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The Best Taylor Swift Songs

By Jof Owen

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Before Taylor Swift came along, country music was primarily music made by adults, for adults and about adults. Tanya Tucker and LeAnn Rimes might not have turned 16 yet when they broke through, but their songs touched on the same adult themes that country always had.

That all changed with Swift; she was singing from the perspective of a teenager. There’s a stamp on the country music timeline that distinctly recognises the Swiftian era – both before and after – because once she arrived, everything changed.

It would be difficult to narrow down a definitive list of top songs for a lot of artists, but with Taylor, it’s damn near impossible. Now, with the release of Midnights, it's even harder. Nevertheless, we’re giving it a crack.

Here is Holler’s definitive list of the best Taylor Swift songs, from her self-titled debut to Midnights.

Taylor Swift

2021 | Sony

30
Taylor Swift - Red (Deluxe Edition) - Album Cover

Big Machine Label Group | 2012

We Are Never Ever Getting Back Together

Maybe it’s the reiterated “Ever” in the song’s title or the savage spoken-word middle eight -“Ugh, so he calls me up and he’s like, “I still love you” / And I’m like… I mean, this is exhausting, you know? / Like, we are never getting back together… like, ever”.

There’s something about this snarky eye-roller that manages to bring together everything that anyone who has ever loved Taylor Swift loves into one three-minute pop masterpiece.

One of three songs off Red written with Max Martin and Shellback, it’s unmistakeably Taylor: a hilarious and self-deprecating break-up song delivered with a relatable girl-next-door charm and a chorus that literally explodes across the dancefloor.

It was 2012, and without knowing it, Taylor Swift was about to take over pop culture for the foreseeable future. This was the moment when it all began to get massive.

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Taylor Swift - Taylor Swift - Album Cover

Big Machine Records | 2008

Tim McGraw

25 years ago, Taylor Swift was sitting in her freshman year maths class when the inspiration for ‘Tim McGraw’ struck. Knowing that she and her current boyfriend – a senior at the time - would break up at the end of the year when he left for college, she began daydreaming about all the different things that might remind him of her and the time they spent together.

She began humming the melody in her head and took it to her co-writer Liz Rose after school; they finished it off at a piano in 20 minutes. It became her first single and the opening track on her debut album. Sadly, McGraw himself has never returned the gesture and wrote a song called ‘Taylor Swift’. Well, not as far as we know anyway.

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Taylor Swift

2021 | Sony

Better Man

Just when the whole world was wondering if Taylor would ever go back to her country roots she proved to them all she still had her country chops when she gifted this exquisite mid-tempo country ballad to Little Big Town for their 2017 album The Breaker.

Karen Fairchild's vocal was as perfect as we could have hoped for, but it was still a delight for us all when Taylor cut a version herself for the vault tracks of Red (Taylor's Version)

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Taylor Swift - Red (Deluxe Edition) - Album Cover

Big Machine Label Group | 2012

22

Swift came up with a birthday anthem for twenty-two-year-olds everywhere with this carefree bubble-gum country banger about staying up all night, making fun of your exes and having breakfast at midnight.

“We're happy, free, confused and lonely at the same time, it's miserable and magical” Taylor sang, summing up her early twenties and signalling the full-on pivot into pop that was to come.

Famously including the bitchy aside “Who's Taylor Swift anyway? Ew”, no one would be asking that now.

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Taylor Swift - Lover - Album Cover

Taylor Swift | 2019

Soon You’ll Get Better

Nestled in amongst all the summery pop froth of Taylor’s seventh album, Lover, was this sparsely orchestrated country lullaby and one of the most personal songs Taylor has ever written.

Featuring The Chicks on backing vocals, she wrote it about the battles that both of her parents have had with cancer, after her mother, Andrea, had been diagnosed with a brain tumour.

“It's something I'm so proud of. I can't sing it. It's hard to emotionally deal with that song", she said about the song when it came out.

She would perform it a year later, sitting solo at a piano for the One World: Together At Home live stream, where it became one of the most poignant pop culture moments of the pandemic.

