Taylor Swift’s best songs ranked: from Cruel Summer to All Too Well

Taylor Swift’s best songs ranked: from Cruel Summer to All Too Well

Taylor Swift has been at the top of her game for a long time: first, at 16, she arrived as a ready-made country star with records glistening like chrome bumpers on Ford pickup trucks, full of Nashville accents and wailing Telecasters.

Slowly, over the 18 years that have followed, the banjos have been packed away, and she has transformed into one of the world's biggest pop acts.

In an era of megastars – Adele, Beyoncé and Ed Sheeran – she has still somehow managed to break sales records and dominate the news cycle. She has built her empire the old fashioned way, on songs and shows, demonstrated her business knack through canny endorsements and has ended up as one of the most successful artists of all time (The Eras Tour is the highest grossing tour in history).

Even better, Swift is due to kick off her Eras tour in the UK tonight, playing in Edinburgh. She’ll be stopping off in Liverpool, then Cardiff, before finally taking the stage in London on June 21.

With her UK shows just days away, here’s our pick of her best songs, ranked.

15. I Knew You Were Trouble (2012)

2012 album Red took Swift's popularity to new levels and the universal appeal of I Knew You Were Trouble was a key part of that success. The song became one of the most parodied tracks of the year but even adding screaming goats into various joke remixes couldn’t hamper its impact. It’s perhaps surprising that despite the song’s success, the chorus marked one of the singer’s most experimental moments to date, flirting with dubstep, pop and dance influences. It’s the perfect example of Swift’s early musical experimentations – as was the U2-esque album opener State of Grace – which would eventually pave the way for a reinvention on 1989 two years later.

14. Shake It Off (2014)

Shake It Off is perhaps the perfect song to explain Taylor Swift and seems to encapsulate the contradictions which have made her a star. For everything that’s toe-curling and cringeworthy (see: “this sick beat”, the whole “my ex-man” riff), it’s also infectious, irresistible and triumphantly confident; Swift knows it’s geeky and doesn’t care. It’s a song to shimmy to – and then to kiss your crush to, when she asks the fella with the hella good hair to shake, shake, shake. Grab the white wine and go be basic – sometimes it’s fun.

13. 22 (2012)

While Swift can occasionally lean in on her wry way of seeing the world, she’s also gloriously unafraid of big, bold pop. 22 is almost comically simplistic: the opening guitar riff is just a watered-down Wild Thing, the drum beat is mindlessly insistent – a bass kick on every single beat – and the main hook (“I don't know about you, but I'm feeling 22”) isn’t exactly going to worry any hopeful Poet Laureates.

None of it matters; the song is a joyous riot, set in a world where there are no pressures, no bills and the sun only goes down so everyone can go to bed together. It is fun, silly, and infectiously single-minded. The best lines come right at the end: “You look like bad news, I gotta have you”. There’s even Nile Rodgers-style guitar thrown in on the chorus. Splendid stuff. No wonder it’s said to be Harry Styles’ favourite Swift song.

12. Fifteen (2008)

Much has been made of Swift’s big transformation from country singer to pop behemoth but even before she was out of her teens she was flirting with stadium-friendly rock. Still, Fifteen had plenty of banjo all over it, while her voice charmingly twangs as she talks boys and cars and heartbreak. Of which, it’s the lyrics that make this one: the song itself is so polished and clean it could have been assembled on a Tennessee production line, but Swift manages to infuse it with a sense of failed teenage romance that feels real – unsurprising, perhaps, given it’s based on her and her best friend Abigail Anderson’s years at Hendersonville High School.

“In your life you'll do things greater than/Dating the boy on the football team/But I didn't know it at fifteen” she sings, “Wish you could go back and tell yourself what you know now”. Ain’t that the truth.

