Not sure how she become the biggest pop star in decades? Here’s a 101 from lapsed music critic Duncan Greive.

Don’t look at any one album – look at the trajectory

Swift started young. Like, really young. She first went to Nashville and tried for a record deal at 11. Her self-titled debut came out when she was 16, and was deeply informed by that town – it has a hearty twang and there’s a song simply named Tim McGraw. She could have had a huge career within those boundaries, but watch what she did instead. 

Next came Fearless, which shot the country full of pop-rock, most tellingly the Kelly Clarkson-ish ‘You Belong With Me’. Then the extraordinary Speak Now, entirely written by Swift, which starts to move on from country and takes in a naked Paramore tribute (‘Better than Revenge’). 

Her 2012 album Red nods at pop-dubstep via super producer Max Martin, while 1989 was pure pop maximalism, driven far more by synthesisers than guitars. It never stopped: by the dawn of the next decade she would be working with Bon Iver. It’s routine for artists to evolve – they’re criticised if they don’t – but there is a Lego-like structure and sequencing to Swift’s career which means that with every record (with the possible exception of the divisive Reputation) she has added new fans without losing those she came in with.

Her singles are not that important

While massive hits, the singles often sit incongruously within her albums. Her most powerful skill as a songwriter is her lyricism, which tends to cohere into narrative more easily away from the bright lights and big hooks, so her hits are seldom the songs her fans most revere. 

It’s telling that on her current Eras tour, she doesn’t play any singles from Speak Now, arguably her most beloved album. She treats singles the way a software company does free features at the top of its conversion funnel: they’re there to attract the largest possible audience, but she has something more powerful to sell you once you’re interested.

What really elevates her as a writer is the minutiae of her relationships and emotional life, in all its vivid specificity, which is what makes her fans relate so keenly to this untouchable billionaire. I interviewed her back when she had any cause to make phone calls to print journalists in New Zealand, and she explained the approach and appeal of her songs in a live context pretty well. “It makes me feel like none of us are alone, and that we’ve all had these similar experiences and we can be together in that,” she said. “We can stand there and make eye contact and we all relate to those words. And I think that only comes to me because I write songs about my life.”

The creative / business strategy is really singular

I wrote about this in my review of her stunning show in Melbourne last week: “The Eras tour is on its way to grossing $1bn, and has exploded the sense of what is possible in touring in multiple ways. Its extreme duration, the career-spanning conceit, insatiable demand despite multi-night runs at the biggest stadiums we have, a ballot just to buy merch and a concert film which obliterated the previous category record. When plugged into her “Taylor’s Version” album re-records, which adroitly stared down a powerful music manager and a private equity titan, the creative and business vision is as dazzling as the show.” 

Just as Apple seemed to operate in a different paradigm to Dell and HP, Swift’s concept of how she releases and tours music feels distinct from and more strategic than almost everyone else in pop music.

Few artists in history have studied and fed their fans so well

Up until the character-driven Folklore, Swift wrote almost exclusively in first and second person, about the specific experiences of her own life. Because her movements and relationships are so scrutinised, when she writes thinly veiled songs about her current and former partners, analysing them proves irresistible – most notably the devastating ‘All Too Well’, about her relationship with Jake Gyllenhaal. 

Her albums and their packages are studded with clues, nods and signals, devoured by fans and able to be endlessly re-examined. This does not always manifest well, as with this bizarre 5,000 word New York Times essay which conspiratorially laid out a case for why Swift – an LGBTQ ally, sure, but very straight – has already come out as queer through coded messages, despite her monstrously public current relationship with Kansas City Chiefs tight end Travis Kelce, and having only dated men. 

Overall though, the way she listens to and then echoes back the passion of her audience is a textbook example of how to maintain a fandom which operates at massive scale and for many of whom is almost an identity.

Ten songs that explain her scope and appeal

Ultimately, all of this is built on and only plausible thanks to her songs. She is wildly prolific and incredibly consistent, and has built an elaborate and resonant world which relates to the one we live in only so much as comic books do. That is, we have heroes (almost always Swift) and villains (mostly, but by no means always, her exes). We have small towns and picket fences and drives on country roads and glances across crowded rooms. 

It’s real life, but a fantasy of it, delivered in such a way that when you’re really in one of her songs, whatever exists in your life shrinks to invisibility. This is true of many great artists, I know. But it’s true more often and at giddying scale with Swift.

Here are 10 songs which capture her appeal (to me) (here they are in a playlist, not all in Taylor’s Versions because some of those are notably worse, sorry!)

‘Our Song’

Comes in with a fiddle, soon giving way to banjo – sonically this is where she came from but would seldom touch again. But Our Song is a shockingly compelling piece of songwriting too, the highlight of her debut and the kind of structurally and melodically immaculate composition she would hone to perfection over the next three albums.

‘Fifteen’

The story of Abigail, who “gave everything she had to a boy / who changed his mind” has not aged well in terms of its conceit, people typically think of women as having more than simply their virginity to offer the world. But it tells a story of the milieu she grew up in with startling precision, taking you right back to the stakes and emotion of high school.

‘Enchanted’

I remember being devastated to discover this was written about the hyper-dull singer for Owl City, but if you can set that aside this is an absolute thunderbolt, wall of sound guitars and a hook overflowing with big crush energy.

‘Long Live’

Speak Now’s closer is something of a twin to ‘Enchanted’, looking back across a relationship rather than imagining one from its beginning. Its lyrics are literally fantastical (“fighting dragons” etc), but that’s why it conjures the giddy feeling it aims for so potently.

‘The Lucky One’

Red is so loaded with irresistible guitar pop songs that picking one feels cruel and arbitrary. Today I’ll go with ‘The Lucky One’, an early character-driven slow-burn about a star who gets exactly what she wants and finds it something of a curse (who could that be?)

‘New Romantics’

Moody, near-Robynesque verses which erupt into an ebullient chorus. A career peak for most pop artists; a near-buried 1989 bonus track for Swift.

‘Cornelia Street’ (live from Paris)

On Lover this is a propulsive minor-key synth pop song, which is great – but the live acoustic take (presaging the Era’s tour surprise songs) is so natural that it feels almost like the definitive version.

‘The Last Great American Dynasty’

Her long relationship with English actor Joe Alwyn seemed largely happy, depriving her of the flirting and venom which defined much of her earlier work. Hence, perhaps, the need to project drama into imagined narratives. ‘The Last Great American Dynasty’ talks about a wedding that was “charming if a little gauche”, and tells a brilliantly economical old timey story starring someone who seems a lot like Swift off a leash.

‘Renegade’

Released in 2021 on an album by Big Red Machine, this is emblematic of how stunningly prolific she was in the Folklore/Evermore/Taylor’s Versions era. Dozens of songs, near-uniformly strong – but ‘Renegade’, with a swirling organ and skittering live drum beat, is one of the very best, despite languishing in relative obscurity.

‘All Too Well’ (10 Minute Version)

A towering work, with verse after verse after verse of incredibly intimate detail, covering the up and then way down of a relationship. It gradually grows into a gut-howl, and then a gorgeously delicate coda. Peerless, imperious songwriting and performing, one of the greatest feats of chaotic imagination of 21st century pop music.