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Taylor Swift - Reputation - Album Cover

Big Machine Records | 2017

Dress

Towards the backend of Taylor’s Reputation album, she took a break from taking swipes at her nemeses with this sultry pop gem, the chorus a pickup line in itself.

“Carve your name into my bedpost ‘cause I don't want you like a best friend / Only bought this dress so you could take it off”, Taylor sings breathlessly, steaming up the mirrors and spilling wine in the bathtub.

When the song came out, speculation between Swifties was divided over who the best friend in the song was: Ed Sheeran or Karlie Kloss.

Turns out it was probably neither. References to a “buzzcut” and bleached blonde hair are more likely to be to when she first met future boyfriend Joe Alwyn at the Met Gala in 2016.

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Taylor Swift - 1989 - Album Cover

Big Machine Records | 2014

Style

No need to speculate on who the third single from Taylor’s 1989 album was about.

The lyrics - written about a couple in an unhealthy relationship from which they couldn’t disentangle themselves - were full of clues to late-night drives, lipstick shades and long slicked-back hair.

Taylor finally put an end to fifteen years of Reddit posts when she confirmed the song was written about ex-boyfriend Harry Styles in an interview with Rolling Stone in 2014.

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Taylor Swift

2021 | Sony

I Bet You Think About Me (featuring Chris Stapleton)

If 'Better Man' wasn't enough of a country treat for Taylor fans this duet with country heavyweight Chris Stapleton was enough to send them into an absolute conniption fit.

This brutal no holds barred rebuttal to an ex-lover was full of juicy takedowns like "Mr Superior Thinking, do you have all the space that you need?" and hilarious one liners about soul searching, "cool indie music concerts" and organic shoes and a "million dollar couch".

The song was written with Lori McKenna and the music video was directed by the actress Blake Lively, which sees Swift crashing an ex's big wedding day.

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Taylor Swift - Fearless (Taylor's Version) - Album Cover

Taylor Swift | 2021

Fifteen

“In your life you'll do things greater than dating the boy on the football team, but I didn't know it at fifteen”, sings Taylor on the fourth single from Fearless.

A true-to-life tale of high school heartbreak, it was inspired by Swift's first freshman year at Hendersonville High School, where she says she had her heartbroken for the first time, along with her best friend Abigail Anderson.

The song, which doubles up as a cautionary tale for teenage girls, was so personal to Taylor that she cried when she was recording it, admitting that it still gets to her all these years later when she performs it live.

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Taylor Swift - Red (Deluxe Edition) - Album Cover

Big Machine Label Group | 2012

Begin Again

The closing song on Red found Taylor returning momentarily to her country roots for one last look around; all before she went off into the world of pop forever.

As Taylor describes it, it’s a song "about when you've gotten through a really bad relationship, you finally dust yourself off and go on that first date after - and all the vulnerability that goes along with that".

In the video, Taylor is seen riding a bicycle along the cobbled streets of Paris; shopping for clothes, sipping cappuccinos in Parisian cafés and generally living her best life.

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Taylor Swift - Folklore - Album Cover

Taylor Swift | 2020

cardigan

While we were all baking banana bread and doing Joe Wicks workouts, Taylor was busy spending the first COVID lockdown completely reinventing herself.

She spent it recording not one but TWO new albums (as well as rerecording a third), with The National’s Aaron Dessner at the helm.

Written with Dessner, ‘cardigan’ was the lead single from Folklore; a slow-burning indie ballad about young love and lost innocence.

It was told from the perspective of a female narrator called Betty, one of several fictional characters that the Swiftiverse was about to become very familiar with.

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Taylor Swift - Reputation - Album Cover

Big Machine Records | 2017

New Year's Day

It’s the day after the high drama house party that was Reputation, as the album closes out and Taylor is left to clean up the absolute mess from the night before.

Written after a party at her London home, the delicate piano ballad gave us a moment’s pause to reflect at the end of the album, signposting less stormy waters ahead.

"I was thinking about how everybody talks and thinks about who you kiss at midnight”, Taylor explained about the song’s origins. “But I think there's something even more romantic about who's gonna deal with you on New Year's Day. Who's willing to give you Advil and clean up the house? I think that states more of a permanence”.

