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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

Fearless (2008)

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 (2010)

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 ᴀssᴀssination 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 тιтle track, build to propulsive finales.

Swift in 2010. PH๏τograph: Matt Sayles/AP

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 pᴀssing year it feels more and more like my favourite of her records: a breathless, exhilarating thrill ride. Shaad D’Souza

Red (2012)

If Swift’s early-career flip of fairytale narratives had felt a little Disney, then Red is a Nora Ephron movie, ᴀssembling 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 ᴅᴇᴀᴅ-end street,” as she sings on the тιтle 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

1989 (2014)

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.

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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-encompᴀssing 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