Taylor Swift’s eras ranked from worst to best

The cultural phenomenon we’ve been waiting for is here: Taylor Swift’s Eras tour, her 3½-hour live journey through her 10-album discography, is upon us, a biblical moment without historic precedent. Too hyperbolic? Please, just let us have our fun.

At 34, Taylor’s already been dominating pop music for almost two decades. But which era is her best? And which one’s due a cultural reevaluation? Ahead of her Australian gigs, we’re diving into the key phases of our generation’s defining pop star and we’re picking sides (we’re ranking them, ’cause we all love rankings). Let the arguments begin.

10: Taylor Swift (2006)

Taylor Swift in her teenage cowgirl meets Disney mermaid era.Credit: Getty Images

The music: In the beginning, there was Country Taylor. Swift’s self-titled debut – recorded in her first year of high school, and released when she was 16 – quickly turned her into a country star in the US; she won the Country Music Association’s award for new artist of the year in 2007.

If it’s her weakest album, it’s only because of its genre limitations (all those banjos and broke-down Chevys). But listen and you’re instantly struck by the bizarrely mature songwriting and the seeds of future Taylors present – from the outsider perspective, yearning romance and poetic specificity of Tim McGraw and Teardrops On My Guitar, to the bitter kiss-offs Cold As You and Picture to Burn, a stone-cold classic. She’s largely eschewed these songs on her Eras tour (with the occasional exception of Tim McGraw or Our Song), but it’s to be expected: that’s like if Picasso stuck with blue into middle-age.

The aesthetic: Look, it’s a lot, but what were you wearing when you were 16 years old? This is teenage cowgirl-meets-Disney mermaid Taylor, down to the rodeo boots and sparkly slip dresses. Onstage, she’d often sing these songs under artificial rain.

The relationships: It was an innocent time, before Taylor’s dating history drove a global news industry. These were classmates, random crushes with names like Drew who went on to join the military. She wrote Our Song for her high school talent show, for chrissakes. But how quickly things change: by mid-2008, Swift was dating Joe “Purity Ring” Jonas.

The moment: Taylor’s barnstorming performance of Should’ve Said No at the 2008 CMAs is everything – wonderful, dramatic, cringe, over-the-top, showstopping – from its ridiculous costume reveal to wet theatrics. If you witnessed this live in 2008, I don’t see how you wouldn’t have been convinced that Taylor Swift would be a generation’s defining pop icon. RM

9: Evermore (2020)

Taylor Swift in her poetic Evermore era.Credit: Getty Images

The music: I think of Evermore as the older, wiser sister of Taylor’s other pandemic pivot Folklore, which was released just five months earlier. If Folklore is the dying days of the summer, then Evermore is the autumn falling into winter.

There are more chamber pop elements on this album, such as the finger-picked guitar that introduces Willow and flute, glockenspiel and keys throughout. Bon Iver returns for another duet on the moody Evermore, and The National singer Matt Berninger lends his signature baritone to Coney Island.

Swift’s knack for storytelling is even greater on this album – Ivy might be one of her most underrated songs, telling the tale of a sapphic love that could never quite be. Marjorie, a touching ode to Swift’s grandmother, is composed of wisdom handed down generationally, as well as being a reflection on grief and loss.

On the other end of the spectrum there’s the delightfully deranged No Body No Crime featuring Haim – it follows the classic country murder ballad format and has some of the album’s strangest and most fun lyrics. It sowed the seeds for later songs such as Vigilante Shit.

The emotional maturity of Evermore is also evident on songs such as Closure and Happiness. There’s a much more poetic feeling to this album than any of its predecessors, and it’s a shame it’s often overlooked when talking about Swift’s discography and work.

The aesthetic: Think late autumn colours: oranges, browns, yellows, reds. Plaid shirts, woollen jackets and anything cosy.

The relationships: Evermore found Taylor very much in the midst of her Joe Alwyn era, who she dated for six years until they split in 2023.

