‘Phenomenon” is, by now, insufficient to describe Taylor Swift. She is simply a ubiquitous part of our culture, as much as pop music itself. But is she really that good? And is it too late for you to try to get into her music with her UK tour underway? The respective answers to those questions are a firm yes and no.
As deft a lyricist as Joni Mitchell, as varied as — actually, no modern singer has worked in as many genres as Swift, who hops easily between country music, bubblegum pop, harder-edged rock, electronic, folk and on and on, and owns them all. But with such a catalogue — 11 studio albums and counting — it can be difficult to know where to start. So, assisted by my favourite fellow Swiftologist, my 11-year-old goddaughter Léa, I have compiled our favourites. How did we limit ourselves to only 20 of her magnificent songs? With huge difficulty, is the answer.
20. Our Song (Taylor Swift, 2006)
When I was 17 my only ambition was learning how to put on eyeliner. Swift aimed higher and released her first album. She wrote this one for her Year 9 talent show — yes, really — and while it’s undeniably country, even the most banjophobic can’t resist the sweet lyrics and tune. “Our song is the way you laugh/ The first date, ‘Man, I didn’t kiss her and I should have.’ ”
19. Cornelia Street (Lover, 2019)
Oh man, I love the whole of this lush, romance-soaked album, written in the first flush of Swift’s love for her boyfriend at the time, Joe Alwyn. So many tracks deserve inclusion here: The Archer, Lover, Death by a Thousand Cuts. Cornelia Street is one of her sweetest songs, as she imagines how painful it will be to remember the apartment she and Alwyn shared should they ever break up, which, alas, they later did. Oh, Taylor —you’ll never walk Cornelia Street again.
18. I Can Do It with a Broken Heart (The Tortured Poets Department, 2024)
I have no time for the naysayers when it comes to the most recent album. Who’s Afraid of Little Old Me?, Loml and My Boy Only Breaks His Favourite Toys are fantastic songs, but this one is the real crowdpleaser, joyfully describing how heartbroken she’s been on the Eras tour. That her tears were for the 1975’s Matty Healy is inexplicable. But this song’s status as a proper banger? Undeniable.
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17. Champagne Problems (Evermore, 2020)
Co-written with her now ex-boyfriend Alwyn (under the pseudonym “William Bowery”), this is Swift at her most slyly vicious. She imagines a former lover’s self-indulgent sadness after she rejected his misguided marriage proposal at a Christmas party. “Champagne problems” becomes a signifier for the doomed party, his self-pity and, ultimately, her self-destructiveness. She wields the knife with the deftest of touches.
16. The Last Great American Dynasty (Folklore, 2020)
When Swift released her two surprise folk albums in 2020 — Folklore and Evermore — not even the most stubborn of cynics could deny her greatness. She has always been terrific at narrative songs (see: The Lucky One on Red), but this one — co-written with the National’s Aaron Dessner — is especially fine, imagining the life of the socialite who lived in her house before she did. Just phenomenally good lyrical writing accompanied by elegantly catchy folktronica.
15. Getaway Car (Reputation, 2017)
It’s not essential to know that this song — which imagines a couple being pursued in a car by an angry former lover — is allegedly about Swift’s break-up from Calvin Harris and her rebound relationship with Tom Hiddleston. But it doesn’t hurt. From Swift’s controversial (at the time) harder-edged album Reputation, this is one of her great switcheroo songs (new official term), where the storyline shifts unexpectedly at the end. Intricate, clever and with a great synth melody.
14. Mastermind (Midnights, 2022)
Swift was inspired to write this after watching Paul Thomas Anderson’s film Phantom Thread, about a conniving seamstress. Which means, yup, another switcheroo song (see above). She describes plotting to get a guy, then reveals why she has to be Machiavellian about these things (“No one wanted to play with me as a little kid/ So I’ve been scheming like a criminal ever since”), then realises the guy knew all along. Tchuh, men!
13. Holy Ground (Red, 2012)
I just love this foot-stompin’, rootin’-tootin’ look back at a once happy relationship. It was on Red that Swift made the conclusive pivot away from country and towards pop, and it’s striking that some of the strongest songs on the album include both. Holy Ground is like Britney Spears mixed with Dolly Parton, and the result is as anthemic as Billy Idol.
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12. The Tortured Poets Department (The Tortured Poets Department)
Many a woman has dated a tortured poet. None has described it as beautifully as this: “You’re in self-sabotage mode/ Throwing spikes down the road/ But I’ve seen this episode and still loved the show/ Who else decodes you?” No wonder that poet is tortured when his (ex)girlfriend writes so much better than him. Patti Smith thanked Swift for including her in it, and if Dylan Thomas were alive, he would have too.
