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 115 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 to “…Ready for It?” – her latest offering. 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.
115. “Bad Blood” (2014)
Melodically parched, lyrically unfinished, rhythmically clunky – this was a mighty strange pick for a single from an album as loaded as 1989. There are a million things Taylor has in common with Paul McCartney – one is that celebrity grievances tend to sound like a penny-ante waste of their time, even when they’re totally understandable (unless you’re a fan of Macca’s “Dear Boy,” where John Lennon is his Katy Perry). The single remix is improved by Kendrick Lamar – but he wasn’t saving his A-game for this one.
Best line: “Band-Aids don’t fix bullet holes.”
114. “Santa Baby” (2007)
Yes, she made a Christmas album, which is full of contenders for the basement of this list. But an oldie about a gold digger wooing Little Saint Nick was perhaps a dubious pick for a singer still in her teens.
Best line: “I’ve been an awful good girl.”
113. “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/But life goes on.”
112. “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?”
111. “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.”
110. “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).
Best line: “You already got me coming…undone.”
109. “Out of the Woods” (2014)
Taylor loves to sing about boyfriends who are terrible drivers, but this guy takes the prize – he crashes her snowmobile and gets 20 stitches in the hospital. Call a cab, girl.
Best line: “Two paper airplanes flying, flying, flying.”
108. “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.”
107. “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.”
106. “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.”
105. “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 ever works the first few times/Am I right?”
104. “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.”
103. “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 write you a song/But I don’t wanna have to go that far.”
102. “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.”
101. “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 a hundred better ones.
Best line: “Me and my stupid pride, sitting here alone/Going through the photographs, staring at the phone.”
100. “Superman” (2010)
A Lois Lane fantasy, left off Speak Now for good reason.
Best line: “Tall dark and beautiful/He’s complicated, he’s so irrational.”
99. “Cold as You” (2006)
“I start a fight because I need to feel something” – give her credit for honesty, even in this raw phase.
Best line: “Oh, every smile you fake is so condescending.”
98. “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!”
97. “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.”
96. “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?”
95. “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.”
94. “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.”
93. “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 feeling sad in all the nicest places.”
92. “You Are in Love” (2014)
One of her through-the-years romances, this one featuring a snow globe.
Best line: “For once you let go of your fears and your ghosts.”
91. “Mary’s Song (Oh My My)” (2006)
Another through-the-years romance, but 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.”
90. “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 & Over.”
Best line: “I bet you’re bending God’s ear talking ’bout me.”
89. “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.”
88. “Nashville” (2010)
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?”
87. “The Sweet Escape” (2010)
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.”
86. “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 here is the retro Panic! at the Disco vibe. Here’s hoping it gets outshined by the rest of Reputation, the way “Shake It Off” was instantly eclipsed by the rest of 1989.
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.
85. “Stay Beautiful” (2006)
An early stab at a take-the-high-road breakup song.
Best line: “He whispers songs into my window.”
84. “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: “Now it’s much too late for me to take a second look.”
83. “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.”
82. “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.”
81. “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 were a crooked love in a straight line down.”
80. “Umbrella” (2008)
The Rihanna hit, briefly covered on the Live in 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.”
79. “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.”
78. “Breathe” (With 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.”
77. “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.”
76. “Untouchable” (2008)
A rare case where she retools somebody else’s song on one of her proper albums – the all-but-unknown Y2K-era rock band Luna Halo, who went on to open 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.”
75. “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?”
74. “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.”
73. “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!”
72. “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.”
71. “Jump Then Fall” (2008)
Ironclad rule of pop music: Songs about jumping are never a bad idea. Dig that “listens to Sublime once” vocal.
Best line: “I watch you talk, you didn’t notice.”
70. “Breathless” (2010)
Digging deep in the Nineties modern-rock crates, she does right by a previously obscure (to me) nugget from the New Orleans band Better Than Ezra – from 2005!, 10 years after their MTV hit! – as a charity benefit for the Hope for Haiti Now album.
