Most artists would be content with a handful of chart-topping albums, but not Taylor Swift. Her famously relentless work ethic has resulted in 15 albums (counting rerecordings) in 22 years, being crowned the first artist to win four Grammy awards for Album of the Year, and a staggering 114 million albums sold worldwide. So which is her best?
15. Midnights (2022)
Flanked on stage by her super-producer Jack Antonoff and close friend Lana Del Rey, Swift accepted her fourth Grammy award for Album of the Year – becoming the first artist to do so – back in February by thanking her fans, saying: “All I want to do is keep being able to do this”. It’s just a shame her crowning achievement was for an album as middling as Midnights, a repetitive collection of 13 songs themed around her restless late nights. Lead single Anti-Hero, Del Rey collaboration Snow on the Beach and the beautifully raw You’re On Your Own, Kid (the fact the latter isn’t a permanent feature on the Eras tour is criminal) are up there with Swift’s best, but the rest of the album simply isn’t as heartfelt or interesting as her other work.
Best song: You’re On Your Own, Kid
14. Taylor Swift (2006)
When Swift released her debut album in 2006, aged just 16, she seemed like the saving grace country music had been waiting for: the all-American good girl, with her tight blonde curls and tender songs about teenage heartbreak, who could move the genre on from dominant older performs like Reba McEntire, Faith Hill or Shania Twain (and controversial ones like the Chicks). After watching a documentary about Hill, Swift – who had long since dreamed of a career in music – persuaded her parents to up sticks from Pennsylvania to Nashville, Tennessee so she could make the big time. It’s a simple album, both sonically and lyrically – she sings of smalltowns and out-of-reach relationships, backed by her acoustic guitar – which explains its low ranking. But it’s heartfelt and pure, too, and signalled from the get go that Swift was a songwriting talent to reckon with: Teardrops On My Guitar is one of her finest love songs.
Best song: Our Song
13. Speak Now (Taylor’s Version) (2023)
My personal favourite Swift album, 2010’s Speak Now was quintessential country-pop filled with juvenile metaphors (there’s castles and dragons and knights in shining armour). Her first entirely self-written album, it gave us reflective ballad Long Live, the ultimate fan favourite, and the pop-punk twinged The Story of Us, Better Than Revenge and Haunted. How disappointing it was to find, then, when Swift released ‘Taylor’s Version’ of the album last year, that she’d changed the lyrics on Revenge (“She’s better known for the things that she does on the mattress” was considered sexist and dropped, even though she was between 18 and 20 when she wrote it – teenage girls get angry at other girls!), slowed down the tempo and muted the guitars on virtually every song, and brought close friend Hayley Williams (of rock band Paramore) on to feature on Castles Crumbling, which turned out to be less of an angsty anthem, more half-hearted afterthought.
Best song: Enchanted
12. Fearless (Taylor’s Version) (2021)
‘Taylor’s Version’ of the country-pop album that made her a star suffers from the same curse as 1989: the original was so flawless that any changes – however miniscule – seem wrong. Hits such as Love Story and You Belong With Me are slowed down ever so slightly, reducing their impact, although Swift’s vocals on the more demanding ballads – Fearless and The Way I Loved You – sound richer. The Other Side of the Door, a vastly underrated track that features one of Swift’s strongest bridges (“And I broke down cryin’, was she worth this mess?”) is the song that comes alive most.
Best song: The Other Side of the Door
11. Evermore (2020)
The second of Swift’s pandemic sister albums lacked Folklore’s clarity, but as a collection of songs taken to represent that shattering, uncertain time in human history – when people were locked down, families ripped apart and left to grieve alone – it still demonstrates her versatility. Co-produced by The National’s Aaron Dessner and her usual collaborator Jack Antonoff, soft, floating strings and weightless pianos support songs about forbidden love (Ivy), romantic neglect (Gold Rush), and even homicide (No Body, No Crime, featuring indie band HAIM). Many blend into one hom*ogenous blob of sadness, though Champagne Problems – a furiously emotional pushback to the critics who called her crazy and said she’d never find love (“She would’ve made such a lovely bride / What a shame she’s f—ed in the head”) – earns its place in the Swift hall of fame.
Best song: Champagne Problems
10. Lover (2019)
It opens the Eras tour and spawned Swift’s now-biggest hit, Cruel Summer, but Lover has always paled in comparison to her more personal, raw and emotional albums. Swift’s seventh studio album was the first she fully, legally owned herself, and it’s a glittering pink-force of a pop album, mostly centred on how much she loves Joe Alwyn, loathes sexist double standards (especially Leonardo di Caprio, on The Man) and doesn’t understand hom*ophobes (You Need to Calm Down). The bubblegum-sweet sheen is removed, fleetingly, for gorgeous ballad Daylight, in which Swift throws herself, hook, line and sinker, into romance.
Best song: Cruel Summer
9. 1989 (Taylor’s Version) (2023)
1989 is a perfect pop album, mixed by one of the industry’s most innovative producers (Max Martin), with heaps of vivacious energy. That’s what made Antonoff’s slowed-down spin on so many songs on ‘Taylor’s Version’ most disappointing – they didn’t need tampering with! Style, in particular, sounds vastly inferior to the original. Thankfully, the unreleased Vault tracks that arrived with the album were the finest thus far, as Swift sings of young yearning (Say Don’t Go, Suburban Legends), gendered shaming (on slu*t!) and accepting that a relationship has reached its end-point on the simultaneously entertaining and moving Is It Over Now?
Best song: Is It Over Now?
