Taylor Swift’s 75 Best Songs, Ranked

“You think I’m bulletproof, but I’m not” — now there’s a running theme, established in youth, that runs all the way through “I Can Do It With a Broken Heart.” The combination of indomitability and vulnerability never counts as an oxymoron in the Taylor Swift universe.

The funniest song title on “The Tortured Poets Department” (out of quite a few candidates!) has Swift using slang straight out of an old Warner Bros. gangster movie to describe the rush of freedom as she springs herself from one man’s jail to land in the liberation of another’s arms. At any given time on “Poets,” she seems to be describing different relationship situations, but this is the one time on the album she gives roughly equal weight to two different loves — the stultified one she’s running away and the old would-be flame she’s placing her first phone call to. Will the guy parked outside the penitentiary walls be as perfect as she remembers him? Well, that’ll be a subject for other songs, but everything sounds like a belated dream finally come true within the walls of this song. Unusually for a Swift song, this one dribbles out in a coda that seems nearly unattached to the rest of the song, setting up a “to be continued” feeling.

In case there was any doubt that it’s unresolved childhood loneliness and rejection that make the greatest breeding ground for uber-driven superstars, Swift clears it all up for us by effectively conceding as much here, in what amounts to childhood origin story for her ambition and independence. It’s somehow more affecting for how matter-of-factly she presents these subdued moments of almost steely self-realization. (Different people relate in different ways to a stark moment in their lives when they realized they may not have a parachute of personal relationships; Stevie Nicks has talked about how this number comforted her when she felt alone after Christine McVie died.)

A song about why a relationship that’s escalated for some of the wrong reasons can’t help but feel right when you throw that slinky a groove on it — and throw in something Swift has never employed from her arsenal before: a solo saxophone. When she pulled this out for an especially sexy-sounding second number on an “SNL” appearance, it made fans wish this was a direction she’d explore more in the future. Listen, she’s got time.

You’ll like her when she’s angry. There is nothing she does better than revenge, she told us as a youth, and that’s one thing that hasn’t changed with increased maturity since. Other recent songs of this ilk include the Kim Kardashian-themed song on the latest album. This one isn’t so clear in who it’s about, but it takes delight in the divorce of a wealthy nemesis, and suggests she had a hand in passing on the information that led to that split. Fiction? Maybe, but even as a fantasy, this expression of schadenfreude over a male enemy’s comeuppance feels close to her slightly blackened heart.

Every female singer with a little lung power and a big taste for drama should write their own version of a melodramatic Evanescence rock song at least once in their career. This heavily orchestrated Goth-rocker from her third album, “Speak Now,” came at the tail end of the era when she still had a touch of girlish shrillness in her voice. She is 100% — no, maybe 1000% — a better singer now than she was then, but that doesn’t mean we can’t feel a twinge of quaint nostalgia for the less trained, barely post-adolescent, I-mean-it tones pushing this anguished lament over the top.

This introductory, career-establishing single certainly counts as a simple pleasure now, against all the more sophisticated writing she’s done since. But its winsomeness still speaks to how we experience music as not just a soundtrack to life events but a spiritual partnership with them. The genius of it was in a concept that hadn’t been tried much before — establishing that a couple might not just have “our song” but “our artist.” And in making Tim McGraw the guy, thank God she chose someone whose name and stature have aged well. We wouldn’t have quite the nostalgic affection that we do for this 2006 single if the teen lovers had bonded over Big & Rich.

Swift has been surprisingly unafraid to boldly speak out about political matters in recent years, after being criticized for staying quiet in her early career. (Of course the blowback from going vocal has amounted to many times the crap she ever took for keeping her mouth shut.) She still hasn’t gotten topical too often in song itself, but a major exception came in the form of “Miss Americana and the Heartbreak Prince,” which subsequently lent half its name to a documentary about her political coming-out. This “Lover” track is basically a play on the idea that all adult life is just like high school, but now she’s breaking up not with a boy but with the center-right assumptions that had her growing up assuming that America would always stay on the right track. As tends to be the case with lyrics that exist entirely on a metaphorical plane, this isn’t one of her most emotionally connecting tracks. But to hear America’s one-time princess worry that she and the direction of her country may never, ever get back together is affecting.

When Swift revealed that she’d enlisted the Chicks for a collaboration, nearly everyone assumed it’d be a fun lark, like the murder ballad she eventually did with Haim. Instead, she murdered everyone’s hearts with “Soon You’ll Get Better,” a song about coming to terms with her mother’s cancer that hit upon many of the stages of grieving… not a death, but an illness that ends the carefree life a family once knew. This was most people’s “skip” track on the “Lover” album — not because it’s a weak song, but because it’s too powerful in prompting emotions to be played as regularly as a “Cruel Summer,” where the stakes aren’t so high. Even if you’re blessed not to currently have any loved ones with chronic or incurable illnesses, this is one to pull out only at cathartic intervals.

We knew they were trouble, good trouble, when they walked in — Max Martin and Shellback that is, who were charged with updating Swift’s sound for ja handful of tracks on her fourth album, “Red.” Nathan Chapman was still the bigger part of the production picture, doing his part in expertly helming sensitive, wounded classics-to-be like “All Too Well” and “Sad Beautiful Tragic.” But the introduction of the Swedish overlords was a sign that we weren’t in Kansas anymore, or anywhere else where country music is going to rule forever. “I Knew You Were Trouble” was the most radical of the steps forward, throwing something like actual dubstep into the mix for an artist who might have safely stuck with dobros. It’s slightly dated but still holds up. There’s almost a kind of musical violence to the electronic chorus, a jolting soundtrack for a woman throwing herself onto the tile over a bad call with a good looker.

Swift really, really likes women who are viewed as insane. Hard to imagine why, after a few solid years of vilification in the previous decade, right? And so, after she bought a Rhode Island mansion in the mid-2010s, she formed an identification with a famous former owner, wealthy socialite Rebekah Harkness, and decided to tell her story of how she became willfully self-ostracized from her community. There’s a theme running there between that tracks like “Mad Woman,” but also with the older Swift song “The Lucky One,” a portrait of a star who threw it all away and went into happy seclusion. This is a terrific piece of character writing, and though it’s hardly diaristic in the manner of so many other Swift songs, it is possibly telling us that what she aspires to become late in life is a “crazy,” rich and powerful old spinster lady trading dirty looks and derogatory laughs across the fence with the townspeople.