Best line: “I’ll never judge you/I can only love you.”
69. “Superstar” (2008)
“You smile that beautiful smile, and all the girls in the front row scream your name.” No relation to the 1970s Leon Russell ballad immortalized by the Carpenters – except they’re both poignant ballads about groupies crushing on distant guitar boys. Well, as Journey warned, lovin’ a music man ain’t always what it’s supposed to be.
Best line: “You sing me to sleep every night from the radio.”
68. “Crazier” (2009)
Her ballad from Hannah Montana: The Movie, snagging her a cameo in the film. (But the highlight of the soundtrack will always be “Hoedown Throwdown.”) This is where Taylor and Miley crossed light sabers – although they’d meet again. Great title, too – even Taylor might probably admit Miley had her beat in this department, at least until the “Blank Space” video.
Best line: “Every sky was your own kind of blue.”
67. “Innocent” (2010)
Little-known fact: Did you know Kanye West once went onstage to interrupt Swift’s acceptance speech at the VMAs and threw a misogynist tantrum about how she didn’t deserve an award? Strange but true! “Innocent” was her song publicly forgiving him – seven freaking years ago – then they both released brilliant albums, and we all moved on with our lives. Dear Lord, if only this story had ended there.
Best line: “It’s okay/Life is a tough crowd.”
66. “Come Back…Be Here” (2012)
A yearning prayer for a rock & roll boy on tour, weak in the knees as she pleads for him to jet back on any terms he chooses.
Best line: “I guess you’re in London today.”
65. “Tied Together With a Smile” (2006)
An unsung highlight of the debut – a teen pep talk about self-esteem.
Best line: “Seems the only one who doesn’t see your beauty/Is the face in the mirror looking back at you.”
64. “Last Christmas” (2007)
Tay does the Wham! legacy proud – she should have also covered “Wake Me Up Before You Go-Go.” The ache and quaver of her voice fit the George Michael melancholy; this might be the saddest “Last Christmas” since the original. Plenty of us communed with this version last Christmas, the night we said goodbye to the guy who wrote it. R.I.P., George Michael.
Best line: “A girl on a cover, but you tore her apart.”
63. “Tell Me Why” (2008)
From Neil Young to the Beatles, “Tell Me Why” songs are tough to screw up, and even at 19, Tay’s too seasoned to let that happen.
Best line: “I need you like a heartbeat/But you know you got a mean streak.”
62. “Beautiful Eyes” (2008)
If you’re a fan of Swift’s Nineties modern-rock radio jones – one of her most fruitful long-running obsessions – check out this shameless tribute to the Cranberries. (But did she have to let it linger? Did she have to? Did she have to?)
Best line: “Baby, make me fly.”
61. “Everything Has Changed” (2012)
She and Ed Sheeran wrote this duet together in her backyard while bouncing on a trampoline, because of course they did.
Best line: “All I’ve seen since 18 hours ago is green eyes and freckles and your smile.”
60. “Love Story” (2008)
Romeo meets Juliet: proof that star-crossed teen romances never go out of style. She’s kept going back to the well of Shakespearean tragedy, quoting Julius Caesar in the “Look What You Made Me Do” video. It’s never been clear what the line “I was a scarlet letter” is doing in this song, but now it’s a hint that Tay was just a few years away from going full Hester Prynne in “New Romantics.”
Best line: “Just say yes.”
59. “Speak Now” (2010)
In real-life weddings, the preacher hardly ever invites the groom’s ex up to interrupt the ceremony. But if you’re a fan of Tay in stalker mode, this is priceless – crouching behind the curtains in the back of the church, waiting to pounce. “Horrified looks from everyone in the room” – you don’t say.
Best line: “It seems I was uninvited by your lovely bride-to-be.”
58. “Shake It Off” (2014)
A clever transitional single – great verses, grating chorus, pithy lyrics with a shout-out to her obvious inspiration, Robyn’s “Dancing on My Own.” As a lead single, “Shake It Off” might have seemed meager after 1989 came out – she was holding back “Blank Space” and “Style” and (Lord have mercy) “New Romantics” for this? But “Shake It Off” got the job done, serving as a trailer to announce her daring Eighties synth-pop makeover.
