thing you’ve ever done, the level of excruciating detail here is like a needle to the heart.
45. “Jump Then Fall,” Fearless: Platinum Edition (2006): An effervescent banjo-driven love song. I get a silly kick out of the gag in the chorus, when Swift’s voice leaps to the top of her register every time she says “jump.”
44. “Never Grow Up,” Speak Now (2010): Swift’s songs where she’s romanticizing childhood come off better than the ones where she’s romanticizing old age. (Possibly because she’s been a child before.) This one is so well-observed and wistful about the idea of children aging that you’d swear she was secretly a 39-year-old mom.
43. “Should’ve Said No,” Taylor Swift (2006): Written in a rush of emotion near the end of recording for the debut, what this early single lacks in nuance it makes up for in backbone. I appreciate the way the end of each verse holds out hope for the cheating ex — “given ooonnne chaaance, it was a moment of weeaaknesssss” — before the chorus slams the door in the dumb lunk’s face.
42. “Back to December,” Speak Now (2010): At the time, this one was billed as a big step for Swift: the first song where she’s the bad guy! Now that the novelty has worn off “Back to December” doesn’t feel so groundbreaking, but it does show her evolving sensitivity. The key to a good apology has always been sincerity, and whatever faults Swift may have, a lack of sincerity has never been one of them.
41. “The Archer,” Lover (2019): By 2019, Swift’s pattern with promotional releases was well-established: The first few singles are infectious bubblegum stuff, and not until those have become annoyingly inescapable do we get to hear the slower, more emotional material. As with “Gorgeous,” it’s tempting to grade “Archer” on a curve based on what came before, but I suspect this one will hold up. Jack Antonoff’s production now sounds as nostalgic for 2014 as it does 1989, but it never overwhelms the intriguing vulnerability of Swift’s lyrics. The line “I never grew up, it’s getting so old” is possibly the most self-aware lyric in the artist’s discography.
40. “Holy Ground,” Red (2012): This chugging rocker nails the feeling of reconnecting with an ex and romanticizing the times you shared, and it livens up the back half of Red a bit. Probably ranked too high, but this is my list and I’ll do what I want.
39. “Getaway Car,” Reputation (2017): Another very Antonoff-y track, but I’m not mad at it. We start with a vocoder she must have stolen from Imogen Heap and end with one of Swift’s most rocking outros, and in between we even get a rare key change and a “soary” that suggests the presence of at least one Canadian in the recording booth.
38. “Enchanted,” Speak Now (2010): Originally the title track for Swift’s third album until her label told her, more or less, to cut it with the fairy-tale stuff. It’s a glittery ode to a meet-cute that probably didn’t need to be six minutes long, but at least the extended length gives us extra time to soak up the heavenly coda, with its multi-tracked “Please don’t be in love in with someone else.”
37. “I Know Places,” 1989 (2014): No attempts of universality here — this trip-hop song about trying to find a place to make out when you’re a massive celebrity is only relatable to a couple dozen people. No matter. As a slice of gothic pop-star paranoia, it gives a much-needed bit of edge to 1989. Bumped up a couple of spots for the line about vultures, which I can only assume is a shout-out.
36. “Treacherous,” Red (2012): Swift has rarely been so tactile as on this intimate ballad, seemingly constructed entirely out of sighs.
35. “Speak Now,” Speak Now (2010): The rest of the band plays it so straight that it might take a second listen to realize that this song is, frankly, bonkers. First, Swift sneaks into a wedding to find a bridezilla, “wearing a gown shaped like a pastry,” snarling at the bridesmaids. Then it turns out she’s been uninvited — oops — so she decides to hide in the curtains. Finally, at a pivotal moment she stands up in front of everyone and protests the impending union. Luckily the guy is cool with it, so we get a happy ending! All this nonsense undercuts the admittedly charming chorus, but it’s hard not to smile at the unabashed silliness.
