Taylor Swift’s 20 best songs ranked

Taylor Swift has compiled an impressive catalog of hits and deep cuts. When she’s not singing about an ex, she’s lighting up the media for its constant obsession with her. Here, we’ve broken down her 20 best career highs.

Taylor Swift is a one-in-a-generation songwriter. In her 18-year career, she’s earned her place among the Mount Rushmore of songwriters, which includes folks like Joni Mitchell and Bob Dylan.

There’s something in the way she bends images to her will while relating those to the listener in a deeply probing way. You didn’t have to be there; Swift will write in such vivid detail that makes you believe you were.

Across 11 studio albums, Swift has conquered country, folk, and pop music, while also having dabbled in rock. Along the way, she’s enchanted with gripping fairytales and heart-weary confessions. Her songbook is impressive, so we had our work cut out for ourselves in selecting her 20 best songs. Here is our ranking.

20. ‘Our Song’

When ‘Our Song’ was released, the music industry went nuts. Here was a teenager writing in great detail about young love, indicating she was wise beyond her years, and destroying the game with each pen stroke.

With its jaunty melody and country refraction, ‘Our Song’ planted a flag in a business so adverse against letting women through the door. But Swift blew it down and stomped all over it, and she didn’t look back.

19. ‘Safe & Sound’ featuring Joy Williams & John Paul White

The now-separated Civil Wars (comprised of Joy Williams and John Paul White) were an unlikely match with Swift in her earlier days. With ‘Safe & Sound,’ a truly eerie performance, the trio carves a story inspired by The Hunger Games.

Percussion thumps like a heartbeat, giving the performances a tortured quality. “Just close your eyes / You’ll be alright,” Swift whispers into the darkness. With a Southern gothic coating, the song will rattle you to your core.

18. ‘august’

“You were never mine,” Swift reflects. She looks back upon an ill-fated summer fling, one packed full of memories she’ll cherish for the rest of her life. Guitar croaks behind her sterling vocal, almost as sun-kissed as the August heat.

17. ‘Teardrops on My Guitar’

Swift eyes Drew in the hallway, desperately wanting to be his girlfriend. As they’re good friends, Drew shares his feelings over a burgeoning romance with another girl. It crushes Swift, who turns to her guitar as a way to self-soothe and on which to write a new song. Unrequited love can certainly be painful.

The wistfulness seeps from every corner of the song, mirrored in both Swift’s heart-torn vocal and the string-laden instruments that seem to palpably ache and swell.

Even in those early days, Swift could turn a phrase and deliver a solid vocal performance. She packs in just enough emotion to make you care.

16. ‘Mean’

‘Mean’ is a very specific song lobbied at one music critic, in particular. Journalist Bob Lefsetz gave Swift a scathing review following a 2010 performance with Stevie Nicks, and it didn’t sit well with most fans. In retaliation, Swift wrote ‘Mean’ as a way to reclaim her agency and fire off a warning shot. Even in 2024, it’s a fiery little number that works well under any situation. It just has that effect on you.

15. ‘You Belong with Me’

‘You Belong with Me’ finds the listener rooting for the underdog. While Swift sits on the bleachers in her sneakers, the other girl is a cheerleader and the object of affection.

“What you’re looking for has been here the whole time!” she sings in the pre-chorus. Deep in her Fearless days, the jangly tune perfectly blends country with pop. And it was loud and clear that she was stretching her wings so she could one day fly the coop.

14. ‘Cornelia Street’

‘Cornelia Street’ shimmers underneath Taylor Swift’s unwavering gaze. The streets that lined a relationship’s early days have become seared upon her brain. When the relationship crashed, and it hit hard, she stumbles away from a love forever changed. “I’ll never walk Cornelia Street again,” she professes.

Drums crack like thunder, accents to her lead vocal that twists and bends with the production. As things oscillate from crunchiness to heart palpitations, you get the sense that that relationship was one for the ages, even if it did burn out in the end.

13. ‘my tears ricochet’

What makes folklore an important benchmark in Swift’s career is her ability to stage narratives outside of her personal experience. ‘my tears ricochet’ is a prime example. Detailing how a tormented lover returns to the grave of his dead lover, the prickly ballad ebbs and flows with the cascade of tears that shake loose from her eyes. It’s a subdued performance, but powerful nonetheless.

12. ‘no body, no crime’ featuring HAIM

Leave it to Taylor Swift to write a mysterious murder ballad out of nowhere. From evermore, ‘no body, no crime,’ assisted by HAIM, tells the tale of a murderous husband who just might have killed his wife, eventually bringing his mistress into his wedding bed.

“I ain’t letting up till the day I die,” sings Swift, convinced the husband did it. But as the song progresses, the layers crack and crumble to reveal the truth buried deep beneath its musical layers.

