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The Evolution Of Taylor Swift In 20 Essential Tracks

From country prodigy to pop superstar to disgraced figure to comeback queen - there's been no career in history quite like Taylor Swift's. Words by Chris Lewis

By Chris Lewis, 20/8/2019

Taylor Swift is an empire, and no empire is built without blood being spilt. Taylor has lost friends, fans and lovers in her journey from a precocious Pennsylvanian folk singer to global juggernaut of pop music.

She’s played the game better than most — not that the phrase ‘playing the game’ is any way derogatory, it’s more that Swift’s own musical interests and growth have simply paralleled her own development as an artist and a woman.

Growing up as a Nashville songwriter there are only so many chords and topics you are typically supposed to cover, so it’s not surprising that someone so sure of their ability and ambition would break the constraints and go rogue.

And what happened from there…well every man, woman, and snake has their opinion. Her acolytes swear by her genius, whilst her skeptics are resolute in her duplicity. But putting the fickleness of fame aside, what everyone can settle on indisputably is the success of one of our generation’s supreme songwriters.

This paragraph could list figures and awards and attempt to justify her ubiquity over the last decade, but her existence as a musical tour de force makes that a superfluous exercise. In her typically unapologetic style, Taylor Swift has become one of the few cultural icons to transcend her medium since Madonna. And with her long awaited seventh album Lover arriving this week, we celebrate the evolution of one of music’s most interesting figures.


‘Should’ve Said No’ (2006)

Taken from her eponymous debut album, ‘Should’ve Said No’ is a slice of Nashville sugar and a window into a prodigious songwriter finding her voice. The righteous anger that underpins the song would become a template Swift would return to many times over her career, but never again would it feel as raw as this particular reclamation of power.

The violins and banjos might make it sound like we’re in for a real hoedown, but the heart-on-sleeve pain in Swift’s voice turns this into a very public takedown of a cheating lover — a theme that she would continue to refine. I kinda miss the banjos, to be honest.


‘Love Story’ (2008)

Surely it’s meta — she’s singing about Romeo and Juliet in a self-aware way, borrowing tropes from classical love stories to spin a tale on modern love. Surely. Either that or it’s the sound of an 18-year-old accomplished musician feeling out her own lyrical capabilities and falling back on reliable clichés as she finds a new gear in her melodic treasure chest.

‘Love Story’ is her first anthem and marks the first metamorphosis from country prodigy to pop star, and it’s by walking this line that she would create her US$360 million dollar brand. This is her genesis.


‘You Belong With Me’ (2008)

Casting herself as ‘the other girl’ for one of the first times in her career, ‘You Belong With Me’ is the simple ‘choose me, not her’ scenario that played out in many Freddie Prinze Jr. films circa 2000. It’s still Nashville through and through, but you can start to draw a straight line correlation between her leaving the South and dropping the banjo.

Interestingly, Swift positions herself as the down to Earth option for the man; she’s not on the cheer team, she wears t-shirts (not short skirts) and she *understands* him more than his cold-hearted girlfriend. The song might be filled with extremely dated (and decidedly anti-feminist) clichés, but the bridge-chrous progression still slaps. You could even argue that it’s sad she doesn’t sing with the same wanton passion anymore, but age does that to you.


‘Mine’ (2010)

‘Mine’ might be the most perfect country pop song this century. It plays off the stadium pop rock dynamics that Keith Urban made his trillions from, but buries a narrative about a guarded young woman learning how to fall in love just under the surface.

It’s Shakespearean in structure — beginning with our lovers’ happily ever after before introducing a fourth act tragedy, only to resolve in the last verse just as we’d nearly lost hope. “You made a rebel of a careless man’s careful daughter” is the first lyric in her canon that hints at her generation-defining potential and the tightness of the composition is the sound of her arriving to commercial pop music as a conqueror.


‘Dear John’ (2010)

What kind of scarring does John Mayer have from this third degree burn? Coming in at just over six and a half minutes, ‘Dear John’ is more akin to therapy than pop music. Or it’s at least a crushing cathartic release for Swift, a woman with eyes wide open who can see manipulation she was once blind to.

Musically, it’s one of Taylor’s most monotonous compositions, but it’s worth wondering whether this is by design. This is an artist who can write three chart-topping melodies before breakfast, so it stands to reason that if she writes a droning folk song it’s because she wants her audience’s attention to be squarely on her lyrical exorcism:

“You are an expert at sorry,
And keeping the lines blurry
Never impressed by me acing your tests
All the girls that you’ve run dry
Have tired, lifeless eyes ’cause you burned them out
But I took your matches before fire could catch me,
So don’t look now, I’m shining like fireworks over your sad, empty town”

It’s also important to note her focus on youth and that she was too young to be involved in the situation, reflected in the repeated refrain directed at Mayer that “you shoulda known”. These are words that resonate more than ever in a post #MeToo world.