34. “22,” Red (2012): Another collaboration with Martin and Shellback, another absurdly catchy single. Still, there’s enough personality in the machine for this to still feel like a Taylor song, for better (“breakfast at midnight” being the epitome of adult freedom) and for worse (the obsession with “cool kids”). Mostly for better.
33. “Christmases When You Were Mine,” The Taylor Swift Holiday Collection (2007): The clear standout of Swift’s Christmas album, with an endearingly winsome riff and lyrics that paint a poignant picture of yuletide heartbreak. If you’ve ever been alone on Christmas, this is your song.
32. “Lover,” Lover (2019): She’s gone alt-country. The title track from Swift’s seventh album turned out to be a self-consciously muted ballad about slowing down and settling down into an adult relationship. With a vibe like that, who better to evoke than the patron saint of weary 30-somethings, Jenny Lewis? It’s trodding ground she’d already covered in “New Year’s Day,” but by this point in Swift’s career, I’d much rather hear her mine this vein than release an umpteenth singsongy single. The closing wedding waltz veers a little too far off track for me, but it’s rescued (somewhat) by an energetic performance.
31. “Dress,” Reputation (2017): An appropriately slinky track that gives us an unexpected payoff for years of lyrics about party dresses: “I only bought this dress so you could take it off,” she says in the chorus. The way the whole song starts and stops is an obvious trick, but I like it.
30. “White Horse,” Fearless (2008): You’d never call Swift a genre deconstructionist, but her best work digs deeper into romantic tropes than she gets credit for. In just her second album, she and Rose gave us this clear-eyed look at the emptiness of symbolic gestures, allegedly finished in a mere 45 minutes. Almost left off the album, but saved thanks to Shonda Rhimes.
29. “I Knew You Were Trouble,” Red (2012): The guiding principle on much of Redseems to have been to throw absolutely every idea a person could think of into a song and see what worked. Here, we go from Kelly Clarkson verses to a roller-coaster chorus to a dubstep breakdown that dates the song as surely as radiocarbon — then back again. It shouldn’t hang together, but the gutsy vocals and vivid lyrics keep the track from going off the rails.
28. “Teardrops on My Guitar,” Taylor Swift (2006): An evocative portrait of high-school heartbreak, equal parts mundane — no adult songwriter would have named the crush “Drew” — and melodramatic. It’s also the best example of Swift and Rose’s early songwriting cheat code, when they switch the words of the chorus around at the end of the song. “It just makes the listener feel like the writer and the artist care about the song,” Rose told Billboard. “That they’re like, “Okay, you’ve heard it, but wait a minute — ’cause I want you know that this really affected me, I’m gonna dig the knife in just a little bit deeper.’” (In a fitting twist, “Teardrops” ended up inspiring a moment that could have come straight out of a Taylor Swift song, when the real Drew showed up outside her house one night. “I hadn’t talked to him in two-and-a-half years,” she told the Washington Post. “He was like: ‘Hey, how’s it going?’ And I’m like: ‘Wow, you’re late? Good to see you?’”)
27. “Delicate,” Reputation (2017): With multitracked, breathy vocals, this is Swift at her most tentative. Would any other album’s Taylor be asking, “Is it cool that I said all that?” On an album where Swift attempted to play the villain without much success, the vulnerability plays better: This is the most genuinely sexy song on Reputation.
26. “Begin Again,” Red (2012): Swift’s sequencing genius strikes again: After the emotional roller coaster of Red, this gentle ballad plays like a cleansing shower. (It works so well she’d repeat the trick on 1989 and Reputation.) Of all Swift’s date songs, this one feels the most true to life; anyone who’s ever been on a good first date can recall the precise moment their nervousness melted into relief.
25. “Shake It Off,” 1989 (2014): Swift’s second No. 1 was greeted with widespread critical sighs: After the heights of Red, why was she serving up cotton-candy fluff about dancing your way past the haters? (Never mind that Red had its own sugary singles.) Now that we’ve all gotten some distance, the purpose of “Shake It Off” is clear: This is a wedding song, empty-headed fun designed to get both Grandma and Lil Jayden on the dance floor. Docked ten or so spots for the spoken-word bridge and cheerleader breakdown, which might be the worst 24 seconds of the entire album.
