Taylor Swift eras deathmatch! Making the case for the superstar’s best album

In a pair of cowboy boots, 16-year-old Taylor Swift stepped into Nashville’s country music scene, released her eponymous debut album and changed pop music. Swift’s debut is often written off for her excessive vocal twangs and banjo flourishes, but singles such as Tim McGraw, Teardrops on My Guitar and Our Song, which rocketed up both the country and pop charts in 2006, have stood the test of nearly two decades.

Many of the lyrical motifs that recur throughout Swift’s discography have roots in her debut: Cold as You’s pouring rain; Mary’s Song’s 2am time check; Our Song’s meta take on artistic inspiration. The sophisticated songwriting of her debut remains impressive but it was Swift’s expression of adolescent emotional intensity that connected with young listeners like me.

Today, with the likes of Olivia Rodrigo and Billie Eilish dominating pop, the idea of a teenager making music for other teenagers is commonplace. But in 2006, it was cohorts of middle-aged men who were writing the songs that represented the adolescent experience – the High School Musical soundtrack was the best-selling album of that year. For a generation, Swift’s debut was the first time we heard our experiences – painful loneliness, romantic yearning, even body dysmorphia – taken seriously in songwriting by one of our own. Katie Goh

Call the world’s great physicists and tell them to stop trying to invent a time-machine: it exists, and it is Swift’s second studio album, Fearless. Press play and you’re immediately transported back to high (OK, secondary) school, back to – as Swift herself puts it – “the bliss and devastation of youth”. Like school itself, the entire album feels like a cusp – not only was this an important step in Swift’s transition from country to pop, but the lyrics capture the push and pull of teenage life, a time when fairytales still seem possible but boys regularly lie about loving you.

Nowhere is this better reflected that in the song Fifteen, with a lyric so belt-able that you should be able to hook it through your jeans: “In your life, you’ll do things greater than dating the boy on the football team. But I didn’t know it at 15!” (And OK, elsewhere there is more than a little misogyny in this album – but it is the catchy kind!)

Also, we cannot and should not judge an artist’s greatest era by their hair, but it would be remiss not to shout out locks so golden and bouncy that you half expect three bears to storm the stage, promise to let Swift finish and tell her off for eating their porridge. There is a reason Fearless propelled an 18-year-old Swift to global superstardom and it’s because songs about fancying boys and them not fancying you back are the world’s greatest art form. I know it now – and I knew it at 15. Amelia Tait

Speak Now is the Fast & Furious of Swift albums: even its ballads move with a breakneck momentum. Largely forgoing the swooning country of Fearless in favour of driving, muscular power-pop, the songs here – written entirely by Swift, without co-writers – are finely and tightly constructed, heavy with tension and filled with surprising final-act perspective shifts. The near-seven-minute Dear John, a brutal and righteously vengeful assassination in ballad form, is just as spectacularly gripping as The Story of Us, a racing pop-punk kiss-off. Even the songs that are clear fantasies, such as the twee wedding-crashing title track, build to propulsive finales.

Each time I return to Speak Now, I find myself caught off-guard by just how exacting Swift’s knife was at this point in time. On Mean, she eviscerates critics with the same sharp, plainspoken poetics of her idol Natalie Maines of the Chicks. Enchanted pulls the wide-eyed fairytales of Fearless into the real world. Even the sneering pop-punk track Better Than Revenge – which has since been dinged by fans for its somewhat retrograde gender politics – is vastly better than it gets credit for, landing some brilliantly bratty blows (“No amount of vintage dresses gives you dignity”) and showing an early example of Swift’s skill for slipping into seemingly disparate genres at will.