‘Speak Now’ (2010)

Would she release this song again if she had her time over? A woman, so sure in the fact that a man is marrying the wrong woman, uses the traditional “speak now or forever hold your peace” moment in the church to spectacularly gatecrash and ruin a wedding. Coming back to ‘the other girl’ template, Swift turns it up to 11 and where ‘You Belong With Me’ comes off like a coy diary confession, ‘Speak Now’ is altogether a more brash, “white-veil occasion” destroying fantasy.

Writing a version of this song as a 17-year-old could be understandable, but doing it in your twenties is harder to justify — even as a fantasy it reflects poorly on Swift. And the fact it’s the title of her third album only underlines the sentiment that she is willing to do literally anything for love — at least in her head.

But of course this snake precursor has aged worse than three-quarter pants, and that’s probably the reason she’s played it live only once in the last six years.


‘We Are Never Ever Getting Back Together’ (2012)

The looped guitar again shows Taylor evolving and adapting her musicianship for her audience. She knows how to play the country twang when she wants to, she knows how to craft a commercial-radio lick, hell I wouldn’t be surprised if she could write a grunge album if she wanted to.

The strength of her as a musician is her versatility and it’s rarely spoken of. To speak simply, here she’s aiming for a song that will stay on BREAK UP SONGZ or I H8 JAKE playlists for the next few decades, and she doesn’t miss her target.

This is producer Max Martin’s specialty, and with Swift in bubblegum pop God mode, there was really no stopping the song, which became the fastest selling single in digital history by a female artist. But most importantly, for a woman who stares inwards so often in her music, it has the most self-aware line in her oeuvre:

“I’m really gonna miss you picking fights
And me, falling for it screaming that I’m right
And you, would hide away and find your peace of mind
With some indie record that’s much cooler than mine”

This points not only the internalised misogyny of the music industry that she deals with to this day; where male artists can make sappy love and break up songs and be celebrated, but Taylor Swift does it better than most and doesn’t even get reviewed.

To add insult to injury, only months after ignoring the 10 million copies that 1989 sold, the anointed ones in the music press had the audacity to review a 1989 covers album by an overrated problematic narcissist. And then, a few years later they drop a retrospective, five album review-suite days out from an album release day in the most transparent play for likes the internet has seen.


‘I Knew You Were Trouble’ (2012)

Lyrically, we find Swift in her most comfortable scorned-woman position as she throws daggers at 125 bpm, but instantly this feels a little different. The perfectly tuned guitar with lusciously produced chords is replaced by stunted strumming that uses her guitar to augment the beat, and where we once had banjos, we now have a kick drum that sounds like it’s caving in your front door.

And this is our new pop star in full flight, favouring the mechanics of a hit song over traditional musicianship. She had nothing left to prove on that front anyway, but this showed that she could go a lot further than a four chord love song, experimenting by repeating the last syllable in a lyric to mimic a beat and double tracking her voice on the way to a motherfucking Skrillex-inspired dubstep drop.

It may seem old hat now, but in 2012, Taylor Swift doing a bass drop was fucking REVOLUTIONARY.


‘All Too Well’ (2012)

‘All Too Well’ is simply next level shit. Although that doesn’t even do it justice — ‘All Too Well’ is some Lucinda Williams shit. ‘All Too Well’ is storytelling. I wouldn’t be surprised if Gillian Welch had this song on a playlist for when she’s feeling particularly blue.

Framed within snapshots of a past romance (Jake Gyllenhaal, for those playing at home), there’s no anger in her voice, just a sadness at what could have been. It’s cinematic in its scope, with specific descriptions that paint vivid pictures of dancing in refrigerator lights. It also has a lyric that tops any break up manifesto she has ever written and it will probably never be bested:

“Maybe we got lost in translation, maybe I asked for too much,
And maybe this thing was a masterpiece until you tore it all up.
Running scared, I was there, I remember it all too well.
Then you call me up again just to break me like a promise.
So casually cruel in the name of being honest.
I’m a crumpled up piece of paper lying here
‘Cause I remember it all, all, all too well.”

Hey Jake, it’s time to give back the scarf.


‘Shake It Off ‘(2014)

I have a feeling even Taylor knows this song is as annoying as bedbugs in a bridal bed. But that’s its raison d’etre. She wrote it as a jingle like Audi selling a car, ‘Shake It Off’ was released to make sure you could not forget that 1989 was about to be the biggest pop album of the year.

The rap breakdown might be the whitest moment in music since MC Hammer, but no one knows it more than her — this is tongue-in-cheek marketing at its peak. She knows you will be humming this in the shower for the next three days and cursing her name under your breath, and she loves it.