Happily married or coupled fans may consider this a skip on “Poets.” But on behalf of those who are’t, Swift poses the question: What if your soulmate is… a state of aloneness? Caught in the wake of a breakup after a relationship that seemed like the one, the singer ponders whether never being mated for life is so fated that it’s actually been written in the stars. The only leavening factor to this heartbreaker is that she at least imagines there might be a celestial appeals court.

No haters here, when it comes to this inspirational anthem, equally suitable for self-pep-talks in the bathroom mirror or to be played at ballgames.

In which Taylor Swift imagines her own demise. Well, not exactly, but in the tradition of the Eagles’ “New Kid in Town,” the singer is anticipating a time when she will be last year’s It Girl and no longer the current rage. (See also the latest album’s “Clara Bow.”) By the time she finally recorded this as a Vault track, it was clear that this would not need to be a going anxiety for her. But in any case, there was some cheek — and some chic — in how she chose the coolest lady of the moment, Phoebe Bridgers, someone whose indie records are much cooler than hers in some universe, to be her shadow on the new recording. Their voices sound so good together, they need to find a reason to reconvene.

Listening to “Tim McGraw” or “Teardrops” back in the day, how little would anyone have imagined that Swift someday would be decrying “the 1950s shit they want from me” while extolling the sensual benefits of a relationship that just cozily is what it is? “Lavender Haze” kicks off “Midnights” with a groove that’s almost a little too laid back to quite call R&B… although you could probably say that of a lot of the best subtle R&B. It’s Swift locked into a good groove in every possible regard.

For the huge weight this carries in the Swift catalog, this is one of the more divisive songs among card-carrying Swifties, with some fans holding some bad blood against the tune itself. (Fellow Swift-loving critic Rob Sheffield places this track dead-last, always, when he updates his rankings of every song she’s ever released.) Maybe they don’t like the fact that it is both grandiose and sing-songy, and that it makes something epic out of a grudge over a fight over touring musicians. (If you believe the old hype.) But if you can forget the song’s supposed origin story, and overlook how maybe the production sounds too big for its own good, and maybe focus in on the vulnerability of the bridge… “Bad Blood” is good. Who hasn’t experienced that moment where the “fren” part finally just gets cut out of “frenemies,” and needed an adult nursery rhyme to turn that frustration into a sing-along? This message brought to you by the Bad Blood Defense League.

Who has influenced who more — Swift, possibly affecting Lana Del Rey’s confessionalism from the start, or LDR, providing some guidance for Swift’s recent turns toward the languid? It’s a question that can easily be set aside to just enjoy the confluence of forces that is “weird but fucking beautiful” and that is “Snow on the Beach.” There is something almost comical about how Swift responded to fan outcries over the first version and gave the people what they wanted with a “More Lana Del Rey” remix in which her duet partner’s vocal finally got turned into a lead. Yes, more of any and all of this.

Before Swift name-checked herself in full in the last verse of the recent “Clara Bow,” she gave herself a “Taylor can’t come to the phone right now” moment in the first teaser track for “Reputation,” and Swifties were all dead. This song didn’t sit well with every fan — some considered it a little too hip-hoppy, just because of the spoken-word chorus. But for many of us, it holds up just fine, from the almost cinematically suspenseful pre-chorus to the droll delivery of the buck-passing title phrase. And that’s because it takes Swift’s admitted depression over the backlash she received after the Kanye/Kim experience (since rectified, in full) and makes something fun out of that despondence.

I’ve always thought of this, rightly or strangely, as Swift’s Peggy Lee song… her “Fever.” It still stands as one of the sultriest things she’s ever done: Look what he made her do.

Swift takes a backstage introduction to an indie-pop dude she had a crush on and turns it into something that feels like an epic moment at a royal ball. Even if you are a less than A-level romantic, you may still find something enduringly swoony about the way she frames something that feels like classic love at first sight (even if in practicality it’s check-his-socials-later-to-see-if-he’s-claimed at first sight). She probably forgot about the guy the next day, but she got a hell of a testament to the magic of instantaneous infatuation out of it. (And a fragrance.)

As the closing track on the 2019 “Lover” album, “Daylight” didn’t make that much of an impression; it seemed like maybe just one in a series of hopeful denouements to otherwise more dramatic collections, in a tradition with “New Year’s Day” and “Clean” but not as memorable. But the song turned out to be slightly the victim of a rare instance of overly busy balladic production that didn’t do the tune many favors. Stripped of that for a mostly acoustic version that appeared on a live album just before the pandemic, her of-the-moment love song became something more touching, like her one-night-only “Lover” show in the City of Lights really did bring it into the sunshine.

It’s easy to see a lot of the darker material on “Folklore” through two lenses — that they’re breakup songs, or they’re breakup-with-Big-Machine songs. Either interpretation of “Mad Woman” works, but if this is one of her personal tunes on the album and not one of the character songs, the unusual intensity with which she writes and sings it sure makes it seem like it’s more about a recent business split than some long-ago bad romance she’s dredging up for song fodder. Of course, this interpretation is furthered by just how openly angry she allowed herself to be in her public messages about what went wrong, to the extent she has to know some observers were asking, “Why can’t she just move on?” However you feel about the situation with the sale of the masters, you have to take note of her refusal to take it any less seriously over time. “Every time you call me crazy, it makes me more crazy,” she warns. A scorpion fighting back “strike(s) to kill, and you know I will.” Geez, we’re a long way from slamming screen doors and first or last kisses here — and it’s riveting.

Swift has had enough sensual songs on her albums in the last 10 years that it’s almost difficult to recall how mildly shocking it was to hear America’s sweetheart singing about being “tangled up with you all night, burning it down.” What’s most striking about the number, though, now and then, is the Planned Obsolescence theme of the lyrics, where Swift is singing about hot nights but also anticipating a cooled-off future in which her lover will regret no longer being with her. Most listeners probably ignored the future-sadness part and just rocked with the dreamy reverie.

This is the one that began it all, not on the country side of things, where she was already well-established before her sophomore album came out, but on the MTV side, where many “pop mixes” were to come before she finally “picked a lane,” as she put it. It sounds almost primitive now, but an honestly felt teardrop on an honest instrument never goes out of style. (Many years later, on “My Tears Ricochet,” she would subtly do a kind of sequel to this ballad, with record company executives understood to be replacing the far more benign Drew as the villains of the piece.)