Speak Now may be the forgotten middle child of Swift’s albums, landing right between beloved juggernauts Fearless and Red, but with each passing year it feels more and more like my favourite of her records: a breathless, exhilarating thrill ride. Shaad D’Souza

If Swift’s early-career flip of fairytale narratives had felt a little Disney, then Red is a Nora Ephron movie, assembling and magnifying precise details into swooping storytelling arcs. There’s a breathtaking sense of scale to its forward-thinking forays into EDM, dubstep and country-rock, with grand swells of emotion masterfully calibrated to hit pop’s bullseye. The notion of “happily ever after” is a false god, she had realised; what was real was to write a heroine bruised by love and holding on to fragments of hope, as she does on Begin Again. Or, in All Too Well, to deliver a relationship postmortem so richly devastating that Stanford university now runs a course on it.

She would later lean into villainy, but Swift during her Red era knew that a burn is most savage when masquerading as aloe: “Loving him is like driving a new Maserati down a dead-end street,” as she sings on the title track. And the album marks the birth of a Swiftian signature: the indelible goofy aside. There is no “I’m the problem it’s me” without We Are Never Ever Getting Back Together’s “like, ever”. It takes a 22-year-old’s brilliant audacity to claim a whole colour of the rainbow, and on Red, Swift seemed made of starlight, channelling intense emotion and creative hunger into her first truly great era. Owen Myers

When Swift announced 1989, she described it as her “very first documented, official pop album”. And what a pop album it is. Polished and precise, 1989 eschewed contemporary musical and cultural touchstones, its nostalgic bent towards stadium-sized power pop and crisp synthesised electronics helping Swift carve out her own niche in a landscape that was dominated by R&B crossover and EDM.

While such grand musical vaults and gimlet-eyed determination to conquer the charts resulted in Swift dialling down some of the diaristic specificity found on Red, it also made for huge, all-encompassing choruses: the impeccable Italo disco of Style (one of her best songs), the swooning heartbeats of Wildest Dreams or the euphoric chorus of New Romantics. Swift’s storytelling also bled into the production: the fizziness of Blank Space, with its winking pen-click, allowed her to self-mythologise with humour rather than bitterness, while the musical world created in Out of the Woods transports you to the moment in her relationship when the brakes were hit too soon.

Of course, 1989 was also the slightly regrettable era of girl squads, feuds and “please welcome to the stage”. But it should be remembered for being Swift’s boldest musical leap. It’s a risk that few pop stars would take today. Alim Kheraj

When I first heard Look What You Made Me Do, the lead single from Reputation, I cringed. Gothic melodrama sounded so gauche on Swift: the lyrics’ emphatic cadence didn’t suit her voice, and its brattiness was completely out of sync with her usual ingratiating sleekness. In time, I realised that was part of its genius, especially when taken as part of Reputation. Made following Swift’s annus horribilis (backlash against her surface-y feminism and accusations that she was some sort of Trumpian accessory; her beef with Kim and Kanye pushed to boiling point) Reputation was a comic heel-turn that refigured Swift’s embattled persona as a panto villain. But her dragged-up sixth act ended up freeing her from some of the strictures – personally and societally imposed – that had landed her there in the first place.

Feeling hated gave Swift less to lose. It let her grow up: she discarded the likability and chasteness that had defined her career to take bigger swings, unleashing emotions she had previously held in: carnal desire, rage, unfettered vindictiveness, F-you-I’ll-take-my-ball-home. She tried out different voices and welded her songwriting to rap’s hard edges in a way that, unlike most pop star-goes-rap grifts, actually worked. On her next album Lover she would sing explicitly – and somewhat obviously – about the double standards that women face; but it’s more effective here, where you feel her anger in the deliciously petulant smack of I Did Something Bad, Don’t Blame Me and that furious lead single. (The big tantrum energy, at least on Reputation’s first half, feels pretty reasonable now when you think about what she was subjected to in the media.) It also generated her most fun live show, taking Kim Kardashian’s “snake” barb and blowing it up into a gigantic inflatable serpent called Karyn that loomed from the back of the stage.