11. ‘Love Story’

‘Love Story’ crashed through pop culture in 2008 and left an undeniable bruise. As Swift’s pop crossover moment, it set her up for a long career. Not only does it carry the country storytelling tingle, but it allows the singer to expand her range and draw upon a delicious pop hook for good measure.

Swift fashions the classic Romeo & Juliet tale, which also references The Scarlet Letter, as one of true love finally connecting. It’s far from tragic, yet contains the beauty of eternally burning love.

“This love is difficult, but it’s real,” she admits. Such lines take the song into the stratosphere, giving it a theatrical edge you don’t hear on the rest of Fearless.

10. ‘Delicate’

Swift admits her “reputation’s never been worse” through a glittering vocal distortion. With ‘Delicate,’ she pulls a potential new lover closer and concedes that they must “love me for me.” Despite what they’ve read in the headlines,” she’s an actual human being with real feelings.

It’s a delicate balance, she relays — being herself and upholding preconceived ideas of who she is. But she walks that line like a tightrope acrobat. It also helps that ‘Delicate’ has one irresistible hook.

9. ‘Blank Space’

Taylor Swift has always been one to flip the media’s portrayal of her on its head. That’s clearly the case with ‘Blank Space,’ in which she admits to having a “long list of ex-lovers,” with a wink and a wry smile.

It’s self-critical but not overly so; it strikes a perfect balance between being honest with herself and making a joke out of the media. And it’s also wonderful that it contains one of her best pop hooks on 1989.

8. ‘Out of the Woods’

1989 saw Swift fully embracing pop. She had previously only tinkered in the space with 2012’s Red, but she found it was long overdue to leave country music behind and transform into the pop superstar she had always wanted.

‘Out of the Woods’ trembles with an almost earthy, rhythmic quality. Her voice pokes through the drip-drop of production to deliver a soaring vocal. From its sticky vocal distortion to the spacey percussion, the song is pure pop perfection.

7. ‘Anti-Hero’

“I’ll stare directly at the sun but never in the mirror,” Swift sings in one of her most self-deprecating lines. ‘Anti-Hero’ roots around in a critical headspace with the singer fully believing she’s the problem.

Dressed with heavy synth reverb and a bouncy backbeat, the smash single from Midnights is the sort of career-defining song that you can’t possibly ignore.

6. ‘Dear John’

From the album entirely written solo, ‘Dear John’ emerges as a near-seven minute epoch. Reportedly about her dating John Mayer, the fragile ballad allows Swift’s voice to puncture the air from the room.

It’s clear and crisp, brimming with a flood of emotion. “I’m shining like fireworks over your sad, empty town,” she wails. In the heartbreak, she learns the truth: her self-worth is far more important.

5. ‘Back to December’

In ‘Back to December,’ Taylor Swift confesses her sins in a relationship’s end. She longs to go back to the days when their love was hot and the night air was cool. “These days I haven’t been sleeping / Staying up playing back myself leaving,” she sings. Her admission of guilt eats her alive, leaving Swift to deliver an emotionally gagged performance.

4. ‘invisible string’

There’s a belief that fate operates like a piece of string, knotting two lovers to one another. That’s the emotional core of ‘invisible string,’ in which Taylor Swift muses on past romantic failures, the healing process, and her then-relationship with Joe Alwyn.

“Chains around my demons,” she sings. In one moment, a single thread tied and bound her to a new lover. It was out of her control, you could say. Flaky guitar strings characterize the song, one of folklore’s richest and folksiest moments.

3. ‘Clean’

Taylor Swift’s ‘Clean’ doesn’t get enough credit for perfectly capturing the fall from grace and a relationship’s dying out. “You’re still all over me like a wine-stained dress I can’t wear anymore,” she coos. In time, a torrential downpour leads to her freedom.

She drowned only to be clean again. Especially with Taylor’s Version of the song, ‘Clean’ is a perfect lyric wrapped in a perfect performance. “I think I’m finally clean,” she concludes.

2. ‘Enchanted’

‘Enchanted’ is Swift’s most, well, enchanting entry in her catalog. There’s just something magical about it, from the doting lyrics to the windswept production.

“This night is sparkling / Don’t you let it go,” she sings. She blushes; it’s a love-at-first-sight encounter. She later becomes restless and unable to sleep. The chance meeting can’t be shaken from her mind.

1. ‘All Too Well’ (10-minute version)

There’s no mistaking it: “All Too Well” is Swift’s crown jewel. Even though the original tune was 11 years old, the release of a 10-minute version was worth it. Swift configures the story with some of the richest detail in a pop song ever, and it never feels overwrought or lengthy.

Palpitating drums accentuate the emotional urgency, brushed with tender guitar and a haunting backing vocal. Decades from now, ‘All Too Well’ will be studied for its potent storytelling.