All Ranked by Rob Sheffield

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.”

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.”

Apprentice work from the debut, when she was still learning the ropes as a country songwriter. Yet, the seeds of greatness are already there. Historical significance: This was the song where Tay discovered rain imagery, which in her hands was the equivalent of Sir Isaac Newton inventing calculus.

Best line: “I’ll be strong/I’ll be wrong/Oh, but life goes on.”

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?”

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.”

A long, long, very long duet with former Good Charlotte and Fall Out Boy tourmates Boys Like Girls, who are either from London or Nashville (they seem to switch accents at random). For some reason, they decided to delay her entrance until a minute into the song, arguably the worst decision in the history of decisions.

Best line: “You already got me coming…undone.”

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.”

This one will be tough to explain to future generations, but here goes: So they made this Hollywood movie out of the Broadway musical Cats. Full of magic, furry, singing cats. So much fur. So much magic. Taylor plus felines — it should add up to classic cinema, right? Not quite.

Best line: “Macavity’s a mystery cat / He’s called the Hidden Paw.”

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.”

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.”

One of those beloved Taylor traditions: the Lead Single That Reveals Absolutely Nothing About the New Album. And for the second time in a row, it’s the weakest track by a mile. Honestly, Taylor would have released “Maxwell’s Silver Hammer” as the first single from Abbey damn Road. “ME!” is her only song title with an exclamation point, an oddity for this most !!! of singers. Even Brendon Urie sounds squeamish, and he’s the guy who once released a song called “Folkin’ Around.” As we now know, she had “Cruel Summer” in the can, but opted not to make it the summer jam of 2019 because she decided to release “ME!” instead, a decision that will be studied by Swiftian scholars for years to come.

Best line: “Hey kids, spelling is fun!”

Still a rookie, still learning, still trying to get away with “read between the lines” and “the road less traveled by” in the same verse.

Best line: “Nothing seems to work the first few times/Am I right?”

This track is 4 minutes and 24 seconds long, and involves 5 different cello players. The letters “K,” “I,” and “M” are capitalized in the title, a reminder that there’s an excellent new Kim Gordon album. Sisyphus must appreciate the shout-out, but he’d probably rather roll a boulder uphill for all eternity than hear another song about this feud.

Best line: “The blood was gushin’.”

An early country throwaway, released a decade later on Ingram’s From the Vault: Live 2007-2009. A teenage Swift chirps back-up harmony, doing the part originally sung by Sheryl Crow.

Best line: “Sign our names in the dust on your family car.”

She wrote this with Andrew Lloyd Webber for the Cats soundtrack — as she said, “If you can’t get T.S. Eliot, get T.S.”

Best line: “I watch from the dark, wait for my life to start / With no beauty in my memory.”

A perfunctory cheating-is-bad homily, with barely any chorus.

Best line: “I feel a responsibility/To do what’s upstanding and right.”

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.”

A warm-up for the synth-pop of 1989, from the One Chance soundtrack.

Best line: “What a sight when the light came on.”

A Lois Lane fantasy left off Speak Now, but it gets a real upgrade with her Taylor’s Version vocal muscle.

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

“I start a fight ’cause I need to feel something” – give her credit for honesty, even in this raw phase.

Best line: “Every smile you fake is so condescending.”

“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!”

“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?”

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.”

Neither she nor Zayn sound deeply interested in this dueling-falsettos battle from the Fifty Shades Darker soundtrack. Maybe it works in the movie, but who wants to go find out? Really, they sound like two ghosts standing in the place of…sorry, sore subject, let’s drop it.

Best line: “I’ve been looking sad in all the nicest places.”

A through-the-years romance, with a sweet homespun touch.

Best line: “I’ll be 87, you’ll be 89/I’ll still look at you like the stars that shine in the sky.”

A duet from McGraw’s album Two Lanes of Freedom, with a guitar solo from Keith Urban. The plot: His ex is driving away, listening to a Taylor song on the radio, as Tay tries to coax the woman into turning the car around and going home. Perhaps McGraw’s finest duet since his great lost Nelly jam, “Over and Over.”

Best line: “I bet you’re bending God’s ear talking ’bout me.”

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.”

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?”

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.”

A live acoustic tribute to the then-recently departed Michael Jackson, with a bit of Motown tremble in her voice.

Best line: “Oh darling, I was blind to let you go.”

“Only the Young” debuted in her excellent doc Miss Americana, a synth-pop tribute to the next generation of political activists. It’s also a clever Swiftian fake-out, giving everyone a totally wrong idea of where she was headed musically — almost like she was announcing, “Nothing to see here, folks. Definitely no keepers left over from the Lover era.” Was she already plotting to catch us off guard with Folklore? Don’t put it past her. But you’d never guess she was about to make an acoustic album full of folk songs about sweaters.

Best line: “Up there’s the finish line / Our future is worth the fight.”

A tale of romanticism gone sour, with a precocious child grown into an alienated introvert who escapes to “the secret garden in my mind.” The 1830s line isn’t even the real verbal groaner in this song—that would be “if comfort is a construct,” which wins this album’s The Kind Under Where a Tree Has Grown award. But since “I Hate It Here” connects to “The Lakes,” it’s worth noting the 1830s sucked for Wordsworth and Coleridge. 

Best line: “I’ll save all my romanticism for my inner life.”

A perky early throwaway about a teenage crush, recorded for her debut and briefly released as a bonus track.

Best line: “He loves to argue, born on the 17th.”

The Rihanna hit, briefly covered on the Live from SoHo digital album. Her finest Ri tribute remains her 2011 version of “Live Your Life” with T.I. onstage in Atlanta – sadly unreleased, but a duet that deserves to be enshrined for the ages.

