1. ‘Our Song’ from Taylor Swift (2006)

Originally written for her high-school talent show on acoustic guitar, ‘Our Song’ became a setlist staple and fan favourite. With its bluegrass sensibilities, the track envisions an idyllic America where screen doors slam behind god-fearing families and young lovers, who keep their late-night calls under wraps “‘cause it’s late, and your mama don’t know”. The new couple struggle to find a ‘song’ befitting their relationship. So the tune ends with her grabbing a pen “and an old napkin” to write one herself. Alongside the romantic sentiments, the tune also finds Swift expressing her own artistic agency. Yes, it’s a treacly love song, but at its core, ‘Our Song’ tells the origin story of Taylor Swift.

2. ‘All Too Well’ (10 Minute Version) (From the Vault) from Red (Taylor’s Version) (2021)

For nearly a decade, fans and critics alike have placed ‘All Too Well’ in a league of its own, with many deeming it Swift’s best track. The singer had mentioned in an earlier interview that she originally wrote a 10-minute version before editing it down to the demo on 2012’s Red. Ever since, fans eagerly anticipated the moment the extended version would see release. Such an opportunity arose when Swift announced she would be re-recording Red, after a years-long battle to reclaim her masters. The extended ‘All Too Well’ went on to break the Guinness World Record for the longest song to top the Billboard Hot 100 (besting Don McClean’s ‘American Pie’), and its cinematic music video All Too Well: The Short Film continued to stretch the Swift multiverse. With candid lyricism, narrative catharsis and heartrending melodies, ‘All Too Well (10 Minute Version)’ contains everything that makes Swift a superstar.

3. ‘Love Story’ from Fearless (Taylor’s Version) (2021)

On her sophomore album Fearless, initially released in 2008 and re-recorded in 2021, Taylor takes on more pop sensibilities, looking to transition from her country roots. It’s a natural step, following the success of her self-titled LP and singles which vaulted up the charts two years prior.  Inspired by the tragic romance between Romeo and Juliet, ‘Love Story’ narrates a complicated relationship, softening the original Shakespearean ending with a surprise marriage proposal. With gleaming production and a more emphatic vocal delivery, the lyrics maintain the starry- eyed image of girlhood, but with the newfound disillusionments of growing up: heartbreak, anxieties and self-esteem issues. Still, as the album title suggests, there’s an underlying sense of liberation in the face of uncertainty.

4.‘Champagne Problems’ from Evermore (2021)

Confessional lyricism has long been Taylor’s superpower, and ‘Champagne Problems’ is no exception. The songstress navigates the ashes of a relationship after rejecting a marriage proposal. Here, she approaches songwriting as a blank slate, her thoughts spilling into the margins, using every open space to describe the creaking floors of a cabin, the fog on the windshield, the fingerprints on the car door. During the Evermore era, Taylor struck a folksier chord, enlisting the likes of Aaron Dessner and Bon Iver to see the vision through. Over a stripped-back piano arrangement, Taylor’s vocals waver between delicate and blunt, but always with fully-fledged artistry.

5. ‘Delicate’ from Reputation (2017)

There’s a new-found complexity to Swift’s sound on‘Delicate’: it’s catchy and lived in, with a brooding darkness lingering beneath the emotional hardwood. The brooding atmosphere suggests tension between her public and private lives, as she croons, “My reputation’s never been worse / So, you must like me for me”. It’s a love song disguised as the artist’s declaration of selfhood. But you don’t need to hear Taylor declare her old self dead to know that Reputation is both a warning shot aimed at her critics and a fully-fledged creative evolution. On ‘Delicate’, she accepts the vulnerability that accompanies such hard-won growth.

6. ‘You Belong With Me’ from Fearless (Taylor’s Version) (2021)

‘You Belong With Me’ has been one of Swift’s signature songs since it first debuted in 2008. The girl-next-door anthem was inspired by an overheard phone call between her band member and his girlfriend. Swift enlisted Liz Rose to help craft the storyline: the archetypal nerdy girl and the school’s football star exchange written messages at their windows, hoping he’ll break-up with his antagonistic cheerleader girlfriend. Merging country and pop, ‘You Belong With Me’ became a chart-topping crossover hit, certified seven times platinum. In the music video, Taylor stars as both girls, as they compete for the athlete’s affections. Many will remember when Swift won a VMA for the clip, prompting an interruption from Kanye West who believed Beyoncé deserved it. Thus began the ceaseless feud between West and Swift, cited in many of her future ‘diss’ tracks.