The moment: On the Grammys stage in 2021, Swift performed a medley of songs from Folklore and Evermore – Cardigan, August and Willow – that gave a hint of what was to come with the Eras tour. Dark, theatrical and stunningly cohesive, it was a great introduction to her return to the world stage. GN

8: Lover (2019)

Taylor came into her own as a public figure in her Lover era.Credit: Getty Images

The music: Lover is the relative calm after the storm that was Reputation, and Swift’s first album released after she severed ties with Big Machine Records amid the label’s sale to Scooter Braun, who she accused of bullying. Her third album produced with Jack Antonoff, it’s a sparse, light affair – even if it does also boast her first explicitly activist songs in the pointed The Man and the pro-LGBT anthem You Need to Calm Down, a natural extension to Swift’s political coming out ahead of the US’s 2018 midterms.

If it feels thematically disjointed, it also boasts some great songs – Lover and I Think He Knows, with their slinky flirtations and idiosyncratic specifics, are gorgeous, and Cruel Summer (co-written with St Vincent) has become one of Swift’s biggest hits thanks to a TikTok rediscovery. Based on its ranking here, there’s a case that Lover might be Taylor’s most underrated era; I mean, there’s a reason she opens her Eras tour with it, right?

The aesthetic: Like the album’s cover, it’s pastel blues and pinks and oranges, all warm and cosy. Lover feels like the era where Taylor came into her own as a public figure, confident and comfortable with the ever-present circus. Without Lover, do we ever get to Taylor snuggling her tight-end boyfriend in the middle of a packed stadium while cameras hover? I don’t think so.

The relationships: As the title suggests, this was Taylor at her most coupled. By the time the album came out, she’d been with Joe Alwyn for three years and the songs are breezy and cheesy in the way long-term couples are. I mean, have you listened to London Boy?

The moment: Swift’s Lover-era transformation is made explicit in the Netflix doco Miss Americana when she posts her infamous Instagram note endorsing the Democratic candidate in the 2018 midterms, against the wishes of her team. “Something is different in my life, completely and unchangeably different since the sexual assault trial last year,” she says, citing the defamation trial she won in 2017 against a DJ who groped her. “No man in my organisation or in my family will ever understand what that was like.” RM

7: Midnights (2022)

Taylor Swift in her Midnights era of Eras.Credit: AP

The music: If not immediately impressive, Midnights feels like an amalgam of recent Taylor modes: its mid-tempo sonics, largely produced by Jack Antonoff, hark back to Lover; its intricate rhyme structures echo Folklore and Evermore; and its best moment, lead single Anti-Hero, is a sly Reputation-esque nod from Taylor towards her polarising public persona.

At this year’s Grammys, Midnights earned Swift her fourth album of the year win, a new record displacing imitators to the crown such as Stevie Wonder and Frank Sinatra. Deserved? Personally, I was tilting for SZA. But being a peerless zeitgeist juggernaut should always win you a big prize.

The aesthetic: Lavender haze, midnight blue, splashed burgundy. Smeared makeup at 3am and, of course, friendship bracelets.

The relationships: After Swift’s six-year relationship with Joe Alwyn ended in April 2023, she was understandably feeling herself. She dated Matty Healy for barely a month in May, until The 1975 singer’s mistimed edgelord era became a public liability. In June, NBA Twitter went wild with (false) rumours that Swift was dating Lakers star Austin Reaves. But then in September, reports that Swift was dating Kansas City Chiefs tight-end Travis Kelce were confirmed when Taylor was pictured alongside Kelce’s mum in the box at the Chiefs’ game against the Chicago Bears. And now Traylor’s going to the Super Bowl.