24. “Safe and Sound,” The Hunger Games: Songs From District 12 and Beyond(2012): Swift’s collaboration with folk duo the Civil Wars is her best soundtrack cut by a country mile. Freed from the constraints of her usual mode, her vocals paint in corners you didn’t think she could reach, especially when she tries out a high-pitched vibrato that blends beautifully with Joy Williams and John Paul White’s hushed harmonies. Swift has worked in a variety of emotional palettes in her career, but this is the only time she’s ever been spooky.
23. “Picture to Burn,” Taylor Swift (2006): Swift’s breakup songs rarely get more acidic than they do in this country hit. By the time she’s twanging a line about dating all her ex’s friends, things have gotten downright rowdy. The original lyrics — “Go and tell your friends that I’m obsessive and crazy / That’s fine, I’ll tell mine you’re gay” — show how far standards for acceptable speech in nice young people have shifted in the past decade.
22. “Fearless,” Fearless (2008): The title track from Swift’s second album has more of her favorite images — in one memorable twofer, she’s dancing in the rain while wearing her best dress — but she invests them with so much emotion that you’d swear she was using them for the first time. The exuberance of the lyrics is matched in the way she tumbles from line to line into the chorus.
21. “Tim McGraw,” Taylor Swift (2006): If you by chance ever happen to meet Taylor Swift, there is one thing you should know: Do not, under any circumstances, call her “calculating.” “Am I shooting from the hip?” she once asked GQ when confronted with the word. “Would any of this have happened if I was? … You can be accidentally successful for three or four years. Accidents happen. But careers take hard work.” However, since the title of her first single apparently came from label head Scott Borchetta — “I told Taylor, ‘They won’t immediately remember your name, they’ll say who’s this young girl with this song about Tim McGraw?’” — I think we’re allowed to break out the c-word: Calling it “Tim McGraw” was the first genius calculation in a career that would turn out to be full of them. Still, there would have been no getting anywhere with it if the song weren’t good. Even as a teenager, Swift was savvy enough to know that country fans love nothing more than listening to songs about listening to country music. And the very first line marks her as more of a skeptic than you might expect: “He said the way my blue eyes shined put those Georgia pines to shame that night / I said, ‘That’s a lie.’”
20. “I Did Something Bad,” Reputation (2017): It’s too bad Rihanna already has an album called Unapologetic, because that would have been a perfect title for Reputation, or maybe just this jubilant “Blank Space” sequel. Why the hell she didn’t release this one instead of “Look What You Made Me Do,” I’ll never know — not only does “Something Bad” sell the lack of remorse much better, it bangs harder than any other song on pop radio this summer except “Bodak Yellow.” Is that a raga chant? Are those fucking gunshots? Docked a spot or two for “They’re burning all the witches even if you aren’t one,” which doth protest too much, but bumped up just as much for Swift’s first on-the-record “shit.”
19. “Dear John,” Speak Now (2010): “I’ve never named names,” Swift once told GQ. “The fact that I’ve never confirmed who those songs are about makes me feel like there is still one card I’m holding.” That may technically be true, but she came pretty dang close with this seven-minute epic. (John Mayer said he felt “humiliated” by the song, after which Swift told Glamour it was “presumptuous” of him to think that the song his ex wrote, that used his first name, was about him.) She sings the hell out of it, but when it comes to songs where Swift systematically outlines all the ways in which an older male celebrity is an inadequate partner, I think I prefer “All Too Well,” which is less wallow-y. I’ve seen it speculated that the guitar noodling on this track is meant as a parody of Mayer’s own late-’00s output, which if true would be deliciously petty.