11. We Are Never Ever Getting Back Together (Red)
A perfect example of how Swift brought her country music beginnings and transmuted them into pop perfection. But as ever, it’s the lyrics that knock you out: “I’m really gonna miss you picking fights/ And me falling for it, screaming that I’m right/ And you would hide away and find your peace of mind/ With some indie record that’s much cooler than mine.” The funniest break-up song since You’re So Vain.
10. Out of the Woods (1989, 2014)
The great Taylor Swift-Jack Antonoff co-writing partnership ostensibly began with this, a recollection (allegedly) of Swift’s relationship with Harry Styles that evokes all the hope and insecurities of a couple’s early days. An absolutely mega pop song that contains Swift’s trademark poetic stylings, and a chorus that defines the description “hooky”.
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9. Love Story (Fearless, 2008)
Travis Kelce is doomed for ever to have people playing this song every time he walks in a room, thanks to all those TikToks showing him and Swift dancing to it after his team won the Super Bowl this year. Well, there are worse fates (just ask Jake Gyllenhaal — see song No 1). As starry-eyed as you’d expect of a love song written by a girl barely out of her mid-teens (yes, really), but with an infectious melody that songwriters three times her age would kill to write.
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8. Exile featuring Bon Iver (Folklore)
Honestly, so many songs from Folklore and Evermore deserve to be in this list: The 1, Cardigan, August, Betty, ’Tis the Damn Season, Marjorie … But such are the riches of Swift. This dissection of the end of a relationship from both sides is one of the most poignant things she has written, and it skilfully uses one of her favourite tropes: seeing an affair through the prism of a film.
7. Cruel Summer (Lover)
Pure anthemic pop that begs to be sung at top volume in a stadium. Cruel summer may well be the precursor to sad autumn, according to Swift’s theory of seasons, but with Jack Antonoff and St Vincent on co-writing duties, it also makes the shy early days of love sound about as tentative as a hurricane. Irresistible, so don’t even try.
6. Anti-Hero (Midnights)
Only the dumbest of Swift snarkers still dismiss her as a purveyor of sappy love songs. She’s long been unpeeling a far more interesting persona, never more so than in this, one of her cleverest songs. The music is woozily electronic, but the lyrics are pin-sharp as she sums up all her evil ways: “Did you hear my covert narcissism I disguise as altruism/ Like some kind of congressman?”
5. Begin Again (Red)
In four minutes, Swift describes the end of one relationship and the beginning of another. Every couplet is so packed with detail, you feel like you know everyone involved. Just look at the chorus: “You throw your head back laughing like a little kid/ I think it’s strange that you think I’m funny ’cause he never did.” With its melodic guitar strumming it could be a James Taylor song, and that’s no accident. After all, as she tells us: “You said you never met one girl who/ Has as many James Taylor records as you/ But I do.”
4. Style (1989)
With its instantly distinctive intro and bright, glossy instrumentals, this feels like it was written to soundtrack a romantic montage in a 1980s movie. Along with the pop supremo producer Max Martin, Swift plays with her signature self-consciously traditional tropes — she’s a good girl with red lips; he’s a dreamy-eyed bad boy — to create a deliciously knowing pop song, one that flirts with the darkness of Rebel Without a Cause but is as delightful as Pretty in Pink.
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3. You Belong with Me (Fearless)
Fun fact: it was when Swift won the 2009 MTV best female video award for this over Beyoncé’s Single Ladies (Put a Ring on It) that Kanye West stormed the stage in outrage. Hey, whatever happened to him? This was written when Swift was, unbelievably, 17 years old and her easy combining of genres (country and pop) and fantastically concise storytelling were all in early evidence here. Too young to drink in the US, but old enough to write this indelible ode to teenage love. And did Swift predict her relationship with Travis Kelce 16 years before it happened? The video suggests so.
2. Blank Space (1989)
As soon as the drum pads and synths kick in, it is clear that Swift is entering her imperial phase. It starts off as a song about meeting someone new, then switches to satirising Swift’s image as a man-eating harpy. It is both epic and subtle, funny and powerful, the song on which she proved she could bring her lyrical brilliance to 1980s synth big beats. And the fact we all initially misheard the lyric “Got a long list of ex-lovers” as “All the lonely Starbucks lovers” somehow made it even more addictive.
1. All Too Well (ten-minute version) (Red, Taylor’s Version, 2021)
Is a ten-minute opus about a six-week relationship this century’s The Rape of the Lock? Yes. Is it also one of the most majestic break-up songs yet written? Again, yes. Her short fling with Jake Gyllenhaal left Swift with a broken heart, but it also inspired her greatest song. Musically indebted to Bob Dylan’s Visions of Johanna, Swift makes it all her own. Anyone who claims there’s a better break-up couplet than “You call me up again just to break me like a promise/ So casually cruel in the name of being honest” is lying. A gorgeous, cathartic, sing-along masterpiece.
What’s your favourite Taylor Swift song? Let us know in the comments below