7. ‘Anti-Hero’ from Midnights (2022)

With her longest-running No. 1 hit ‘Anti-Hero’, Taylor coined the unforgettable phrase of 2022: “It’s me, hi! I’m the problem, it’s me”. The song delves deep into the artist’s own neuroses — on what she deemed a “guided tour” of insecurities — and how she contributes to them. Teaming up with trusted collaborator Jack Antonoff, ‘Anti-Hero’ features a methodical drum loop and scintillating synths to spotlight the lyrics: a series of vignettes detailing the singer’s past mistakes. With the tongue-in-cheek acknowledgment of her notoriety, the track brings a certain barbed levity to her own self-mythologising: “It must be exhausting always rooting for the anti-hero.”

8. ‘I Knew You Were Trouble’ from Red (Taylor’s Version) (2021)

With its initial release in 2012, ‘I Knew You Were Trouble’ marked a huge sonic leap which saw Swift experimenting with more electronic stylings. Though focusing on the now-familiar break-up themes, ‘I Knew You Were Trouble’ sounded like nothing she’d made before, with its dubstep refrain and propulsive hard-rock riffs. At first, it divided her country-pop audience. But today, it’s a rare EDM-pop crossover that’s stood the test of time, and also foreshadowed the electronic crossover of 2018’s Reputation.

9. ‘Shake It Off’ from 1989 (Taylor’s Version) (2023)

Before Taylor Swift released ‘Shake It Off’ - the lead single from her record-shattering 1989 - she flirted with full embrace of pop, following the acclaim for Red. It was a gutsy change that would either damage her career or catapult it to new heights. She took the leap anyway, despite the disapproval of many.   Her response? “Players gonna play” and “haters gonna hate”, so you might as well “shake it off”. The pop anthem directly addressed the detractors and constant media scrutiny hurled at her. As she opened her new era on 1989, Swift grew from the country-pop girl-next-door into something else entirely: a highly bankable superstar with homespun relatability, the ‘accidental’, and sometimes unwilling, idol.

10. ‘You’re On Your Own, Kid’ from Midnights (2022)

Almost any Swiftie worth their salt knows that when you get to track five on essentially any Taylor Swift record, it’s about to get real. If one word could sum up the fifth track off Midnights, it would be just that: real. ‘You’re On Your Own Kid’ centres on a young person longing for love, whilst  coming to the cruel realisation that life is a solo journey after all. It’s one of the most cathartic break-up anthems from Swift, which also includes one of her greatest bridges. “From sprinkler splashes to fireplace ashes,” the track explores the everyday moments of a relationship, the very things you give your “blood, sweat and tears for”. At the end of the day, however, “You’re on your own, kid. You always have been”.

11. ‘Blank Space’ from 1989 (Taylor’s Version) (2023)

Swift hoped to counter her persona as a ‘serial dater’ when she first dropped ‘Blank Space,’ a scintillating electro-pop gem from her fifth album 1989. It was biting and satirical in its self-awareness, a referential nod to the media’s portrayal of the popstar as a clingy, psychotic girlfriend who deflects any and all blame to the man when their relationship goes south. “Got a long list of ex-lovers, they’ll tell you I’m insane,” Taylor sings with newfound confidence and casually wry vengeance, poking fun at her detractors over bubblegum hooks and a hip- hop heartbeat.

12. ‘Betty’ from Folklore (2020)

‘Betty’ is a very Taylor Swift song: the recreational strumming of guitars, the obsession with young love, the weaving of a folktale. It’s a nod to Swift’s earlier country roots, on an album that’s anything but, a sliver of the old artist on a record that refutes old formulas. With its DIY production, the track discusses a love triangle over brazen strumming, pedal steel guitars and plaintive harmonica.

13. ‘Cruel Summer’ from Lover (2019)

When Taylor originally released Lover, the upbeat synth-pop tune ‘Cruel Summer’ became an immediate fan-favourite. And yet, it wasn’t released as a single until June 2023. The surprise re-release resulted from a resurgence in popularity on TikTok and other social media platforms, after Swift embarked on her record-smashing Eras Tour. Infectious and anthemic, its belated hit status is richly deserved.