Best line: “It’s like I got this music in my head, saying it’s gonna be all right.”
57. “Better Than Revenge” (2010)
One of the basic rules of stardom is “never punch down” – don’t go after somebody one-thousandth as famous as you – but rules were made to be broken, and Taylor is the girl made to break them. Here, she goes Bruce Lee on a sexual rival who may or may not be the actress who had Alyssa Milano as her babysitter in the erotic thriller Poison Ivy 2. But as usual with Swift, her self-owns are the funniest part of the song.
Best line: “She thinks I’m psycho because I like to rhyme her name with things.”
56. “Welcome to New York” (2014)
People sure do love to complain about this song – in fact, the most authentically New York thing about it is how it sends people into spasms of mouth-foaming outrage. An explicitly queer-positive disco ode to arrivistes stepping out in the city that invented disco – “You can want who you want, boys and boys and girls and girls” – that will be bugging the crap out of you in rom-coms for years to come. (It made me throw a napkin at my in-flight screen during How to Be Single, when Dakota Johnson’s cab is going the wrong way on the Brooklyn Bridge – and I love this song.) Bumped up a few bonus notches for pissing everyone off, since that’s one of this girl’s superpowers.
Best line: “Searching for a sound we hadn’t heard before/And it said welcome to New York.”
55. “Drops of Jupiter” (2010)
I mistakenly thought this Train hit was deep-fried garbage until I heard Swift’s version and realized, “Hey, she’s right – this is the best soy latte I’ve ever had!” Props to Tay for bringing out the hidden greatness in this song – the stargazing lyrics and her voice go together like Mozart and tae bo. (The astrophysicist in my life would like me to point out that you can’t “make it to the Milky Way” because that’s the galaxy we already live in. In fact, you couldn’t leave the Milky Way if you tried. Science!)
Best line: “Tell me, did Venus blow your mind?”
54. “Haunted” (2010)
Enchanted to meet you, Goth Taylor. We’ll meet again.
Best line: “Something keeps me holding on to nothing.”
53. “Today Was a Fairy Tale” (2011)
Don’t let the title scare you away – it’s a plainspoken and genuinely touching play-by-play recap of a worthwhile date. In fact, “Today Was a Fairy Tale” and “If This Was a Movie” should trade titles, since this one feels realer and would make a better movie. It could rank higher, except she hugely improved it when she rewrote it as “Begin Again.” (Docked a couple notches for coming from the soundtrack of Valentine’s Day, which is the most dog-vomit flick Jessica Alba has ever made, and I say that as someone who paid money to see The Love Guru.)
Best line: “I wore a dress/You wore a dark gray T-shirt.”
52. “All You Had to Do Was Stay” (2014)
A 1989 banger that could have made an excellent single – it sounds a bit like “Out of the Woods,” except with a livelier chorus and a stormier range of electro-Tay sound effects.
Best line: “Let me remind you that this was what you wanted.”
51. “Eyes Open” (2012)
Finally, her long-overdue metal move, from The Hunger Games: Songs from District 12 and Beyond.
Best line: “Every lesson forms a new scar.”
50. “Treacherous” (2012)
“Put your lips next to mine/As long as they don’t touch” – now there’s an entrance line. Taylor braves the ski slopes of love, with a seething acoustic guitar that finally detonates halfway though.
Best line: “Nothing safe is worth the drive.”
49. “You Belong With Me” (2008)
One of her most pop-friendly early hits, singing in the role of a high school geek crushing on her best guy friend. When he comes out in college, they’ll have a few laughs about this. (And never let us forget the wisdom of Alicia Silverstone in Clueless: “Searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie.”
Best line: “She wears high heels, I wear sneakers/She’s cheer captain, and I’m on the bleachers.”