The greatest of all of Swift’s blatantly autobiographical and adoring love songs — admittedly a small subset of her overall work, given her penchant for drama, but there is some strong competition there. Not always one to look for the supernatural in things, Swift does use this exquisitely plucked acoustic track to wonder if there might be some serendipity in the air, tying things together with a divine smile. The lyrics here felt so baldly true to life that you knew even before you Googled it that her significant other of many years will turn out to have toiled in a blue shirt in a yogurt shop, or that one of her celebrity exes did in fact have a newborn infant that would have precipitated a gift from her. So much specificity for one sweet ditty, but again, with a chorus easily adapted by any young lovers who also see their paths as intwined by something spookier than chance. This is no longer a song that she wants to perform live, for reasons that are apparent to anyone following her real-life story, now that she’s probably decided the situation described was more chance than cosmology. But it doesn’t have to stop being your song,

So many of Swift’s best post-breakup songs, especially in the early parts of her songwriting career, are her just reiterating the obvious to her exes, post-mortem. Like: All you had to do was… stay! All you had to say was… no! Dudes: You had one job.

The premise of the closing song of “Midnights” sounds almost megalomaniacal, when you read it on paper, and maybe even when you’re first hearing the brashness of the lyric. Swift sings that, as a not-so-evil genius, she pre-engineered every aspect of coming together with the partner with whom she now shares a deep, fulfilling relationship. It’s a statement of near-omnipotence you usually only find in pop songs with darker leanings. To an extent, we have to understand that she’s exaggerating, for effect, about these apparent superpowers of hers. And yet the end intent of the song is deeply serious: She’s explaining that women historically have to go to extreme lengths to be the steerer in relationships that controlling men typically screw up. There’s also a whole backstory about the childhood slights that led her to develop these powers to manipulate for good. This leads to one of the greatest lines in all of Swift-dom: “I swear, I’m only cryptic and Machiavellian ’cause I care.” Was she being tongue-in-cheek with that lyric? At least a little. Was she dead-serious, too? Undoubtedly.

A dire but weirdly satisfying fantasy of disruption. On the “Lover” album, with “Paper Rings,” Swift had also engaged — so to speak — in an engagement-ring scenario, but there, it was a joyful exploration of what it would feel like to make promises like paupers who couldn’t afford real rings. This song is the opposite in every conceivable way: The protagonist in her song says no to a proposal that was meant to lead to a big public pronouncement her would-be fiance had already promised his well-to-do family. Ruining everything is terrible and great and terrible again, as the singer imagines everyone saying, “She would’ve made such a lovely bride / What a shame she’s fucked in the head.” Once she would have played this for high musical melodrama, if she’d even have ventured to write a song so much not about herself before. Here, it’s all brilliant detail and delicacy on the way to that effed-up-ever-after ending.

This reads like one of the many works of fiction that Swift embarked upon with the “Folklore” album. At least, it’s hard to imagine that, even if she wanted to, a superstar is probably able to have the guilt-wracked “clandestine meetings” described in this deep dive into the morality and petty details of adultery. Yet Swift sure must have done some research with friends — or just has that vivid a literary imagination — to come up with absorbing details like “Leave the perfume on the shelf
that you picked out just for him / So you leave no trace behind” and “Tell your friends you’re out for a run / You’ll be flushed when you return.” Like, damn, girl. But this brilliantly written song isn’t just a list of 50 ways to meet your lover. There’s a real sense of panic, desire and self-loathing in verses describing an affair as “a dwindling, mercurial high — a drug that only worked the first few hundred times” and despairing: “You taught me a secret language I can’t speak with anyone else.” In just a few minutes, Swift has written a whole movie’s worth of insight about cheating. It certainly ought to give you faith in what she could pull off as an actual screenwriter.

With Swift in her 30s, it’s a long stretch back to remember a time in her life when teen girls had to look out for each other’s virtue, and cry over losing virginity to a loser. But in many ways, 15 — the song, and the age — is forever.

Swift hasn’t indulged much in actual country in recent years, so to hear her return to it in a Vault track with Stapleton in tow — and with some real swing to the track — was a big kick. The rootiser music is apropos to a highly playful lyric that has Swift playing the rube girlfriend — or ex-girlfriend — to a high-class beau who was to the manor born. Presumably this is a very belated Jake song… let’s not beat around the bush about that… and if so, we have him to thank for the chance to get Swift’s own version of “Friends in Low Places.”

Another of her “I asked just one thing of you: to not leave” songs. Having forbidden that one command, like Adam of the garden, he of course banished when he realized his mistake, too late. This could have been a much more conventional song, melodically. But Swift had a dream where all she could utter was the word “stay!,” in an unnaturally high voice — and she worked that effect into the chorus instead of keeping the vocal in a natural register. it’s just another example of a Swift move that feels risky when you first hear it within a song and seems perfectly natural, even inevitable by the third listen. As fun a trick as that is, I’m still struck most of all by the ballsiness of the song… that however desperately she wanted the relationship to continue, once a fellow calls it, there are no takebacks. (That happens a lot in the Swift ouevre.) That’s actually some pretty good role-modeling going on, for her still emotionally impressionable younger fans.

Swift’s most outright feminist statement could read as polemical, and maybe it counts. But agitprop doesn’t get too much more fun, or too much more indisputably true. “When everyone believes ya —
what’s that like?” asks the woman whose word was automatically assumed to be suspect, as opposed to that of a guy who subsequently proved to be the least reliable narrator the entertainment world has ever seen. But we digress. This one is really an I’m-every-woman anthem, not personal memoir, and she serves her gender well with one you-know-it’s-fact zinger after another. There’s hardly any line she’s ever written that has better wordplay than one of the simplest lines she’s ever written: “If I was a man, then I’d be the man.”

How many stitches did he get, Taylor? Twenty, was it? One reason her more autobiographical songs hold such power is her constant inclination to provide small details — eye color, necklace shapes, astrological signs, clothing items street names or, yes, numbers of stitches — while leaving fans to do guesswork, be it educated or fanciful, over just what kind of bigger picture these brushstrokes enhance. With “Out of the Woods,” one of the most talked-about tracks from “1989,” it’s really enough to know what the emotional tenor of the scenario is, and not who she spent a night in the emergency room with. If you can set some of those precise details on the back burner, you can experience it as a song about a relationship that’s come to some sort of reasonable plateau but isn’t really out of the woods yet. The telling way in the choruses that she keeps answering “good!” to every repetition of the “Are we in the clear yet?” question lets you know that this is a protagonist who constantly has to talk herself into believing that everything’s fine. The snowmobile emerged but she’s spending the whole lyric back in the trees.