Technically the song is about resilience and not letting people drag you down, but Tay Tay doesn’t really care whether you buy the message, as long as you get down to. this. sick. beat. Yeah, the radio playing it for the 500th time was annoying as fuck but for Team Taylor, that just smells like success and the haters gonna hate, hate, hate, hate, hate…


‘Blank Space’ (2014)

I can see why the conservative Texans weren’t happy with this one. Their wholesome, immaculate poster girl was now OPENLY REFERENCING SEXUAL INNUENDO! We’ve had Taylor in relationships before, but there was nothing to suggest they were not chaste and virginal. But how else do you make the bad guys good for a weekend?

This was Swift officially crossing the picket line, leaving country behind for a world of unadulterated pop stardom; filled with sparse hip-hop beats and provocative statements like “boys only want love if it’s torture”.

No one knows what she meant by Starbucks lovers but we all knew “a nightmare dressed as a daydream” did not belong at the American Country Music Awards. Not understanding that satire is really the only way a woman constantly besieged by paparazzi can comment on anything, this was in fact a woman revelling in her prescribed solipsism. The world called her a man-eater, so she wrote the best pop song of the year about chewing through men. Hall & Oates would be proud.


‘Style’ (2014)

‘Style’ is as much about fame as it is her relationship with former One Direction star Harry Styles. As someone who spent her transition from adolescence to adulthood in the public eye, there’s a hint of fascination in what they could have been. Referencing his James Dean look and painting herself in Marilyn Monroe imagery, it’s her only song that so obviously references a public relationship where she looks back with rose-coloured glasses.

It’s as if the song is less about him as a man than the romanticism of what they would’ve represented together. Even the use of the pronoun ‘we’ in the chorus is unlike any other song she’s written about an ex, and there’s an absence of antagonism that makes this an outlier in her discography.

With a Nile Rogers inspired guitar lick and an ’80s synth kicking the song along, it makes for a refreshing change of palette from the emotive gut punch of the rest of her ‘songs about exes’ collection.


‘Clean’ (2014)

It wasn’t even a single, but as far as her evolution goes as an artist, this was an understated leap in progression. Closing her masterpiece 1989, ‘Clean’ reframes love, heartache and all the bullshit in between as just steps in a larger journey of self-acceptance and happiness. The album might be called 1989 because it’s a woman finally mature enough to reflect on her youth with a critical lens.

And after four albums riding on her emotional rollercoaster, ‘Clean’ is a moment of calm, a welcome respite from her dizzying highs and tempestuous lows. You just wanna give her a hug. She’s finally found her zen and may it may it last forever…hang on, is that a Kim Kardashian Snapchat story? Shit.


‘Look What You Made Me Do’ (2017)

That first text you send after an argument is rarely a smart idea. And billed as her long awaited comeback to Kim and Kanye after they outed her for lying about her knowledge of ‘Famous’, the first single of reputation instead came across as a pathetic rehash of old news.

The controversy was almost 18 months old and it sadly it seemed the only one who still cared about it was Taylor. Now it’s important to note that if this song slayed, it wouldn’t matter if the feud was 18 months old or years old, but the timing became a factor because the song sucked.

It seems counterintuitive to describe a song of Taylor Swift’s as over-dramatic, but Jack Antonoff should’ve said no. Electro-clash hadn’t been cool for almost a decade and the bridge where she repeats the title of the song is just bad songwriting as well as blame dodging.

Instead of playing the victim, it would have been stronger to own the fuck up and bite back; instead there is a middle-eight breakdown where a voicemail Taylor Swift tell us “I’m sorry, the old Taylor can’t come to the phone right now…Why? Oh, ’cause she’s dead!”

So for those who thought the über-white faux-rapping in ‘Shake It Off’ was as cringe-worthy as Swift could get, check yo’ self.


‘Delicate’ (2017)

Out of all the songs on reputation that try to reframe her tumultuous preceding year, ‘Delicate’ nails the pathos the most effectively. Maybe she uses autotune to hide her voice as a metaphor for her cultural exile, but it’s more likely that she uses it because it makes a cool juxtaposition when her verse drops.

Either way the song succeeds for all the reasons ‘Look What You Made Me Do’ fails; it is at once inextricably linked to her fall from grace, but most importantly never addresses it. And as such, it’s humble without being self-pitying and sounds like someone just trying to move on with their life.

The line “my reputation has never been worse so you must like me for me” points to a larger insecurity that people fall in love with the idea of her brand and not her as a person. And this is crushing.

The confident swagger of 1989 is gone, and the entire chorus is her meekly asking questions of her new flame, underlining her self-doubt and unwittingly painting a far more sympathetic character than any fake bravado could conjure.