18. “Red,” Red (2012): Re-eh-eh-ed, re-eh-eh-ed. Red’s title track sees the album’s maximalist style in full effect — who in their right mind would put Auto-Tune and banjos on the same track? But somehow, the overstuffing works here; it’s the audio equivalent of the lyrics’ synesthesia.
17. “New Year’s Day,” Reputation (2017): Like a prestige cable drama, Swift likes to use her final track as a kind of quiet summing-up of all that’s come before. Here, she saves the album’s most convincing love song for last: “I want your midnights / but I’ll be cleaning up bottles with you on New Year’s Day” is a great way to describe a healthy relationship. The lovely back-and-forth vocals in the outro help boost this past the similar “Begin Again.”
16. “Forever & Always,” Fearless (2008): This blistering breakup song was the one that solidified Swift’s image as the pop star you dump at your own peril. (The boys in the debut were just Nashville randos; this one was about a Jonas Brother, back when that really meant something.) Obligatory fiddles aside, the original version is just about a perfect piece of pop-rock — dig how the guitars drop out at a pivotal moment — though the extended edition of Fearless also contains a piano version if you feel like having your guts ripped out. I have no idea what the lines about “rain in your bedroom” mean, but like the best lyrics, they make sense on an instinctual level. And to top it off, the track marks the introduction of Swift’s colloquial style — “Where is this GOoO-ING?” — that would serve her so well in the years to come.
15. “Mean,” Speak Now (2010): It takes some chutzpah to put a song complaining about mean people on the same album as “Better Than Revenge,” but lack of chutzpah has never been Swift’s problem. Get past that and you’ll find one of Swift’s most naturally appealing melodies and the joyful catharsis that comes with giving a bully what’s coming to them. (Some listeners have interpreted the “big enough so you can’t hit me” line to mean the song’s about abuse, but I’ve always read it as a figure of speech, as in “hit piece.”)
14. “Style,” 1989 (2014): The much-ballyhooed ’80s sound on 1989 often turned out to just mean Swift was using more synths than usual, but she nailed the vibe on this slinky single, which could have soundtracked a particularly romantic episode of Miami Vice. Despite the dress-up games in the chorus, this is one of the rare Swift love songs to feel truly adult: Both she and the guy have been down this road too many times to bullshit anymore. That road imagery is haunted by the prospect of death lurking around every hairpin turn — what’s sex without a little danger?
13. “Hey Stephen,” Fearless (2008): Who knew so many words rhymed with Stephen? They all come so naturally here. Swift is in the zone as a writer, performer, and producer on this winning deep cut, which gives us some wonderful sideways rhymes (“look like an angel” goes with “kiss you in the rain, so”), a trusty Hammond organ in the background, and a bunch of endearing little ad-libs, to say nothing of the kicker: “All those other girls, well they’re beautiful / But would they write a song for you?” For once, the mid-song laugh is entirely appropriate.
12. “Out of the Woods,” 1989 (2014): Like Max Martin, Antonoff’s influence as a collaborator has not been wholly positive: His penchant for big anthemic sounds can drown out the subtlety of Swift, and he’s been at the controls for some of her biggest misfires. But boy, does his Jack Antonoff thing work here, bringing a whole forest of drums to support Swift’s rapid-fire string of memories. The song’s bridge was apparently inspired by a snowmobile accident Swift was in with Harry Styles, an incident that never made the tabloids despite what seemed like round-the-clock coverage of the couple — a subtler reminder of the limits of media narratives than anything on Reputation.
11. “Wildest Dreams,” 1989 (2014): Swift is in full control of her instrument here, with so much yearning in her voice that you’d swear every breath was about to be her last. For a singer often slammed as being sexless, those sighs in the chorus tell us everything we need to know. Bumped up a few spots for the invigorating double-time bridge, the best on 1989.