Best line: “Stand under my umbrella, ella, ella.”

The reason fans once cared about rap beefs: they inspired great songs, whether it was Queens vs. the Bronx (“The Bridge” vs. “The Bridge Is Over” vs. “Have a Nice Day”) or LL Cool J vs. Kool Moe Dee (“How Ya Like Me Now” vs. “Jack the Ripper” vs. “Let’s Go” vs. “To Da Break of Dawn”). But this just sounds like a trivial time-waster by her standards – Swift’s celebrity feuds are not really one of the hundred most interesting things about her. The main attraction is the retro Panic! at the Disco vibe. “Look What You Made Me Do” turned out to be the lamest track on Reputation, but an impressively perverse head fake – a lead single that ended up having nothing to do with the album, musically or conceptually, making sure her new relationship songs would come as a surprise. To find a comparable stunt, you might have to go back to 1982, when Michael Jackson fooled the world into thinking Thriller was going to be a whole album of “The Girl Is Mine.”

Best line: “It’s much better to face these kinds of things with a sense of poise and rationality.” Oh wait – that actually is Panic! at the Disco.

“I wanna brainwash you into loving me forever / I wanna transport you to somewhere the culture’s clever”—for Tay, that means a fantasy of Gay Paree. But the whole point of this song is that you can make your own Paris wherever you are, just by drawing your own dream map on the bedroom ceiling. And if you have an amour to share the dream with, all the better. “All the outfits were terrible, 2003 unbearable”—sounds like Taylor found somebody’s Friendster photo stash of crop tops and trucker hats. “Did you see the photos? / No, I didn’t, but thanks though” is being kind. 

Best line: “Privacy sign on the door and on my page and on the whole world / Romance is not dead if you keep it just yours.”

If “Karma” is a cat, “CANCELLED!” is a squirle. She’s told this story countless times before, but almost always better, especially on The Tortured Poets Department, which makes you wonder if this is even a 2020s song or some still-unfinished Rep outtake. (“Did you girlboss too close to the sun,” whew.) The Nineties indie-rock guitar intro and Macbeth quote deserve a snazzier castle to call home.

Best line: “You know who your friends are / They’re the ones with matching scars.”

An Ed Sheeran ballad, refurbished into a sweet duet with his long-running favorite co-star. The video has the same actors who played Ed and Tay as little kids in the “Everything Has Changed” video — ten years later. Both singers sound right at home with the metaphor of a poker game — Ed can’t see it in her face, but she’s about to play her ace. 

Best line: “I’ve been played before, if you hadn’t guessed/So I kept my cards close to my foolproof vest.”

The Earth, Wind & Fire classic, already covered by every wedding band on the planet, becomes a mournful banjo lament. It’s her tribute to the late great Maurice White, a songwriter who shared her knack for building hits out of quirky details. (Changing “the 21st night of September” to the 28th is a very Swiftian touch.) Next she might try “That’s the Way of the World” or “After the Love Has Gone.”

Best line: “Love was changing the minds of pretenders.”

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

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

Future reaffirms her long-running bond with ATLien hip-hop, which goes back to her B.o.B. and T.I. duets. Plus her trusty wingman Ed Sheeran. She offers an update about her lipstick status (still red! good to know) and her relationship with drama: “I swear I don’t love the drama — it loves me!”

Best line: “I bury hatchets, but I keep maps of where I put ‘em.”

A Fearless outtake refurbished as a duet with her old friend Keith Urban. She pleads for forgiveness after crushing a lover’s heart for no particular reason, in the mode of “Back to December” or “Afterglow.”

Best line: “I knew my words were hard to hear/And harder to ever take back.”

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.”

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.”

One of her many, many songs set at 2 a.m. – clearly the most inspiring hour on Swift Standard Time – with a staccato disco guitar lick.

Best line: “We’re a crooked love in a straight line down.”

“This song is about a girl who had a dream and followed it,” Kenny Chesney tells the roaring Nashville crowd. One of those girls jumps onstage to sing along. “My friend Taylor Swift showed up on my birthday to surprise me,” Kenny explained. “In a lot of ways, that song and that lyric is Taylor’s journey.” Their touching “Big Star” duet came out on his concert album Live from No Shoes Nation — 10 years after he gave this rookie a break as the opening act on his 2007 summer tour. There is no loyalty like Swift loyalty.

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

“Before you, I’d 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.

Best line: “You came in wearing a football helmet and said, ‘Okay, let’s talk.’”

A catchy oddity that resembles Olivia Rodrigo’s “Get Him Back,” except Taylor does not meet this guy’s mom just to tell her her son sucks. 

Best line: “Once you fix your face, I’m going in.”

Some of the Speak Now vaulties sound like she’s already rehearsing for Red, but “Foolish One” feels totally Fearless. It’s a guileless country ballad about a girl learning to trust her instincts. Can you believe she went from this song to “Shake It Off” in four years? Talk about an upgrade in terms of Voices In My Head content. Love the way she wrote the hook “it’s delicate,” then decided to save that line until she could give it a song all its own. Like a lot of decisions she made in 2010, this was a prescient one.

Best line: “When my head is on your shoulder / It starts thinking you’ll come around.”

The first song Swift wrote with Max Martin and Shellback — the day she met them. It makes sense she left “Message in a Bottle” off Red, since it sounds so similar to “22”— she chose the right one. But it sounds like she’s already stretching ahead to 1989. “How is it in London?” sounds like a fresh take on the transatlantic rendezvous of “Come Back…Be Here.”

Best line: “I became hypnotized by freckles and bright eyes, tongue-tied.”