Olivia Rodrigo would go on to interpolate the piano chords for her song ‘1 Step Forward, 3 Steps Back’.

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Taylor Swift - Speak Now - Album Cover

Big Machine Records | 2010

Mean

Speak Now is the only one of Taylor’s albums where all the songs were written solely by her, and this poppy little bluegrass takedown found her squaring up to her detractors.

Purportedly inspired by a review the infamous blogger Bob Lefsetz had written of Taylor’s “off-key” performance with Stevie Nicks at the Grammys in 2010, Taylor got her revenge when the song picked up a pair of Grammys two years later.

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Taylor Swift - 1989 - Album Cover

Big Machine Records | 2014

Shake It Off

The haters kept on hating though. Taylor was still brushing them off a few years later when she dropped the country elements from her sound altogether, going full-on pop with 1989.

Amidst the album’s 80s synth-pop sophistication was this Toni Basil-esque cheerleader chant. If Red had increased Taylor’s mainstream visibility, ‘Shake It Off’ was the moment when she became so big you could see her from space.

The song became such a pop culture phenomenon that the phrase "this sick beat" was trademarked to Swift by the US Patent and Trademark Office.

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Holler Country Music

Taylor Swift | 2021

Wildest Dreams (Taylor's Version)

Taylor's always been a dreamer and when it comes to the relationships she sings about in her songs she's been known to let her heart get carried away and often ends up wit a broken heart because of it.

'Wildest Dreams' is Taylor in full on fatalist mode, already racing to the end of the relationship before it's barely even begun.

"I think the way I used to approach relationships was very idealistic," she admitted to Rolling Stone. "I used to go into them thinking, 'Maybe this is the one - we'll get married and have a family, this could be forever. Whereas now I go in thinking, 'How long do we have on the clock - before something comes along and puts a wrench in it, or your publicist calls and says this isn't a good idea?"

Taylor gave a personal touch to the percussion on the track by adding a recording of her heartbeat thumping throughout the song.

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Holler Country Music

Taylor Swift | 2022

You're On Your Own, Kid

Every Swifty knows that when you get to track five on any Taylor Swift record shit is about to get real. On Midnights track five is 'You're On Your Own, Kid,' and it's probably the most real Taylor has ever got.

One of Taylor’s greatest ever break up songs, and she's written a few of those! It’s got echoes of ‘Getaway Car’ but this time she’s all alone, escaping her own struggles with success and her own mental health. Like all the best Taylor songs it's intimate and deeply personal but also completely universal and relatable to anyone going through dark times.

At one point she even alludes to the eating disorder she previously spoke about in her Miss Americana film in the lyrics "From sprinkler splashes to fireplace ashes / I gave my blood, sweat and tears for this / I hosted parties and starved my body / Like I'd be saved by a perfect kiss."

A fan favourite as soon as they got to it at 15 minutes past midnight.

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Taylor Swift - Red (Deluxe Edition) - Album Cover

Big Machine Label Group | 2012

I Knew You Were Trouble

Even before 1989, Taylor was getting inspiration from her failed romance with Harry Styles.

After a feisty performance of this song at the Brits in 2013 – where Styles was in the audience - she admitted that it wasn’t “hard to access that emotion when the person the song is directed at is standing side of the stage watching”.

Written with Max Martin and Shellback, ‘I Knew You Were Trouble’ was Taylor mixing the stadium-sized country-pop of Shania with the all-out pop of Britney to devastating effect, even managing to mix a little dubstep into the song’s refrain.

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Taylor Swift - Folklore - Album Cover

Taylor Swift | 2020

betty

Mysteriously credited to Swift and William Bowery when Folklore first came out, Taylor later revealed that it was in fact co-written with her boyfriend Joe Alwyn, after she heard him "singing the entire, fully formed chorus from another room".

With its harpsichord, harmonica and Freewheelin’ feel, ‘betty’ was Taylor’s most out and out country song for some time.