8. The Tortured Poets Department (2024)
With 31 songs on the full tracklist (Swift is now so famous she apparently doesn’t have an editor), Tortured Poets Department is the sort of album that rewards repeated listening. There are plenty of inferior songs that should have been cut, but a few stand out: The Smallest Man Who Ever Lived, a cascading f–k you to former lover Matty Healy who double-crossed her and “deserves prison / But you won’t get time”; So High School, that leans heavily on the pop-punk angst of Paramore and Swift’s Speak Now singles to declare her love for NFL star Travis Kelce; and So Long, London, a melancholy goodbye to the city she called her second home for six years while dating Alwyn. What let TTPD down was its production – after almost a decade of working with Antonoff, who favours minimalism and retro-synths over thrashing instruments or electronics, it seemed predictable and staid.
Best song: The Smallest Man Who Ever Lived
7. Red (2012)
Pop anthems like We Are Never Ever Getting Back Together, 22 and I Knew You Were Trouble opened Swift’s music up to a whole new audience, while her personal life – especially relationships with famous men, including Jake Gyllenhaal, and photo-ready celebrity “girl gang” – made her regular tabloid-fodder. Red is still Swift’s quintessential album, containing all the elements of the different genres – country, pop, indie – that have made her a star. And in All Too Well, somehow made even better in 2021, she made her masterpiece.
Best song: All Too Well
6. Speak Now (2010)
Filled with fairytale princesses whiling away their days in far-flung castles, guarded by dragons and waiting on white knights, Speak Now is undoubtedly Swift’s most teenage album. That’s part of its charm, however, from the soaring balladry of Enchanted and Back to December to tearing apart teenage bullies who doubted her talent on Mean. Long Live, a powerful ode to her live band and loyal fans, remains the most shattering song in her arsenal.
Best song: Long Live
5. Fearless (2008)
It was Fearless that transformed Swift from teenage Nashville favourite to global megastar – and it also spawned her much-publicised row with West, after he interrupted her acceptance speech at the VMAs in 2009 to inform the audience that Beyonce should have won instead. Filled with good-will, heart and genuine insight to what it means – and feels like – to be a teenage girl, songs like the Romeo and Juliet-inspired Love Story, angsty You Belong With Me (and its aforementioned award-winning video) and Fifteen, a tender warning to not settle for second best (even if he is “the boy on the football team”) set her up as the voice of a generation.
Best song: You Belong With Me
4. Folklore (2020)
Co-written and produced with The National’s Aaron Dessner, Folklore marked the first of Swift’s pair of lockdown-era albums (with Evermore). Its stunning display of indie-folk, coupled with Swift’s decision to swap biographical lyrics for fictional characters (on the likes of Betty and The Last Great American Dynasty), earned her another Grammy for Album of the Year, and secured her position as one of our finest songwriters. For those unsure about Swift, it’s the perfect place to start.
Best song: Exile (featuring Bon Iver)
3. Reputation (2017)
Upon release, Reputation’s fiery singles (Look What You Made Me Do, …Ready For It?, I Did Something Bad) were the ones that populated the headlines. Little surprise, considering they were widely seen as Swift’s way of addressing her bitter feud with Kanye West and Kim Kardashian. But peer beneath the R&B-influenced, brashly gutsy pop veneer and you’ll find Swift’s greatest love letters, penned to her then-boyfriend Joe Alwyn. King of My Heart, Call It What You Want and Delicate celebrate how he fell in love with her despite the naysayers, who warned she would only rip him apart in her songs; Dress ramps up the sex-factor to thrilling effect. The final song, New Year’s Day, dials down the electro-beats and fancy production for a piano and guitar-led ballad set the morning after a party, when Swift and her beau find themselves, closer than ever, reflecting on the night before – and the year to come.
Best song: New Year’s Day
2. 1989 (2014)
Made with Swedish super-producer Max Martin, 1989 catapulted Swift into the stratosphere. And it’s easy to see why – it’s a perfect pop album, jam packed of nostalgia Eighties-esque synths and snares, addictive, catchy earworm hooks and knife-sharp lyrics (Blank Space’s “Cause darling I’m a nightmare dressed like a daydream,” anyone?) Bar the skippable Bad Blood, every song on 1989 is a masterpiece in how to craft memorable but accessible pop music – from the fairytale dreaming of Wonderland to glorious optimism on New Romantics and atmospheric catharsis on Clean. Style, though, a thinly veiled ode to Harry Styles (who she briefly dated) towers above the rest as the finest pop song she’s ever made – and arguably the finest pop song of the past two decades.
Best song: Style
Red (Taylor’s Version) (2021)
Back in 2012, Swift decided to reinvent herself, abandoning her country roots in favour of pure radio-friendly pop. Red is the perfect introduction to her music, though, because although it marks a shift, it retains the emotional vulnerability, innocence and wit that characterised her early albums; she wasn’t, yet, too famous to seem out of reach. Unlike her other rerecordings, Red (Taylor’s Version) was a dramatic upgrade: the instruments are finer tuned, hinging on shuddering electric guitars and danceable beats, while her voice – not, naturally, her strongest attribute – sounds deeper and more mature.
But it’s the arrival of her opus, the 10 minute update of All Too Well, that makes this version of Red a towering presence in her back catalogue. Released alongside a short-film starring Stranger Things’ Sadie Sink, it’s a devastating rumination (widely believed to be about Gyllenhaal) on how lost love and disappointment can shape you. “And you call me up again just to break me like a promise / So casually cruel in the name of being honest” she sings, and your heart breaks with her. Performed in full at the Eras tour, it’s possible that this is Swift’s imperial offering, her Born to Run or Let It Be.
Best song: All Too Well (10 minute version)