11. Love Story (2008)

Fifteen years ago, pre-Kanye-at-the-VMAs, Swift was, in Britain at least, still that country girl with that one catchy song. This was that song; a hopelessly romantic tale of teenage love, Shakespeare’s Romeo & Juliet over pop-punk guitars and key changes and, of course, a happy ending replacing the tragedy. Eight million copies sold, making it the best-selling country single of all time and paving the way for the decade of massive success that followed.

10. Blank Space (2014)

Blank Space is a minimalist masterpiece that paradoxically is crammed with hooks (something she manages again, like a magic trick, on Clean). The song in itself is actually surprisingly slow-moving; chords are long, drawn-out and the drums snap but are unhurried. The genius here is in Swift’s vocals, which are catchy enough that the whole thing seems to be one long chorus. Blank Space also marks the beginning of Swift sending herself up; in it, she satirises her media image as a man-obsessed, relationship-addicted nightmare who serially dates for songwriting material.

Hilariously, the key line (“Got a long list of ex-lovers/They'll tell you I'm insane”) has often been misheard – including by her own mother – as “all the lonely Starbucks lovers”, which rather changes the point somewhat. The video is a work of art too, introducing the world to the ‘new Taylor’ – before the new Taylor became the old, dead Taylor.

9. New Year’s Day (2017)

The beautiful, reverb-soaked piano that flutters through New Year’s Day is a sign of what could be to come for Swift – not now, perhaps, but maybe in 20 years. It could be played then and will be just as good. If All Too Well is her great grown-up heartbreak track, this is her great grown-up love song. Whereas 1989’s You Are In Love used a similar sound for a rip of Bruce Springsteen’s Street’s of Philadelphia, here it’s more of a James Blake vibe.

The beauty is in the simplicity; this is a love song as rational as it is passionate. The metaphor is about being there for the good times (the party at midnight) and the bad (cleaning up bottles on New Year’s Day). There is a stroke of brilliance, too: “Please don't ever become a stranger whose laugh I could recognise anywhere” she sings as a reprise, realising what too few of us do until it’s too late: love is as fragile as it is precious.

8. August (2020)

This wistful hit from 2020’s folklore is Swift’s fifth most played song on Spotify, proving that the album’s genre shift paid off. It’s the third track in a trilogy that details a love triangle between August, Betty, and James, told from the point of view of the other woman, who each believed James was hers alone.

Like other Taylor hits, this one wasn’t released as a single, but became popular regardless. Written during lockdown and released in July 2020, August was the perfect melancholic song for a summer of isolation. It’s held up beyond lockdown, and has inspired (and will continue to inspire) captions for August Instagram round-ups for years to come.

7. You Belong With Me (2009)

Taylor has a long-standing love affair with power chords and pop-punk goodness. On Red, there’s Holy Ground, before that was Speak Now’s girl-breaking-free-to-rule-the-world Long Live and then there was You Belong With Me on Fearless. It’s sometimes criticised for being too similar to her other early hits but in truth, it’s just the best of the bunch. It’s also wonderfully full-on Taylor: she plays the self-deprecating dork in love with her best friend, and the video is completely, brilliantly hysterical. There are all the elements needed: crashing guitars, unrequited love, a little teenage angst.

It’s far from perfect: the lyrics are her corniest, the premise is cliched and the country embellishments have been tactlessly tacked on as if purely to placate the country audience. But, in the end, it’s catchy, sweetly endearing and you’ll be singing along merrily. If you want another fill of the good stuff, put on Fearless, which is just a little less catchy but with a better guitar solo.

6. Karma (2022)

Karma, from the 2022 Midnights’ album serves as a stark reminder to those who cross her (looking at you, Kanye) that Swift will always come out on top. But this time she’s swapped the spiky attitude from Reputation for a more joyful take on the matter.

Swift sings about the good things that have come to her, such as “the guy on the screen” (now “on the Chiefs”, as she sang in a viral moment on tour, giving a nod to her new beau Travis Kelce), and, in classic Taylor fashion, a cat “purring in [her] lap.” The fun, upbeat Midnights single has become a fan favourite on the Eras Tour, and at the time of writing, is Swift’s eighth most played song on Spotify.