If your tear ducts can withstand this bold line of attack from a song about Swift’s late grandmother, you’re made of more stoic stuff than most of the rest of us. For me, it was the receipts that finally got me — that is, the part where she’s singing, “I should’ve asked you how to be / Asked you to write it down for me / Should’ve kept every grocery store receipt / ‘Cause every scrap of you would be taken from me.” Any kid who ever took for granted that a cherished elder would always be around has been there, but the specificity of just how tiny a remnant she’d settle for is heart-rending. And it’s hard to imagine anything to melt your already-rended heart more than Swift pulling out the stops to actually include an audio excerpt of her grandmother’s operatic singing for a ghostly coda. This has been your pool (as in, puddle on the floor) reporter.

Swift has never sounded so exhausted as she does on this track… which is part of its novel appeal, and sense of a different kind of honesty, since tiredness is not her natural state. Normally, “depleted-sounding” would not be the highest compliment we could pay a song, but this one is different. It’s the sound of someone standing in a doorway, maybe for the rest of time, asking for one more chance with a last bit of willpower they can’t quite physically manifest. As down-tempo as it is, it’s also kind of an anthem of hope… and, in its anti-assuming fashion, a total, flat-out earworm.

This early triumph is what any of the hardboiled characters in “Folklore” or “Tortured Poets” department would understand as pure teen hokum… and if she ever drops it from her set, even when she’s 60, there might be riots in the streets. Justifiably. Any points lost for rewriting “Romeo and Juliet” to have a happy ending are immediately regained — with a thousand bonus points besides — for that key change. If Shakespeare could have had this on while he was writing, he might never have given a teenage heroine a moment’s sorrow again.

Yes, we are, or were, as a matter of fact. This “Reputation” opener made for a great introductory number on the 2018 tour of the same name, too. It gets knocked, in some quarters, for Swift having sung the verses in a kind of hip-hop cadence. But that does set up the constantly changing dynamics of the tune, which goes from that into a featherweight-sweet and sexy pre-chorus, before Max Martin and Shellback bring the hammer down again with a recurring synth riff that feels like heavy metal. That cathartic rush is worth the wait of the ellipses.

While it lasted, the career-reshaping teaming of Swift with co-writer/producers Max Martin and Shellback fell into the can-do-no-wrong category. The peak of their collaboration in terms of sheer ear candy might have been a number that for whatever reason got delegated to “1989” deluxe bonus track: “New Romantics.” That moment when the backing instrumental drops out and all we hear is Swift’s multi-tracked “Ah ah ah ah ah ah“ — it’s not exactly Swift’s most meaningful moment on record, but it probably is her greatest five-second sheer sugar rush. When she does get back to using her words, they’re good ones — an evocation of a free-and-easy group lifestyle that comes off as part social critique, full embrace. Hearing Swift sang “The best people in life are free,” whether she was being ironic or real about that, it came off as almost the antithesis of the hyper-romantic “Love Story” ethos… definitely the new Taylor coming to the phone. 

Swift used to count as a country star in her early days, but never really indulged in what we’d call “country-rock.” She did a little bit, though, in dribs and drabs on the “Folklore” and “Evermore” albums, where the laconic quality of a few of Aaron Dessner’s in particular lent itself to something that felt a little like the laid-back early ’70s style. One of the more obviously fictional narratives she was trying out, “Cowboy Like Me” has her as an unsentimental grifter in some unnamed resort area — I’m picturing Montana — who meets and falls for someone in the same shady line of non-work. It’s good that Taylor doesn’t really believe that “forever is the sweetest con,” and good that she’s stretched out to the kind of writing where she can create a character to say it.

After her second album, “Fearless,” Swift had an album of the year Grammy but also a reputation as someone who only wrote vindictive songs about ex-boyfriends. (There are people who still believe this, to this day. You should not have these people as your friends.) So it was the beginning of a correction in the popular mindset when, for her third album, “Speak Now,” she made a point of writing a song for an ex-boyfriend in which she took credit for what went wrong and expressed apologies and regrets — normal human actions, in other words, for someone who was not the narcissistic teen wraith some of the culture had set out to make her. All image adjustment concerns aside… damn, this is still just a lovely song, isn’t it?

This is a kind of sequel, in spirit, to “Blank Space.” In that one, she was still playing at being the bad girl, for satire. By the time of “Reputation,” she was doing it not so much for laughs — this is an “I could eff you up, seriously” song. No wonder it was such a highlight of her 2018 tour; the song rocks, and could manhandle a stadium with it as well as handled a single man.

This marked the beginning of the bonus track phenomenon for Swift, serving as the leadoff to the expanded part of the debut album’s deluxe (and, now, only) edition. In a career full of literally hundreds of hooky choruses, “I’m Only Me When I’m With You” has one of the hookiest. One thing unique about it is how the last part of the chorus lands on an instrumental guitar-and-fiddle riff, not a vocal climax — not the usual way to go, but Swift has never been one for playing exactly by the rules. Remarkably, this wasn’t even released as a single, and it didn’t last long in her live sets (although she did pull it out once as a surprise on the Eras Tour). For almost any other country artist, this would have been the absolute banger and obvious encore in their live show for the next 20 or 30 years. For Swift, it was more like an asterisk, but one that’ll bring a full-on dose of exhilaration when you remember to go back to it.

The sad sequel to “London Boy” that a lot of fans hoped they’d never get, but it certainly is one of her most transfixing recent songs, now that we’ve got it. Swift doesn’t devote a huge amount of time on “The Tortured Poets Department” mourning the relationship this one is generally understood to be about — she has even more recent fish to fry — but she doesn’t need to, so much is wrapped up into this song. It’s easy to imagine this breakup song being treated in the production like a solemn Aaron Dessner acoustic ballad. But co-producer Jack Antonoff is sort of counterintuitive in the sound of “So Long, London,” as, after a breathy intro, the pulse underlying the tune goes into what feels like quadruple-time, and stays there, so her post-mortem on a relationship and city that are lost to her feels almost as exciting as it is utterly exhausted. (It’s also ironic that the song’s heart is racing so fast when, a la the similarly themed “You’re Losing Me,” there are references to useless CPR.) “I’m pissed off you let me give you all that youth for free” is one of the most devastating lines in the Swift catalog, for anyone at a point in their life — and possibly women especially — to be counting the ticks of the clock.