48. “I Almost Do” (2012)
A Red slow jam that could have worked even better sped up into a punked-out rocker – though it’s plenty affecting as is.
Best line: “Every time I don’t, I almost do.”
47. “…Ready for It?” (2017)
If by “it” you mean “literally any song that isn’t ‘Look What You Made Me Do,'” the answer is “extremely ready.” A major rebound from her previous release, a week earlier – the chorus of this one actually sounds like a Swift song, with a little air in the mix, giving the room she needs to pull off her intricate breathy effects. Max Martin knows how to shape a production around her voice. A hopeful omen for the rest of Repu TAY shun (hey, I just got that).
Best line: “You can be my jailor/Burton to my Taylor.”
46. “Stay Stay Stay” (2012)
“Before you, I only dated self-indulgent takers” – but here she turns into a self-indulgent taker herself and (surprise!) she likes it, a phone-throwing nightmare dressed like a grocery-shopping daydream. She finally meets a guy who can roll with her mood swings – even if she’s more in love with the mood swings than with the guy.
Best line: “You came in wearing a football helmet and said, ‘Okay, let’s talk.'”
45. “Safe and Sound” (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.”
44. “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.”
43. “You’re Not Sorry” (2008)
A dramatic piano-and-strings ballad from Fearless, showing off how much her voice has deepened between her first two albums.
Best line: “It’s taken me this long, baby, but I figured you out.”
42. “I Know Places” (2014)
She goes all Kate Bush, pursued across the moors by the hounds of love. This 1989 deep cut is underrated, but count on “I Know Places” to loom large in her canon over the years.
Best line: “My love, they are the hunters, we are the foxes.”
41. “Bette Davis Eyes” (2010)
Her kickiest left-field cover, from Speak Now Live. “I’d love to play you some music that I’m a fan of that’s come from L.A. – is that OK?” she asks the West Coast crowd, strumming her guitar. “This one came out in 1981 – eight years before I was born!” Virtually nobody seems to recognize it or sing along. Kim Carnes hit Number One with “Bette Davis Eyes,” but it was written by the great Jackie DeShannon, the only songwriter to collaborate with both Randy Newman and Jimmy Page. (Page wrote “Tangerine” for DeShannon!) The fact that Swift loves this classic ode to romantic espionage explains a lot.
Best line: “She’s pure as New York snow/She’s got Bette Davis eyes.”
40. “Wonderland” (2014)
Why did it take her five albums to get to Alice in Wonderland? Needless to say, Taylor Alison Swift fits right in on the other side of the looking glass, with white rabbits and Cheshire cats. Feed your head!
Best line: “It’s all fun and games till someone loses their mind.”
39. “The Lucky One” (2012)
She’s so lucky, she’s a star. For the record, T.S. did cover “Lucky” live once (and damn well, too), as a Britney tribute in Louisiana back in 2011.
Best line: “It’s big black cars and Riviera views/And your lover in the foyer doesn’t even know you.”
38. “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-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.”
37. “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.”
36. “Starlight” (2012)
“Oh my, what a marvelous tune” seems like a dauntingly quaint chorus, yet she makes it stick, in what sounds like an F. Scott Fitzgerald-themed whirlwind romance. That hook comes straight from the AC/DC playbook (specifically, the opening lines of “You Shook Me All Night Long”) – the sign of a truly sick pop scholar.
Best line: “We snuck into a yacht-club party/Pretending to be a duchess and a prince.”
35. “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: “Let me strike a match on all my wasted time.”
34. “Forever and Always” (2008)
She added this to Fearless at the last minute – just what the album needed. It’s a blast of high-energy JoBro-baiting aggro on her most anomalously shade-free album. “It rains in your bedroom” is a very on-brand Tay predicament.
Best line: “Did I say something too honest? Made you run and hide like a scared little boy?”
33. “Back to December” (2010)
One of the rare ballads where she goes crawling back to an ex she treated like dirt – and she’s surprisingly effective in the role. Although breaking into the guy’s house is a little extreme. (If she’s blocked by the chain on his door, that means she already picked the lock, right?) And sorry, but you’re seriously dreaming if you think I’m bothering to Google the name of that Twilight guy, don’t @ me.