Here, she returned to the love triangle of ‘cardigan’, this time from the point of view of James, “a seventeen-year-old standing on a porch learning to apologise”.

Swift cited Patty Griffin’s ‘Top of The World’ as her inspiration to write from a male perspective.

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Taylor Swift - Fearless (Taylor's Version) - Album Cover

Taylor Swift | 2021

You Belong With Me

Careful how close you stand to Taylor Swift when you’re on the phone, you might end up in a song.

This girl-next-door anthem from 2009 was inspired by a phone call that Taylor overheard between a male friend of hers and his girlfriend. Written with Liz Rose, they developed a storyline where Taylor is secretly in love with her friend, hoping he’ll break up with his current girlfriend so Taylor and him can get together.

The video, in which Taylor stars in dual roles as the short skirt wearing protagonist and the T-shirt wearing antagonist, won Best Female Video at the 2009 MTV awards. It was here that Kanye West famously stormed the stage during Taylor’s acceptance speech - protesting her win in support of Beyoncé.

It started the decade long feud between Taylor and West and the snake emoji would never be the same again.

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Taylor Swift - Folklore - Album Cover

Taylor Swift | 2020

august

The love triangle of Folklore is completed with ‘august’, as the unnamed third party picks up James and Betty’s story in this dreamy evocation of Summer longing and unrequited love.

The closest thing on the album to an out-and-out pop song, she performed it at the 63rd Annual Grammy Awards show, before walking off with the Album of The Year award.

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Taylor Swift - 1989 - Album Cover

Big Machine Records | 2014

Blank Space

Taylor’s got a lot of bangers in her pop closet, but this dramatic electro-pop gem from 1989 is hanging up there with the best of them.

"Got a long list of ex-lovers / They'll tell you I'm insane”, she sang in this satirical and knowingly self-referential nod to the media perception of her dating life and relationships. 

Absolutely nothing to do with Starbucks lovers then.

9
Holler Country Music

Taylor Swift | 2022

Maroon

Loving you was red, la la la la la! For Taylor red was always the colour of a deep passionate fiery love, but what about maroon? Which is a shade of red.

In this standout track from Midnights Swift describes a love affair that was "so scarlet it was maroon." The burgundy shade is the colour of the wine splashed on her T-shirt, the blood rushing to her cheeks and lots of other little details of a love affair that began with a man she was dancing with in New York with no shoes on.

She goes from singing "I chose you" in the first chorus to "I lost you" in the second the word and now Tom Hiddleston will forever be googled with the word "maroon".

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Taylor Swift - Lover - Album Cover

Taylor Swift | 2019

The Man

This incendiary take-down of society’s sexist double standards from the Lover album saw Taylor turning a corner into a more politically conscious stage of her career.

Upturning the tables on the media’s perception of her, she wondered how different those perceptions would be if she was male.

The video, directed by Taylor herself, sees her acting the role of her male alter-ego "Tyler Swift".

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Taylor Swift - Fearless (Taylor's Version) - Album Cover

Taylor Swift | 2021

Love Story

Written in just twenty minutes while sitting on her bedroom floor, ‘Love Story’ became one of Taylor’s biggest hits and remains one of her most enduring songs.

Shakespeare meets country-pop in this high school rewrite of Romeo and Juliet. While nothing ever came of the star-crossed fairy-tale relationship that inspired Taylor to write the song, the same relationship did also inspire ‘White Horse’ from the same album.

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Holler Country Music

Taylor Swift | 2022

Champagne Problems

Taylor has always been on point when it comes to college romances and the twists and turns of young love, and in this song off Evermore - written with Joe Alwyn under the alias William Bowery - she tells the story of two college sweethearts on the night that the boy plans to propose.

The girl in the song, having a change of heart, walks away from her lover on the night he planned to ask her to marry him, leaving him brokenhearted with his mother's ring in his pocket.

"Champagne problems" are easy problems that you don't have to worry about. Try telling that to the boy with a broken heart and a ring in his pocket.

5
Taylor Swift

2021 | Sony

Nothing New (featuring Phoebe Bridgers)

"Lord what will become of me once I've lost my novelty?" Taylor wonders aloud in this bonus track off Red (Taylor's Version). "How can a person know everything at 18 but nothing at 22?"