It got a little confusing, for non-hardcore Swifties, trying to figure out which characters in which “Folklore” songs were which, after she revealed some of them recurred and had payoffs from one tune to another. Does the couple that shares a sweter together stay together? Did they come back together years later, as the pining outro strongly suggests? What we can say for sure is that Taylor Swift firmly cemented what Mister Rogers first promised: the cardigan as a signifier that everything is going to be all right.

This list needs a Christmas song, and you know it’s not going to be “Christmas Must Mean Something More,” at least not without a lot more spiked nog. Lucky for everyone’s personalized holiday mixes that Swift did eventually follow up her early Christmas EP many years later with a sentimental one-off (“Christmas Tree Farm”) but also, more significantly, this fairly unsentimental ode to hometown ex sex during the holidays. Like much of the “Evermore”/”Folklore” cycle, we can take this as an act of imagination (i.e., there is no mention of where the paparazzi are going to go while she and her old classmate briefly reignite some embers just for the hell of it). But all the mixed, pragmatic feelings that come up over the course of the song sure feel lived-in. Ho ho sigh.

Back in the “Fearless” days, we occasionally got Taylor Swift, the rock singer. (Arguably, we still have her, just without the rock arrangements.) The prime example was this track that pitted the polite guy who does everything right, who inspires no passion at all, versus the apparent scoundrel she was forced to leave behind, who made her want to stand in monsoons. Rock ‘n’ roll was played as a character trait for Mr. Passion, versus the string quartet on the verses that represented Mr. Right. Hearing those slamming guitars kind of fade in, the way they occasionally do on hits like “I Touch Myself,” was a nice way to alert the listener there’s a storm coming. However exaggerated the differences in this triangle might have been, it was only album 2 and Swift was already wanting to signal she wasn’t completely the Nice Girl portrayed on album 1.

At 6 minutes and 44 seconds, it’s still the longest song she’s released that doesn’t actually announce its running time in the title. And as a slow burn, it ends every second of the anger, sorrow, shame, lashing out and self-reclamation it unleashes. “Dear John,” about a character that the title does not leave too much cryptic mystery about, details the worst night she ever had that involved someone showing up for her party instead of missing it. At the time, it felt jolting well beyond expectation, that after the kiss-off experiences detailed in her previous album, she’d moved on to unabashedly detail what she considered a far more damaging experience. In retrospect, it doesn’t play as quite as musically furious a ballad as it seemed at the time, but it still packs a hell of a punch. And she still means it: One of the bonus tracks on the “Midnights” album, “Would’ve, Could’ve, Should’ve,” is clearly intended as a 12-years-later sequel, with certain numerological connotations that give her meaning away even if the lyrics didn’t. In Swift land, there are certain things you never get over — a curse, but for the purposes of art, also a blessing.

This will be the new climax of the Eras Tour when it resumes, post-“Tortured Poets”… won’t it? It’s about the Eras Tour, as the footage in the lyric video (above) makes perfectly clear, in case anyone didn’t get it. The odd factor is that, yes, it’s also about what a terrible time she was having on the Eras Tour, but only a small part of it, we can see in retrospect, figuring out the timelines. Swift isn’t really holding it against us as a mass audience that we didn’t recognize how miserable she was; it’s a statement of prowess, that she was mastermind enough to pull the wool over our eyes with all that performative joy. The song doesn’t speak to how positive she is presumably feeling now, but as a statement of purpose, it’s timeless. Once broken, always broken, but always covered in glorious show-biz armor. And, it’s set to a beat Giorgio Moroder would be proud of.

One thing that Swift didn’t have a lot of in her catalog: 6/8 waltzes. Situation rectified! It’s a wedding song for people who don’t intend, right away at least, to get married — there’s even a fakeout wedding scene in the middle of the song that ends with them vowing in front of God and onlookers to be, well, lovers — but anyone who wants to use it for actual nuptials probably gets a pass. It’s just universal enough to get that kind of usage in American customs and rituals, but you have to savor the bits that are pure Swift, whether it’s the guitar-string scars on her fingers or her custom-made vow: “Swear to be overdramatic and true.” Wait, is it her entire public she’s pretend-marrying, as well as this guy?

One of her most bracing, wounded, lacerating songs since “Dear John.” When she’s not impugning a certain ex’s manhood, she has questions, so many questions, in the face of an inexplicable ending. Like: “Who the fuck was that guy?” And, in the epic bridge (or is it a coda?), where suddenly a simple piano ballad explodes, more unanswered queries: “Were you writing a book? Were you a sleeper cell spy? In fifty years, will all this be declassified?” It’s the perfect song for anyone who ever felt like a passionate love affair ended in mystery, even if not everybody was dating someone dressed like a Jehovah’s Witness. In the end, she takes a kind of bitter comfort in the one thing she can be sure about: his tininess.

This is not necessarily the song you want to go back to constantly for pleasure now, but what a pleasure it was in 2016 when Swift used it to explode her own mythos, in one of the great power moves of modern pop. Her goal, she said, was to take every terrible trope that was being spread about her (hey, didja hear she was a serial dater?) and own it in a prideful anthem of ill will. And she did it magnificently, playing her public like a violin, including the ones who mostly got it and even the smaller portion that was left puzzled by her pop variant on country music’s classic “Your Good Girl’s Gonna Go Bad.” The satire was broad, but effective. Unfortunately, looking at the generation of influencers that’s arisen since, it’s not clear that some of them didn’t just take this spoof as a how-to manual.

“I’ll be your mirror,” the Velvet Underground once sang; this is Swift following up with: “Let me count the ways.” The Antonoff-cowritten “Folklore” track really does qualify as “shimmering,” for lack of a less obvious word. But deceptively so — Swift obviously doesn’t mean to suggest that serving as a pure reflector to the world’s varying wants and needs is a healthy thing, even though she sounds awfully darn pliant about the prospect within the confines of the magical music. This one has been compared to the Sundays and other prettily guitar-based indie-pop groups of yore, with a lulling electric guitar and a missing drumbeat you keep expecting to kick the song further into gear at any moment, in vain. It’s all so lovely — the funny thing is, in coming up with a song about being a people-pleaser, she came up with one of her most legitimately ear-pleasing tunes.