Best line: “It turns out freedom ain’t nothing but missing you.”
32. “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.”
31. “The Story of Us” (2010)
You could credit this hit 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.”
30. “How You Get the Girl” (2014)
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 in the rain/She’ll open up the door and say ‘Are you insane?'”
29. “Hey Stephen” (2010)
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?”
28. “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.”
27. “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.”
26. “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?”
25. “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.”
24. “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.”
23. “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/And I will.”
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.”
21. “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.”
20. “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.”
19. “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 pines to shame that night/I said, ‘That’s a lie.'”
18. “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. (Yeah, OK, plus the one about the snowmobile.)
Best line: “You got that James Dean daydream look in your eye/And I got that red lip classic thing that you like.”
17. “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.”
16. “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. (The new Waxahatchee album has another excellent song called “Sparks Fly” – no relation.)
Best line: “Just keep on keeping your eyes on me.”
15. “Fifteen” (2008)
“In your life you’ll do bigger things than date the boy on the football team/I didn’t know that at 15.” Still south of her twenties, she sings her compassionately, sisterly yet hardass advice to her fellow teenage girls. (Spoiler: Boys are always lying about everything.)
Best line: “We both cried.”
14. “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.”
13. “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.”
12. “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 three 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 so cool, run your hands through your hair/Absent-mindedly making me want you.”
11. “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 at 2 a.m./Who do you love?”
10. “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 reeeeealslow/’Cause it’s late and your mama don’t know.”
9. “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 was like driving a new Maserati down a dead-end street.”
8. “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.”
7. “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.”
6. “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’re 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.”
5. “We Are Never 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: “I mean, I’m just like, this is exhausting, OK?
4. “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.”
3. “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 a point where it feels like it’s over and Tay’s bringing it in for a landing, except that’s when the song gets twice as good. 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.”
2. “New Romantics” (2014)
The way Taylor exhales at the end of the line “I’m about to play my ace-aaah” is perhaps the finest moment in the history of human lungs. “New Romantics” is where she takes the Eighties synth-pop concept of 1989 to the bank, with a mirror-ball epiphany that leaves tears of mascara all over the dance floor. She tips her cap to the arty poseurs of the 1980s New Romantic scene – Duran Duran, Adam Ant, the Human League, etc. – yet sounds exactly like her own preposterously emotional self. (One of my weirdest moments of recent years: explaining this song’s existence to the guys in Duran Duran.) “New Romantics” is hardly the first time she’s sung about crying in the bathroom, but it’s the one that makes crying in the bathroom sound like a bold spiritual quest, which (when she sings about it) it is. The punch line: Having written this work of genius, exceeding even the wildest hopes any fan could have dreamed, she left it off the damn album, a very New Romantic thing to do.
Best line: “We show off our different scarlet letters/Trust me, mine is better.”
1. “All Too Well” (2012)
So casually cruel in the name of being awesome. This towering ballad is Swift’s zenith, building to peak after peak. For “All Too Well,” she teams up with her trustiest collaborators – songwriting sensei Liz Rose, producer Nathan Chapman – to spin a tragic tale of doomed love and scarves and autumn leaves and maple lattes. It’s full of killer moments: the way she sings “refrigerator,” the way she spits out the consonants of “crumpled-up piece of paper,” the way she chews up three “all”s in a row. No other song does such a stellar job of showing off her ability to blow up a trivial little detail into a legendary heartache. (That scarf should be in the Rock and Roll Hall of Fame, though in a way it already is.) You can schaeden your freude all over the celebrity she reputedly sings about, but on the best day of your life you will never inspire a song as great as “All Too Well.” Or write one.
Best line: “Maybe we got lost in translation/Maybe I asked for too much/Maybe this thing was a masterpiece till you tore it all up/Running scared, I was there, I remember it all too well.”