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. Nevertheless, we’re giving it a crack.

Here is Holler’s definitive list of the best Taylor Swift songs.

Taylor Swift

2021 | Sony

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.

Taylor Swift - Red (Deluxe Edition) - Album Cover

Big Machine Label Group | 2012


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.

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.

Taylor Swift - Reputation - Album Cover

Big Machine Records | 2017


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.

Taylor Swift - 1989 - Album Cover

Big Machine Records | 2014


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.

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

Taylor Swift | 2021


“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.

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.

Taylor Swift - Folklore - Album Cover

Taylor Swift | 2020


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.

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’.

Taylor Swift - Speak Now - Album Cover

Big Machine Records | 2010


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.

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.

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.

Taylor Swift - Folklore - Album Cover

Taylor Swift | 2020


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.

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.

Taylor Swift - Red (Deluxe Edition) - Album Cover

Big Machine Label Group | 2012

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.

Written again with Liz Rose, the song is commonly assumed to be about Jake Gyllenhaal, who Taylor dated briefly in 2010; a theory 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?’

Taylor Swift - Folklore - Album Cover

Taylor Swift | 2020


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.

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.

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".

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.

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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