I’m going to out on a limb and boldly posit this as by far the funniest song Swift has ever written — and yes, despite her reputation for earnestness, there is some competition for that. When “Midnights” came out, there were some humorless scolds who laid into this song’s exaggerated statements of self-satisfaction and cosmic comeuppance as if they were to be taken completely seriously… as if “Karma is a cat / Purring in my lap ’cause it loves me / Flexing like a goddamn acrobat” isn’t some of the best comedy that anybody has written in any recent year. But acknowledging the levity of the writing doesn’t mean that Swift probably isn’t also completely serious, in some ways: The song is a victory lap, or maybe a vindication lap, of sorts when it comes to how mutual fortunes have swung around in certain circumstances. And no doubt she does believe that the arc of history bends toward justice for those with a moral center. Still, the awesomely clever co-production touches of Antonoff on this tune establish it as a soft banger. And it make for a great sequel to “I Forgot You Existed,” in which she contends that fate itself did not forget.

This ballad has one gut punch after another, especially by the time she gets to juxtaposing alleged quotes from the “Holy Ghost” who she suggests slipped out on her: “I’m combing through the braids of lies / ‘I’ll never leave’ …/ ‘Never mind.'” The thick, sad irony also allows for “legendary” to be rhymed with “momentary” — not the completion of that couplet any hopeless romantic is looking for. The cowardly lion is credited with a “valiant roar” in one line and “a bland goodbye” in the next — the instant diminishment just keeps on coming. Bringing up an older relationship, she sings, “I thought I was better safe than starry-eyed.” But what if neither pragmatism or passion pays off? Then she’s got one of the Lyrics of Her Life.

If there’s any track on “Folklore” that’s been a little bit too slept-on, it might be “The 1,” a humble little masterpiece hiding in plain sight right there as the opening track. Why does this not get more love? Maybe it’s because of its very unassuming nature, which is actually makes it great and an essential part of the Swift canon. Lord knows she has given fans dozens of songs in which love is understood as an urgent matter of life and death. Here, it’s like, “Eh — would have been nice to have seen that one through to the end to see how it turned out, but no biggie.” That might be one of the ultimate signs of maturity in her writing, that the woman who made wuthering heights her lyrical brand can also sweetly say “c’est la vie” and make that work for a terrific song, too. Except, maybe the woman doth not protest enough — there’s a touch of melancholy in the unusual chord changes that she or Aaron Dessner built into the track that let you know the wistfulness runs deeper than the acceptance. Meanwhile, I suspect there’s a musical joke embedded in the title, which is written as a numeral, the way a musician would render it, versus “the one.” At the end of the chorus, the word “one” begins on the last note of one bar and slides over to the next, where it lands on… you know it, the 1. It’s like an additional subliminal tip-off that the guy that got away both wasn’t and was the one.

Listening to the “Folklore” album, you could jump to assume that “Gold Rush,” like some of the other songs, is character writing. Otherwise, why would Swift be coming up with a song about someone who’s even prettier than she is, whose sheer charm takes up all the oxygen in a room — something that can’t be happening a lot to one of the most sought-after pop superstars in the world? Unless there was a romantic partner in her past who actually fit that bill… someone whose “hair (was) falling into place like dominos”… It all starts to make sense. But even if you don’t read that far into it, it’s a phenomenal song about the price being paid for being around that kind of charisma being too high to pay, whoever the charmer might be.

The finest song from Swift’s first album is an idyllic vision of an America where screen doors slam behind happy families and innocent teen lovers, who keep their late-night phone calls on the down-low “’cause it’s late, and your mama don’t know.” Imagine such a wonderful place exists — it’s easy if you try. Yes, it’s a song of puppy love, but maybe more importantly, it’s a Taylor Swift origin story. The premise of the lyric is that the developing couple, who are working up the courage to kiss, does not have “their song” yet. (They may have their artist, Tim McGraw, but that’s different, right?) So the tune ends with her sitting down to put pen to paper to write one, instead of passively waiting for something suitable to come up on the radio they can adopt. Mostly, you’ve probably thought of this as a frilly crush song — and it’s a great one of those, too — but what it really is first and foremost, right under our noses, is a declaration of young female artistic agency.

It’s like the girl from “That’s the Way I Loved You” grew up, decided to go back to the bad boy after all, and threw it in everyone’s faces — not just her family’s, but the general public’s. We can understand this to be about one of the most interesting relationships Taylor Swift has ever had: her love affair with the court of public opinion. Musically, this sounds like it could be from the “Fearless” era, but only the Swift of 2024 would be bold enough to have written a song while in the throes of a romance that Swifties did not approve us, lashing back at the pearl-clutchers with the most amazing rant she’s ever written: “I’ll tell you something about my good name / It’s mine alone to disgrace / I don’t cater to all these vipers dressed in empath’s clothing / God save the most judgmental creeps / Who say they want what’s best for me / Sanctimoniously performing soliloquies I’ll never see / Thinking it can change the beat / Of my heart when he touches me.” She may not still feel that way now, based on what we’ve seen play out, but God bless her for preserving the eff-you moment in a song and letting the public hear it. Has a song ever been so pissed off and so full of joy at the same time?

First of all, Taylor, thank you for writing a song about crying in the gym, not crying in the club. We’ve had enough of those, and type-A personalities who emphasize cardio over wanton night life need their breakup songs, too. This isn’t one of the most poetic numbers on “The Tortured Poets Department” — not with “Fuck it, I was in love” and “Fuck it if I can’t have him” repeated over and over, as lyrical mantras — but it’s got one of the best grooves, perfect for any workout queen’s most depressed cooldown.

Swift has plenty of superior instances across her many records of breakups that sound like the end of the world. But she doesn’t have many of them that sound like a party. “We Are Never…” is the best bacchanal in her catalog. I’m not sure I want to join the exact celebration that is happening in her music video for the song, because furries are scary. But the way Max Martin and Shellback stacked her vocals on this fizzy delight of a song clearly aurally indicate that Swift is capable of having a freedom soiree all by herself. Everything here clicks into place for a start-to-finish perfect pop song, from the peculiar stop-and-start opening guitar riff to the cheerleader-style chant that makes the chorus one of the great modern pop sing-alongs. Even all the indie bands whose records her ex thought were much cooler than her love this song. And, of course, embedding a voice memo late in the track, one in which Swift seems to be spontaneously describing a recent split with language that will make its way into the song title, is just a hilarious power move.