It's unimaginable to think of a situation where this was left off the original Red album and part of us will never completly forgive Taylor for keeping it from us all those years, but thankfully Taylor goes a long way towards making up for it by inviting Phoebe Bridgers in to sing on it.

With forlornly sung lyrics like "How long will it be cute, all this crying in my room, when you can't blame it on my youth" it's a blasting take down of the sexism young female pop stars often experience in the music industry.

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Taylor Swift - Folklore - Album Cover

Taylor Swift | 2020

The Last Great American Dynasty

In 2013, Taylor Swift purchased a waterfront mansion known as the "Holiday House" in the affluent Rhode Island village of Watch Hill for around $17 million. On this gorgeously melodic slow burner off Folklore Taylor imagines the sort of life the house might have witnessed when it was occupied by its previous owner, the eccentric heiress Rebekah Harkness.

"As soon as I found out about her, I wanted to know everything I could", Taylor explained. "So I started reading. I found her so interesting. And then as more parallels began to develop between our two lives - being the lady that lives in that house on the hill that everybody gets to gossip about - I was always looking for an opportunity to write about her. And I finally found it."

In the song's denouement Taylor switches it all into the first person and changes the line to "I had a marvelous time ruining everything".

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Taylor Swift - Lover - Album Cover

Taylor Swift | 2019

Lover

"We wanted to make music that could've been played on a wedding reception stage in 1970," Swift said of the title track to her 2019 album. It was produced entirely at New York City's Electric Lady Studios with only Taylor and sound engineer Laura Sisk in the room when she recorded it.

This cheeky little waltz is another soul baring confessional from Taylor but this time it's the super cute tiny everyday details of being comfortable in a relationship that she focuses in on. Leaving the Christmas lights up until January, saving each other a seat and just occupying the same little space on earth every day with someone you love.

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Holler Country Music

Taylor Swift | 2022

Anti-Hero

The lead single off Midnights proved she hadn't lost any of her knack for writing out-and-out pop bangers after the downbeat indietronica of Folkore and Evermore. It's a darkly comic late night confessional which Taylor has described as one of her favourite songs she's ever written.

"This song is a real guided tour throughout all the things that I tend to hate about myself," she said of the song. "We all hate things about ourselves, and it's all of those aspects of the things we dislike and like about ourselves that we have to come to terms with if we're going to be this person. So, yeah, I like 'Anti-Hero' a lot because I think it's really honest."

"I really don't think I've delved this far into my insecurities in this detail before," she added. "You know, I struggle a lot with the idea that my life has become unmanageably sized, and that I, you know… not to sound too dark, but I struggle with the idea of not feeling like a person. But don't feel bad for me. You don't need to."

1
Taylor Swift

2021 | Sony

All Too Well

A firm fan-favourite and the song from Red that Taylor has always described as being the hardest to write, this heart-wrenching break-up ballad finally came to her after a six-month writing block that followed a particularly painful ending to a relationship. Then when Taylor remade Red (Taylor's Version) she treated us all to a 10 minute version with lots of juicy new lyrics about lame key rings and awful dinner parties as well as an accompanying film starring Sadie Sink! OMG!

Written again with Liz Rose, the song is commonly assumed to be (it definitely is) about Jake Gyllenhaal, who Taylor dated briefly in 2010; a theory (fact) that Swifties jump on every chance they get.

When Gyllenhaal posted a childhood photo of himself wearing glasses in September 2020, his Instagram feed was flooded with Taylor Swift fans posting lyrics from ‘All Too Well’ in the comments.

The theory is so widespread that even Jake Gyllenhaal’s sister, Maggie, has had to answer questions about whether she still has Taylor’s scarf in a drawer at her house. “I never understood why everybody asked me about this scarf. What is this?” she said, when Andy Cohen asked Maggie about the scarf on Watch What Happens Live.

“I am in the dark about this scarf. It's totally possible it's there. I don't know. I have been asked this before, and I am like, ‘What are you talking about?’

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