10. “Love Story,” Fearless (2008): Full disclosure: This was the first Taylor Swift song I ever heard. (It was a freezing day in early 2009; I was buying shoes; basically, the situation was the total antithesis of anything that’s ever happened in a Taylor Swift song.) I didn’t like it at first. Who’s this girl singing about Romeo and Juliet, and doesn’t she know they die in the end? What I would soon learn was: not here they don’t, as Swift employs a key change so powerful it literally rewrites Shakespeare. The jury’s still out on the question of if she’s ever read the play, but she definitely hasn’t read The Scarlet Letter.
9. “State of Grace,” Red (2012): Swift’s songs are always full of interesting little nuggets you don’t notice until your 11th listen or so — a lyrical twist, maybe, or an unconventional drum fill — but most of them are fundamentally meant to be heard on the radio, which demands a certain type of songwriting and a certain type of sound. What a surprise it was, then, that Red opened with this big, expansive rock track, which sent dozens of Joshua Tree fans searching for their nearest pair of headphones. Another surprise: that she never tried to sound like this again. Having proven she could nail it on her first try, Swift set out to find other giants to slay.
8. “Ronan,” non-album digital single (2012): A collage of lines pulled from the blog of Maya Thompson, whose 3-year-old son had died of cancer, this charity single sees Swift turn herself into an effective conduit for the other woman’s grief. (Thompson gets a co-writing credit.) One of the most empathetic songs in Swift’s catalogue, as well as her most reliable tearjerker.
7. “We Are Never Ever Getting Back Together,” Red (2012): Flash back to 2012. Carly Rae Jepsen had a No. 1 hit. Freaking Gotye had a No. 1 hit. LMFAO had two. And yet Swift, arguably the biggest pop star in the country, had never had a No. 1 hit. (“You Belong With Me” and “Today Was a Fairytale” had both peaked at No. 2.) And so she called up Swedish pop cyborg Max Martin, the man who makes hits as regularly as you and I forget our car keys. The first song they wrote together is still their masterpiece, though it feels wrong to say that “We Are Never Ever Getting Back Together” was written; better to say that it was designed, as Swift and Martin turn almost every single second of the song’s 3:12 run time into a hook. Think of that guitar loop, the snippets of millennial-speak in the margins (“cuz like”), those spiraling “ooh”s, the spoken-word bit that could have been overheard at any brunch in America, and towering over it all, that gigantic “we.” Like all hyper-efficient products it feels like a visitor from some cold algorithmic future: The sense of joy here is so perfectly engineered that you get the sense it did not come entirely from human hands.
6. “Our Song,” Taylor Swift (2006): Swift wrote this one for her ninth-grade talent show, and I have a lovely time imagining all the other competitors getting the disappointment of their lives once they realized what they were up against. (“But nice job with that Green Day cover, Andy.”) Even at this early stage Swift had a knack for matching her biggest melodic hooks to sentences that would make them soar; that “’cause it’s late and your mama don’t know” is absolutely ecstatic. She’s said she heard the entire production in her head while writing, and on the record Nathan Chapman brings out all the tricks in the Nashville handbook, and even some that aren’t, like the compressed hip-hop drums in the final refrain.
5. “Mine,” Speak Now (2010): As catchy as her Max Martin songs, but with more of a soul, “Mine” wins a narrow victory over “Our Song” on account of having a better bridge. This one’s another fantasy, and you can kind of tell, but who cares — Paul McCartney didn’t really fall in love with a meter maid, either. Swift packs in so many captivating turns of phrase here, and she does it so naturally: It’s hard to believe no one else got to “you are the best thing that’s ever been mine” before her, and the line about “a careless man’s careful daughter” is so perfect that you instantly know everything about the guy. Let’s give a special shout-out to Nathan Chapman again: His backup vocals are the secret weapon of Speak Now, and they’re at their very best here.