Swift already did this I’m-a-righteously–scary-person theme to perfection once, with “Mad Woman,” but “Who’s Afraid of Little Old Me?” is well, more perfect. For anyone who ever wanted to demonize her — and clearly, the Kim and Kanye backlash themes of the “Reputation” era still register strongly for her, six years later — she’ll gladly take on that demonization and raise you one. (Well, at least in the confines of this song, before she goes back to being the world’s greatest and possibly most sincere people-pleaser on tour.) In this seriocomic number, she’s a witch, a wraith, a child-poisoner, the little old sorceress who lives down the lane, a dangerous circus animal, and a hoot. Except these lyrics really sound frighteningly serious at times: “I wanna snarl and show you just how disturbed this has made me / You wouldn’t last an hour in the asylum where they raised me.” It’s good to know that the world’s favorite cat lady hasn’t exactly let herself be declawed.

Surely you know the story behind this, among the greatest of all “answer” songs. Girl meets industry blogger boy; industry blogger professes admiration until her somewhat off-key performance at the Grammys causes him to spontaneously declare girl’s career completely over; girl writes song pushing back on that, landing a triple-platinum single with her response. And she does it with a pointed return to country music, something she had already effectively moved past in everything but name by the “Speak Now” album, singing in a childlike tone that made her sound like a little hillbilly David, taking on an influencer Goliath. Probably not many of those millions of fans paid close attention to the exact background to the lyrics. But apart from the “I can’t sing” bridge, this song was applicable to anyone who’s ever felt bullied in life, by a classmate, boss, family member, etc. It’s too bad it predated the social media explosion, by a little: “Mean” is really the Twitter National Anthem.

A sense of recovery from trauma figures into a number of Swift’s songs, most of all this “1989” closer that represented a one-time co-write with indie artist Imogene Heap. The word “clean” is used with two different meanings here, although pretty much toward a common end. It’s clean as in the feeling of taking a prolonged shower after the accumulated grime of a sucky relationship… or as in getting clean, kicking an addition to toxic love. Either way, there’s been some bad juju at play, and somebody — Nurse Heap, maybe? — is helping take the curse off. What prompted Swift to co-write this calming, cathartic ballad is probably nobody’s business, but a lot of listeners have brought their own ugly experiences or addictive experiences to bear in appreciating this bath-salt ballad.

A stunner, buried in the back half of the double-album version of “The Tortured Poets Department.” Buried is used deliberately there, as Swift uses lots of death imagery to describe the end of a relationship — “How the death rattle breathing / Silenced as the soul was leaving” — that calls back to another recent song that would seem to be about this same scenario, “You’re Losing Me.” Perhaps one of the best and moments in her entire catalog comes when she spells things out by singing, “My beloved ghost and me / Sitting in a tree / D-Y-I-N-G” — a chilling bridge even if you don’t at first catch the clever allusion to Jack and Jill K-I-S-S-I-N-G. The song really has two subjects, to go along with the markedly different chord changes in the verses and chorus: public fascination with the reasons for a breakup, and the singer’s own puzzlement over how things came to such an ignoble end.

She has some good theories about that; the great line “He was a hothouse flower to my outdoorsman” almost feels like all the explanation we need. Yet she finally answers the title question with a candid “I still don’t know.” What she is certain of is that the cycle of romantic demise is repeating: “It’s happening again,” she warns… probably not intending to repeat a spooky catchphrase from “Twin Peaks,” but in the context of this haunting song, it’s just as ominous.

It’s hard to pick a favorite song from among those released as part of the glorious 31-song data dump that is “The Tortured Poets Department: The Anthology,” but many fans have understandably settled on this one, which got elevated from its originally advertised bonus track status to a real touchstone track. It hooks you from its high-concept start, wherein Swift finds herself following the actions of a recent ex who forgot to turn his location tracking off, as she follows him into a old mutual haunt called the Black Dog (not to be confused with the “black dog” that is depression — or is it?). Although she probably doesn’t have the electronic means to know what songs are being played in the bar, she’s sure it’s an old emo hit they shared as “their song” for a time… one by the 2000s pop-punk band the Starting Line. And she hopes it’ll be ruined for him. There’s a small, specific strain of songs that are about people’s experience of other songs — think “Tim McGraw”! — and this is a great one, speaking to how shared music tastes take on a different tenor when we’re forced to be on our own. The best part is how the music keeps threatening to rise to its own emo climax, as she wishes her former beloved the shittiest possible time.

We may never get an accounting from Swift of what “Bigger Than the Whole Sky” is about or was prompted by. But we don’t really need a delineation from her to find it one of the most profoundly moving pieces she’s ever written. On a casual listen, it appears to describe a breakup, a death, or a breakup that felt like a death. Many believe it describes a miscarriage, and it’s pretty hard to hear it any other way once you’ve considered that take. The death of any child is certainly also a consideration, and comments from fans who’ve had to experience these tragedies show that the ballad holds up and has cathartic power under that weight. Along with “Ronan,” this is one of two numbers in the Swift catalog most guaranteed to bring on full-scale bawling, if given anything other than a casual listen. It wouldn’t be surprising if Swift feels the same way — it’s one of the few songs among her hundreds of compositions that she had never sung live… until she finally broke it out in honor of the fan who died of heat exhaustion in Rio de Janeiro. Dry-eyed listener, beware.

So much of the talk about the “Fearless” album was about the bracingly candid breakup songs, or embracing the fairy tale, in “Love Story,” and rejecting it, in “White Horse” (and “Fifteen,” for that matter). That was more than enough grist to get Swift the first of her four album of the year Grammy wins, this one while she was still a teenager. But amid all that high romance and higher drama, there’s something at least as enduring about the simpler ambitions of the title song, which just speaks — via a typically great melodic line — to being unafraid. It was followed by a career that has embraced at pretty much every moment what this early song title promised.