‘Call It What You Want’ (2017)

This is Taylor Swift at her most wounded and her most defenceless. Even symbolically she doesn’t have her guitar to deflect attention from her anymore. She tells us that she’s doing better than she ever was over a dime a dozen trip beat and barely sounds like she’s convincing herself.

This song is important for Swift because whether she likes it or not, it’s her admitting defeat of her narrative; call it what you want, she’s lost her power. She no longer has the currency to redirect through red herrings or satire, she’s exposed and for a woman who has lived in a house of mirrors for over a decade, this is her biggest fear.

Whether she likes it or not, it’s her admitting defeat of her narrative; call it what you want, she’s lost her power.

She sings of a man in the most vague of terms, he’s a saviour figure and that’s about all we get. He probably doesn’t exist — you can tell when Swift writes about a real man, because she could describe his nose hair over an E Chord if she wanted. She has never shied away from detail or drama; so this picture perfect, ambiguous Ken Doll is most likely a prop for her own emotional gestation.

It’s also noteworthy that she spends a lot the song berating herself for giving in to her greatest flaws and reflecting on a time where she regrettably lashed out. And for a woman who never takes a backwards step in a fight, this is the closest we’ve ever got to her telling us that she wished she knew how to. Humility is a virtue.


‘New Year’s Day’ (2017)

This song is interesting for its placement alone. The last track of reputation, an album that is spent largely airing Swift’s spiteful thoughts, ‘New Year’s Day’ is the sound of her turning over a new page. There’s no mention of betrayal or revenge, just her refreshing optimism at the beginning of a new relationship.

As a composition it sounds like it could be the prelude to ‘All Too Well’, with a simple piano juxtaposing the hyper-produced wall of sound Antonoff and Martin soaked the rest of the album in.

But symbolically, it shows that the IDGAF attitude of Side A1 was just a mask she needed to endure her public stoning, a cruel sport the public happily watched from the comfort of Instagram because hey, who doesn’t like a famous woman being roasted huh? But for Taylor, it’s the start of a new year and it’s only going to get better in a few months with the release of Kanye’s woeful album Ye.


‘You Need To Calm Down’ (2019)

The apolitical pop star finally shows her stripes. Yes, she had tweeted previously, but for a long time, the biggest pop star in the most political climate in the world was conspicuously silent. And it made sense.

The conventional — and not necessarily correct — wisdom was that the country Taylor couldn’t come out as a trans-supporting, queer-loving liberal without losing her base, as if she was an Alabaman Senator up for re-election. So ‘You Need To Calm Down’ is her answer to everyone, from the blue-belt liberals who have been screaming at her to take a position for years, to the Fox News hosts whose apoplectic reaction to the song justified its own existence.

It was released in a year with no midterms or general elections, specifically so she could not be accused of electioneering, yet Swift still feels the need to justify her own position: “And I ain’t tryna mess with your self-expression, but I’ve learned a lesson that stressin’ and obsessin’ ’bout somebody else is no fun.” A cute sentiment, but we are now living in a post-Trump world and despite her calls for amnesty, they will fall on deaf ears.

She even calls for an end to the pop star wars, hugging a giant burger version of Katy Perry (it makes a semblance of sense in the video) so if there’s one good thing to come from this call to action, it’s the end of that petulant hostility. There was never any need for bad blood anyway.


‘The Archer’ (2019)

In her spirit of constant reinvention, ‘The Archer’ is one of Taylor Swift’s biggest teases. The song’s structure is one long crescendo and ends two beats before the payoff and such restraint, despite not playing to our instinctive desire, it so damn unlike Swift as a songwriter that you have to admire it.

It’s a philosophical reclamation of the control she was so bereft of on reputation — and its brooding, building slow burn refuses to give you satisfaction you so dearly want. Singing contemplatively about her role on both sides of the residual drama, Jack Antonoff weaves his magic in an uncharacteristically understated way, turning a sombre and reflective moment from our antagonist in chief into a moment of clarity. It’s simply stunning.


‘Lover’ (2019)

Swift’s songwriting has always been its best when it feels like she’s talking directly to you; like she’s pulled you into the corner of a bar and she has something incredibly important to tell you. On ‘Lover’, she places her vocals high in the mix and leaves the country-throwback guitar to simply keep her tempo. It’s a nostalgic touch without it being overly produced or over wrought.

On the contrary, the song is as effortless that we’ve ever heard her, which is charming in itself as she recalls details that throw pictures in your mind so easily. The tightrope between her Nashville naivety and New York maturity has never been walked so delicately and it makes for a feeling that has been desperately rare in her recording career: Happiness.

The fact that her voice sounds so impossibly close to Hope Sandoval is the highest compliment one can pay her in under 4000 words, so we’ll leave it at that.


Chris Lewis is a writer and critic based in Melbourne. He is on Twitter