4. “Blank Space,” 1989 (2014): You know how almost every other song that’s even a little bit like “Blank Space” ranks very low on this list? Yeah, that’s how hard a trick Swift pulls off on this 1989 single, which manages to satirize her man-eater image while also demonstrating exactly what makes that image so appealing. The gag takes a perfectly tuned barometer for tone: “Look What You Made Me Do” collapsed under the weight of its own self-obsession; “Better Than Revenge” didn’t quite get the right amount of humor in. But Swift’s long history of code-switching works wonders for her here, as she gives each line just the right spin — enough irony for us to get the jokes, enough sincerity that we’ll all sing along anyway. Martin and Shellback bring their usual bells and whistles, but they leave enough empty space in the mix for the words to ring out. Who wouldn’t want to write their name?
3. “Fifteen,” Fearless (2008): For many young people, the real experience of romance is the thinking about it, not the actual doing it. (For an increasing number, the thinking about it is all they’re doing.) Swift gets this almost instinctively, and never more than on this early ballad about her freshman year of high school, which plays like a gentle memoir. Listen to how the emotional high point of the second verse is not something that happens, but her reaction to it: “He’s got a car and you feel like flyyying.” She knows that the real thing is awkward, occasionally unpleasant, and almost guaranteed to disappoint you — the first sentence she wrote for this one was “Abigail gave everything she had to a boy who changed his mind / We both cried,” a line that became exhibit B in the case of Taylor Swift v. Feminism — and she knows how fantasies can sustain you when nothing else will. “In your life you’ll do things greater than dating the boy on the football team / but I didn’t know it at 15,” she sings, even though she’s only 18 herself. That there are plenty of people who spent their teenage years making out, smoking cigarettes, and reading Anaïs Nindoesn’t negate the fact that, for a lot of us squares, even the prospect of holding someone else’s hand could get us through an entire semester. Virgins need love songs, too.
2. “All Too Well,” Red (2012): It’s no wonder that music writers love this one: This is Swift at her most literary, with a string of impeccably observed details that could have come out of a New Yorker short story. “All Too Well” was the first song Swift wrote for Red; she hadn’t worked with Liz Rose since Fearless, but she called up her old collaborator to help her make sense of her jumble of memories from a relationship recently exploded. “She had a story and she wanted to say something specific. She had a lot of information,” Rose told Rolling Stone later. “I just let her go.” The original version featured something like eight verses; together the two women edited it down to a more manageable three, while still retaining its propulsive momentum. The finished song is a kaleidoscopic swirl of images — baby pictures at his parents’ house, “nights where you made me your own,” a scarf left in a drawer — always coming back to the insistence that these things happened, and they mattered: “I was there, I remember it all too well.” The words are so strong that the band mostly plays support; they don’t need anything flashier than a 4/4 thump and a big crescendo for each chorus. There are few moments on Red better than the one where Swift jumps into her upper register to deliver the knockout blow in the bridge. Just like the scarf, you can’t get rid of this song.
1. “You Belong With Me,” Fearless (2008): Swift was hanging out with a male friend one day when he took a call from his girlfriend. “He was completely on the defensive saying, ‘No, baby … I had to get off the phone really quickly … I tried to call you right back … Of course I love you. More than anything! Baby, I’m so sorry,’” she recalled. “She was just yelling at him! I felt so bad for him at that moment.” Out of that feeling, a classic was born. Swift had written great songs drawn from life before, but here she gave us a story of high school at its most archetypal: A sensitive underdog facing off with some prissy hot chick, in a battle to see which one of them really got a cute boy’s jokes. (Swift would play both women in the video; she had enough self-awareness to know that most outcasts are not tall, willowy blonde girls.) Rose says the song “just flowed out of” Swift, and you can feel that rush of inspiration in the way the lines bleed into each other, but there’s some subtle songcraft at work, too: Besides the lyrical switcheroos about who wears what, we also only get half the chorus the first go-round, just to save one more wallop for later. The line about short skirts and T-shirts will likely be mentioned in Swift’s obituary one day, and I think it’s key to the song’s, and by extension Swift’s, appeal: In my high school, even the most popular kids wore T-shirts.