When “Midnights” first came out, with none of the songs pre-issued to the public, if you weren’t paying attention to video premieres or that sort of splash, you might have taken “Anti Hero” as one of the odder songs on the album, not a sure out-of-the-box hit. But in Swift land, slightly weird works. Even the initial minor controversy over the “sexy baby” line — is it cribbed from “50 Rock,” or is it infantilization — abated, as almost everyone took it for as funny as it was, in the course of a verse where Swift is imagining herself as a feared and hated monster who’s going to be taken down. It’s a song about self-loathing, as she described it, and imposter syndrome, and clinical or unclinical depression… and wouldn’t you know, it’s also a deeply funny bop. That we can have such a bizarre amalgam at the top of the Hot 100 for weeks on end proves that, thanks to Swift being able to sell something this idiosyncratic, these are strange and wonderful times.

Swift’s partner in this deeply sexy track is cosplaying as James Dean, at least in her mind, and she’s cosplaying as… Taylor Swift? Thee’s no duet part to let his hear point of view, but she does attest that he likes her “good girl faith and a tight little skirt,” and there’s no reason to believe she’s misreporting what turns the guy on. Honestly, Swift has never written a less deep song, and depth has never mattered so little, either. Max Martin and Shellback put some of their computer programming instincts aside to start this off with an R&B electric guitar riff that immediately sucks you in. And once the kind of light-disco-martial beat kicks in, the track feels like taking an open-top drive around Miami with Don Johnson and Philip Michael Thomas, only they’re a horny hetero cis couple.

Swift was playing with a lot of fresh tricks on her “Reputation” album, and well, from some hip-hop styled phrasing on her part to some harsher electronic sounds being brought in by Max Martin and Shellback, making their final appearance to date on a Swift album. But with her other go-to collaborator of the time, Jack Antonoff, Swift crafted the song that is the most conventional-sounding track on the album, and also ultimately the best: “Getaway Car.” While much of the rest of the album flits back and forth between a defensive posture against public perceptions and an embrace of secret love, “Getaway Car” is something else altogether: an open letter of intent to move on, sung by a Bonnie who’s about to ditch her Clyde, with no particular shame or guilt attached to her leavin’ feelings.

In some ways this might be the most hard-ass song Swift ever wrote — it’s pretty close to a taunt, to a soon-to-be ex. She’s describing the dynamic of how sometimes you need a fresh flirtation to pull you out of a failing relationship, and how that can take on serial form: “Don’t pretend it’s such a mystery / Think about the place where you first met me / Ridin’ in a getaway car,” she tells the possibly uncomprehending fellow. This is an uptempo track with a lot of fun to how it plays, but the haunting quality of the chorus melody makes it feel profoundly sad, too, like she’s not as tough as she sounds, describing an escape pattern that’s just destined to be repeated by her and others over and over. Anyway, if you were to read this as literally about her past, it’s something that the public record shows she’s clearly moved on from. The happy ending is inherent, leaving us this strangely wonderful combination of arena-rock and hardboiled, fatalist noir to enjoy as one of her most fascinating tracks.

No amazing amount of depth to this one; it’s just pure cotton candy, with a little emotional fiber sprinkled around the edges. Her fandom was in near-universal agreement that this should have been a single to accompany her planned “LoverFest” tour of 2019, but that summer turned out to be crueler than anyone imagined, so it was a smash only in an alternate reality — until an Eras Tour-driven 2023 revival that boosted it right to a belated No. 1. The kind of Vocoder-sounding part in the call-and-response verses suggests this bop has its real origin point somewhere in the vintage ELO era, and of course it’s hard for fans of a certain age not to think of Bananarama, who were also cruelty-tested once upon a time. But no one but Swift could turn summery seasonal-affective-disorder into something this grand.

This is not the first time Swift relegated one of an album’s better numbers to bonus-track status, although she usually makes the right editing decisions. But “Right Where You Left Me” is another case entirely from, say, even “New Romantics”: The “Evermore” deluxe-edition also-ran is flatly one of her best and most dramatic songs, period. As a song about not being able to let go of an obsession with a deceased relationship, it’s pretty close to being up there with “All Too Well,” even if the fact that it’s written mostly in metaphor lands it in slightly more intellectualized territory than that other favorite.

Playing the role of someone presumably other than herself for this one, Swift describes in calm, cool, clipped sentences how she was dumped by a beau at a dinner meeting, and then simply never got up from the table, herself; she’s been frozen in place there, a ghost, for years. (Lucky or unlucky for her, not a high table turnover rate at this place.) If you are obsessive enough by nature to have become obsessed with the obsession in “All Too Well” — show of hands? — then you’ll probably have lived “Right Where You Left Me” at some point in your life. Swift’s talky verses suggest the cadences of somebody who really has been only talking to herself for too long, and collaborator Aaron Dessner is a perfect foil in creating a tense, slow build toward a big chill. A bit of sad, distorted guitar at the end sounds like it might be being piped in from the alternate dimension the protagonist is slowly sinking into.

In its original, truncated form on the “Red” album, “All Too Well” already felt a fluid narrative, but stretched out to more than twice its length for a “Taylor’s Version” remake, its details and remembrances transcend any sense of linear narrative. The song’s story feels almost like a “Groundhog Day” of meditative pain in which the story will never end because the couple will just never stop breaking up, in her mind. (Well, it might end if the sister ever returned the damn scarf, but by this point she don’t need their closure.) It becomes almost like a chant, even more soothing than it is bitter.

Having effectively talked Swift into recording a 10-minute draft of the song with their longstanding, cult-like devotion to the tune, Swifties need to take it to the next level. You know there have got to be another 10 minutes’ worth of rough verses to “All Too Well” in a drawer somewhere. We need the full-on Gregorian experience of this song, right? It’s time to petition for “All Too Well (20-Minute Version).” (Could you even imagine the explosion of joy?)

It’s as eternally teenaged as anything Swift ever wrote, but that’s no reason to have to grow out of it. Adult life is full of nothing if not many equivalents to high-school friend-zoning. Who among us eer stops wishing we’d be seen for our true selves by the guy who can’t take his eyes off the cheer captain, whether for us that’s the boss, peers, a distracted spouse or a seemingly indifferent deity? To the end, we beat on — boats against the current, borne back ceaselessly into the bleachers!

But seriously, has there been anything more monstrously hooky than this in the succeeding decade and a half? Even the parts of the song that seem like they shouldn’t work — like the way that Swift adds extra, melodically odd lines to the second verse (“What you doing with a girl like that?” What you doing singing in a key like that?) — only masterfully set up the return to the chorus to end all 21st century anthemic choruses. It is all of human yearning and striving packed into a song about remembering to take your specs off so the kid next door realizes you’re a cutie.