Being at rock bottom, of course, also gave Swift everything to gain. Reputation dodges bitterness because of its devotional second half, where she seems stunned and grateful to have found love in the middle of all this angst. The gasping Dress (her first actually sexy song) and the joys of quiet privacy in New Year’s Day are among her very best. Swift thrives when she feels things extremely deeply, as she does here: Reputation is the flash of her armour and the wounded heart behind the breastplate; she lashes out but lacerates herself as much as anyone else. The title of Swift’s sixth album reflected on how perceptions of her had “never been worse” – but today she can stake her creative reputation on it. Laura Snapes

As the quote-tweets on that viral Wango Tango performance of Me! from 2018 can attest, Lover is not necessarily the album that most Swift fans are most desperate to hear live. Nevertheless, when you pluck away the layers of radioactive Kraft-slice cheese, Swift’s seventh effort is a record of endearing significance, a kitschy moment of triumph after she left her old record label, a move that prompted her to re-record her back catalogue.

Shedding the reptilian skin of Reputation, Lover is all about rebirth, swapping moody revenge for synthy fun. Whether showing love to the LGBTQ+ community (You Need to Calm Down), poking fun at unhealthy gender norms (The Man) or espousing the virtues of dating someone British with knowing anglophone references (London Boy), Swift readily embraces sunshine and rainbows, leaning into the affirmation of newfound love.

There is some balance: Soon You’ll Get Better, about her mother’s cancer diagnosis, is a sobering moment of vulnerability, while the fragility of Cruel Summer, about the early dating stage of a relationship, is easily one of her finest songs, building to the kind of earnest staccato hook that is now her signature finishing move: “I don’t wanna keep secrets just to keep you!” Not every track is a must-hear but the beauty of Lover is what it brings to Swift’s sonic sandwich: texture, bite and a generous sprinkling of sugar. Jenessa Williams

At some point in the last decade, I resigned myself to the fact that I will follow wherever Swift leads me. Never has this been truer than on Folklore/Evermore, a two-album era containing many elements that I would usually find profoundly triggering – acoustic guitars! Self-conscious lowercase titles! Male vocalists! – yet continues to captivate me.

It didn’t hurt that Swift’s most introspective albums arrived during a time of great turmoil for me personally (yes, I am referring to the pandemic). But they also found her at her most relaxed. Minus the exhausting parade of Easter eggs and corporate tie-ins that preceded Lover, Swift’s surprise lockdown albums marked an unexpected but welcome handbrake turn. Whereas her storytelling had typically centred on autobiography, Folklore saw her expand her reach to encompass eccentric heiresses, murderous husbands and a three-song story arc about a teenage love triangle. (It is a testament to her evolution as a songwriter that listeners are as invested in the fictional Betty’s cardigan as they were in the much mythologised scarf of Red’s All Too Well.)

Elsewhere, familiar themes – longing, the loss of innocence, the moral decrepitude of Scooter Braun – are accompanied by cinematic orchestrations and sweeping melodies, not to mention three career-best bridges on August, My Tears Ricochet and This Is Me Trying. Suddenly staying indoors didn’t seem so bad. Joe Stone

Swift has made so many albums in so many different genres that comparing them is tough. But if you had to nominate one as her best, Midnights has a strong claim. It doesn’t have the immediate impact of the fizzing, angry Reputation or the sudden left-turn appeal of Folklore. It’s surprisingly subdued by modern pop standards: low on certified bangers, big on muted atmospherics (there’s even a hint of shoegaze about the guitars on Maroon) and restraint, as evidenced by the Lana Del Rey duet Snow on the Beach, which is so low-key that it upset Del Rey fans expecting a showstopping guest appearance.

But what it has in profusion is fantastic songs: You’re on Your Own Kid’s sharp depiction of the teenage Swift struggling to break out in Nashville; Anti-Hero’s small-hours self-loathing; the impressive combination of sweet tunefulness and spite on Karma. There are songs that display Swift’s skill as a writer – her depiction of a drunken conversation on Question…? suddenly speeds up and stops rhyming – and songs that deal in experimentation, not least the warping of her voice until it sounds male on Midnight Rain. It’s an album that doesn’t need to adhere to modern pop’s rules and standards because the material on it demonstrates Swift is miles ahead of her peers: a confident, mature victory lap. Alexis Petridis