Taylor Swift’s decades-long career has been nothing short of illustrious. Bursting onto the music scene at just 16 years old, the singer-songwriter has graduated from teen country sensation to international superstar, boasting an impressive discography of 15 albums (including four re-recorded ones) and counting. To celebrate her artistry and influence over the music world, we did the near impossible: we curated a list of her 20 best songs and ranked them from the good to the greatest of all time.

20. I Can Do It With a Broken Heart

Taylor Swift might have moved on from her country era, but the music from her eponymous debut album still lives on in the hearts of many. One of them is “Our Song”, which Swift had penned during her freshman year in high school for a talent show. It was born out of a realisation that the singer and her then-boyfriend lacked a song that they could call their own. The result is a joyful ditty that stands the test of time. The whimsical lyrics paired with the playful melody make it a true Swiftie fan favourite.

18. mirrorball

There’s something simply nostalgic and heartbreaking about this dainty, understated song on folklore. Maybe it’s the shimmering tambourine or the sentimental guitar that drifts through the song. Or maybe it’s the wistful scenes that Swift conjures that evoke such feelings. On “mirrorball”, the singer uses the fragile, splintered sphere as a metaphor to describe a person who constantly reshapes themselves to shine for others. They’re driven by a desire to bring joy but ultimately seek validation and tend to lose their real self in the process — a tireless routine Swift herself is guilty of. There’s vulnerability woven into the song that feels unlike anything else.

17. Back to December

Cover art of Swift’s third album, Speak Now

“Back to December”, which appears on her album Speak Now, is an ode to a former flame (many believe it to be actor Taylor Lautner). However, rather than opting for a sassy dismissal of the past romance, the song takes a more wistful approach. In this bittersweet and stinging reflection, Swift grapples with the regret of not fully appreciating what she had until it was lost. It’s a hard pill to swallow, but she acknowledges her mistake and extends a heartfelt apology for not treating her partner well during their time together. “Wishin’ I’d realised what I had when you were mine,” she laments. “I go back to December, turn around and change my own mind.”

16. Daylight

Quite fitting that one of Swift’s best love songs, “Daylight”, is from her album Lover

Love songs are at the core of Swift’s music, and “Daylight”, from her album Lover, happens to be one of her best ones. Co-produced with Jack Antonoff, the dreamy stunner is about finding someone special who illuminates your darkness and leads you out of it. Swift describes this affection as akin to waking up after “sleepin’ so long in a 20-year dark night”. The song is also a sign of the singer’s own maturity and growth when it comes to the matters of the heart. Her era of being in reckless love has drawn to a close. Now, she’s moving toward a new type of romance, finding solace in security and stability, where uncertainty once lingered. “I once believed love would be burnin’ red / But it’s golden.”

15. The Prophecy

Some of Swift’s best songs are clearly her sad songs, and nothing pierces the heart quite like “The Prophecy”. Claiming her title as the Tortured Poet seriously, the singer-songwriter channels her inner Shakespeare to craft a melancholic anthem for all the hopeless romantics like herself. It’s as poetic as it is gut-wrenching, as she desperately craves a soulmate, wishing to be loved and to be seen by someone. Every line hits harder than the next and becomes crushingly painful when Swift deduces she’s not one of the great, fearless women she considers herself to be but quite the opposite when it comes to love.

12. marjorie

evermore features the tear-jerker “marjorie”, Swift’s ode to her late grandmother

Melancholic songs are aplenty on evermore, but “marjorie” wins the title for best tear-jerker. Written as a love letter to her late maternal grandmother, Marjorie Finlay, the song recalls Swift’s earliest and fondest memories with the former opera singer. But the pop star also takes the time to express her regrets, articulating the profound sorrow that accompanies the loss of a grandparent at a young age. The song becomes hauntingly beautiful when a recording of Finlay’s ethereal vocals echoes through the final chorus, alongside her granddaughter’s crooning. Swift’s sincere emotions bring comfort to those who’ve also experienced a similar type of grief.

13. Fresh Out the Slammer

No other song in Swift’s discography matches the uniqueness of “Fresh Out the Slammer”. Sure, there are several experimental standouts in her long list of work (honorary mentions to evermore’s “closure” and Midnights’ “Labyrinth”, but this abstract moment on The Tortured Poets Department takes a different path and earns its place on this list). The song is simultaneously fresh yet familiar. It opens with a folksy twang before veering off course and abruptly switching to a different tempo. The song might sound incoherent, but on closer listen, its disjointedness is intentional and impressive. It proves that when Swift pairs her songwriting skills with her masterful production, her storytelling reaches greater heights.

12. New Romantics

“New Romantics” is a light-hearted stadium pop anthem about being young and carefree. On it, Swift lets go of the traditional definition of what it means to fall in love and welcomes a rebellious new outlook on the subject by proudly embracing heartbreak, the naysayers, the delusion, and unrealistic romantic expectations when it comes to relationships. It’s a fun and satirical take on romance — it acknowledges that sometimes being in love isn’t all sunshine and rainbows; sometimes it’s about being ‘left on read’. And that’s totally okay because we’ll just move on to the next person.

11. Wildest Dreams (Taylor’s Version)

Like any other young adult, Swift’s perception of romance changed as she grew older. As a teen, the singer viewed love as something idealistic with only happy endings in sight. Then she realised that love could also take on other forms, including passionate, fleeting affairs. What makes “Wildest Dreams” a true stunner is the fact that Swift had recorded the sound of her heartbeat, which was later mixed into the song by producers Max Martin and Shellback. The pulsating beat gives the track its dramatic opening, and it’s one of the highlights of her album, 1989. You could say that Swift really poured her whole heart into this one.