5. Ronan (2012)

Little known, not on any albums and barely performed live – to date it’s only been aired twice, with the first version live on a Stand Up to Cancer telethon the one to listen to – Ronan perhaps seems an unlikely entry on the list, but it remains the Swift song that aches the most, and is unlike anything else she’s written.

Over the chime of trembling guitar chords, she sings as the voice of Maya Thompson, a mother who lost her four-year-old son Ronan to cancer. Written after reading Thompson’s blog, Swift articulates the unsteady, insistent rhythm of grief with painful clarity. In the end, like in life, the loss stings the sharpest in the little things. “And it's about to be Halloween, you could be anything you wanted,” she sings, her voice shaking and her eyes glassy with tears, “If you were still here.”

4. Out Of The Woods (2014)

Just like the heartbroken logic that fuels All You Had To Do Was Stay, it’s the naivety in this one that makes it so damned sad. Jack Antonoff produced a piece of driving rock dressed up as radio-pop, the stuttering drums and Blade Runner synths casting shadows over everything, the choir on the chorus giving it enough size to fill stadiums. It’s one for anyone who’s been wrapped up in a love that’s left them shaky with the uncertainty of it all.

3. Style (2015)

Like a designer parading a new collection down the runway, Swift showcased her new direction perfectly on this aptly titled track. Pulsating synths drive the verses along before a huge sing-along chorus kicks in, marking a dramatic change from her guitar-led earlier compositions. It’s a formula that Swift would return to time and time again in her later work, not least on the similar Getaway Car from 2017 album reputation. The song remains a highlight at Swift’s live shows — after all, pop hooks as good as this will never go out of style.

2.Cruel Summer (2019)

Cruel Summer didn’t receive the attention it deserved when it was first released on Swift’s 2019 album, Lover, with ME! inexplicably being chosen as the lead single instead. But the song finally hit the mainstream when Swift included it in her Eras Tour setlist in March 2023. It’s currently her most played song on Spotify, beating out Lover and Anti-Hero, and for good reason, too.

Cruel Summer features one of Swift’s best bridges – and she’s known for writing some excellent ones – that has had fans screaming “I love you, ain’t that the worst thing you ever heard?” in arenas around the world. When this plays on the radio, you can’t help but sing along at the top of your lungs.

1. All Too Well (both versions)

Both versions of All Too Well pack a punch. The original, which was released in 2012 when Swift was in her early twenties, was Swift’s most sincere tale of heartbreak to date. Though it took a handful of listens to ‘get’ the track, it’s worn out and weary pace perfectly captured Swift’s low mood. Swift says it was one of the hardest to write, and it’s one of the hardest to listen to; she sounds like she’s singing right from her bones and it’s searingly, uncomfortably intimate.

Having it on doesn’t feel so much like listening as eavesdropping: other ruminations in her back catalogue are broader and more relatable – here we’re hearing her specific turmoil. Nowhere else on record does she sound as cut up the way she does halfway through this one – Jake Gyllenhaal, you realise, really broke her heart.

Then in 2021, now with nearly a decade of extra life experience behind her, Swift released Red (Taylor’s Version) a re-recording of her 2012 album, Red. It included two new versions of All Too Well: a re-recording of the original version, and a 10-minute version which was said to be “from the vault” – it included parts of the 2012 song that had been left on the cutting room floor. The 10-minute version soared to the top of the charts, becoming the longest song to ever reach number one in the US single charts.

But for fans, the success of the re-release was less about the stats, and more to do with the lasting power of the song. Its reimagining a decade later (and the short film that Swift directed which accompanied the release) confirmed what fans already knew: All Too Well was, and is, an utter banger.

Taylor Swift’s The Eras Tour arrives in London on June 21