10. Cruel Summer

Swift perfected the formula for a certified pop hit with the sleek Lover standout, “Cruel Summer”. It’s got a catchy hook, clever lyrics, plus an infectious bass-heavy beat. What really makes the song a total smash, however, is the brilliant bridge. Sure, Swift has probably written stronger and better bridges elsewhere, but none can match the sheer intensity and candour found in the one featured in “Cruel Summer”. It’s over the top and slightly theatrical, but the lyrics encapsulate the sensation of falling deeply and irrevocably in love. And whenever the bridge comes on, you just can’t help but scream it out loud with her.

9. You Belong With Me

Cover art for Fearless

A list of Taylor Swift’s greatest hits wouldn’t be complete without this classic. Taken from her second studio album, Fearless, “You Belong With Me” was revealed as one of the last songs the singer had written for the album’s recording sessions. It features your typical teenage love story: shy girl likes cool guy, but guy is unfortunately unavailable. If only he knew the girl of his dreams was just next door. The premise is simple and straightforward, yet as the song’s banjo-driven melody crescendos toward the chorus, it becomes undeniably irresistible not to belt out and join in on the singing.

8. New Year’s Day

Cover art for Reputation

The stripped-down “New Year’s Day” is a surprisingly tender moment that closes out 2017’s Reputation, an album full of high-octane bangers and confident, bombastic pop production. Swift presents the sentimental ballad like an oath to her lover, promising them that she’ll still stick around even after the party, fireworks, and celebrations are long over. “Hold on to the memories, they will hold on to you,” she assures over gentle piano and guitar plucking, before softly vowing, “And I will hold on to you.” The vulnerability in Swift’s vocals here is as powerful as it is soul-crushing.

7. State of Grace

“State of Grace” is the perfect cinematic opening to Red. It marked a new beginning for Swift as an artist, signalling her transition away from country music to explore new sounds and expand her musical repertoire. With its pounding drums and steely guitars, the alternative rock cut was a breath of fresh air. On the song, Swift delivers one of her most poetic lines about a deep and passionate romance that went as quickly as it came: “So you were never a saint, and I loved in shades of wrong / We learn to live with the pain, mosaic broken hearts / But this love is brave and wild.”

6. August

On folklore, Swift moves away from her confessional lyrics to craft fictional characters and personas

On folklore, Taylor Swift crafted a fictional love triangle that was told through three songs: “cardigan”, “august”, and “betty”. Each track features a different perspective, with “august” narrated from the viewpoint of the other woman involved in the relationship. However, the song harbours no malice. Rather, it is about coming to the heartbreaking realisation that the feelings shared with another might or will never be reciprocated. “To live for the hope of it all / Cancel plans just in case you’d call,” she sighs. Unrequited love can be tough, but Swift has the knack for making it even more devastatingly painful.

5. Dear John

This guitar ballad from 2010’s Speak Now is arguably one of Swift’s most heart-tugging songs to come about. She was only 20 years old at the time it was released, but “Dear John” remains a remarkable display of what the singer-songwriter excels at: boldly showcasing her vulnerabilities. The fragility in her lyrics and the sadness in her vocals transform the song’s slow burn into a poignant portrayal of a destructive and harmful relationship. Over the song’s six-minute duration, the track gradually evolves from the depths of remorse and regret to reach a moment of empowering liberation.

4. You’re on Your Own, Kid

Cover art for Midnights, 2024’s Grammy Award Winner for Album of the Year

Swift’s Midnights is, in a nutshell, about self-reflection. Despite the bright pop music that runs through the album, the 13-track Grammy-winning record is a peek into the superstar’s innermost and intimate thoughts. She navigates her insecurities and failures with honesty while simultaneously learning how to heal herself from self-loathing. “You’re on Your Own, Kid”, the fifth track of the album, serves as a life lesson in fostering resilience when faced with challenges. “Everything you lose is a step you take,” she assures. The sprinkle of wisdom acts as a reminder not only to Swift’s fans but also to herself, as she continues to learn and grow throughout her life career.

3. The Last Great American Dynasty

Many have called Taylor Swift a master storyteller. And no other song in the pop star’s discography can attest to that claim as much as “The Last Great American Dynasty”, which she co-wrote with her folklore collaborator Aaron Dessner of The National. The song, which features a contemporary pop and indie-folk melody, paints a vivid story of the famous socialite who’d previously owned Swift’s pristine Rhode Island beach mansion. The track peaks once it shifts from a third-person narrative into Swift’s perspective, as she draws striking similarities between the two “mad” women who had a “marvellous time ruining everything”.

2. Style

Cover art of 1989 (Taylor’s Version)

Not all love affairs are made equal — some are just more memorable and iconic than others. When this song was first released in 2014, fans theorised that “Style” might be about Swift’s fleeting romance with former One Direction member Harry Styles, though it was never confirmed. Regardless of the rumours, one thing, however, is true: the song is an intoxicating pop masterpiece from start to finish. On it, Swift details a secret relationship between two individuals who continuously find themselves inexorably drawn to each other, despite their efforts to break apart. Maybe it’s his James Dean-esque charm, or perhaps it’s the bold crimson hue of her lipstick. Whatever the allure may be, they make a timeless pair.

1. All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault)

Cover art of Red