The moment: We’re in it. It’s Swift’s Eras tour, which has already become the highest-grossing concert tour in history with over a billion in earnings, and has catapulted Swift into an era of peak ubiquity (so much so that she’s suddenly become the subject of government psy-ops conspiracy theories). RM

6: Speak Now (2010)

Taylor Swift in her Speak Now era, one of finding and losing love.Credit: Getty

The music: Speak Now is the sound of a young woman coming into her own. On Swift’s third album, released in 2010, there’s a sense that she was keen to prove herself in the face of detractors – it is, to date, the only Swift album that is entirely self-written.

Much of Speak Now’s thematic content revolves around experiences of finding and losing love; it makes sense, seeing as Swift was then entering her twenties and teenage love can hit the hardest. Regarding the former, see opening number Mine (with the lyric “you made a rebel of a careless man’s careful daughter”, telling an entire story in a single line) or the starry-eyed Sparks Fly. The dreamy, wide-eyed Enchanted is rumoured to be written about a one-time encounter with Owl City’s Adam Young (he recorded a response track, which might be just about the cheesiest thing that’s happened within Swift’s career).

Not all of this album has aged well – Swift addressed that by changing the lyrics in Better Than Revenge to be less misogynistic – but Speak Now does a good job of, well, speaking to a certain time in Swift’s career, when she began to understand her own power and wield it on her own terms.

The aesthetic: Pinks and purples are the Speak Now era colours, not only because of the outfits Swift wears on the original and re-released covers, but also the gorgeous purple princess dress she wears during some performances in the Eras tour.

The relationships: The songs about heartbreak might be where the album shines brightest. Dear John, Swift’s kiss-off to ex-boyfriend John Mayer, is a brutal and brilliant condemnation of men who take advantage of younger women (its sequel of sorts, the quietly furious Would’ve, Could’ve, Should’ve, is a bonus track on the 3am edition of Midnights). Back to December, mourning Swift’s relationship with Taylor Lautner, might be the only ex-boyfriend song that’s complimentary towards the man in question.

The moment: Closing track Long Live is a highlight on this record. It’s Swift’s love letter to her fans, thick with fantastical imagery of castles, dragons and open skies, and it still sends shivers down my spine over a decade after I first heard it.

The performance of the track, from the Speak Now tour, captures the magic of being at a Taylor Swift concert, and also has some of Swift’s signature looks of the time, from the sparkly guitar to the hair curls. GN

5: Red (2012)

Taylor Swift in her Red era, when she shifted pointedly from country to pop.Credit: Getty

The music: Red is to Taylor Swift what Blue was to Joni Mitchell – the iconic singer-songwriter’s 1971 album is one of Swift’s all-time favourites, and the influence is clear on her own 2012 record. Both chart the all-encompassing experience of heartbreak, and for Swift this was when her songwriting took on a new depth. Some of the storytelling of Folklore and beyond was teased here – see Starlight, based on the love story of Ethel and Bobby Kennedy (Swift briefly dated their grandson, Connor, during this era).

Interestingly, Red was also the era where Swift shifted pointedly from country to pop. There were still hints of the former, but singles like We Are Never Getting Back Together, 22 and I Knew You Were Trouble – the latter wading into dubstep territory (and launching a thousand goat memes, if you know you know) – marked a concerted turn towards the pop sound that Swift would expand on for her next album, 1989.

The aesthetic: Visually, Red was all about striped tees, bowler hats and the now-infamous “not a lot going on at the moment” T-shirt that she donned in the 22 music video. At her Eras tour, she has been paying tribute to this by handing a lucky fan the hat during her performance of 22.

The relationships: Though the relationship was over by the time Red was released, the album is synonymous with one of her most famous exes, Jake Gyllenhaal, who’s the subject of the vivid breakup ballad All Too Well. The song took on even further resonance when Swift released its 10-minute extended version – and short film – in 2021. Swift’s eye for specific detail is what made this such a keeper: “Here we are again in the middle of the night/ we’re dancing round the kitchen in the refrigerator light” is such an evocative image that says so much about the giddy stages of new love, and what we remember when something is over.

The moment: Swift’s performance of All Too Well at the 2014 Grammys proved just how adept she is at singing live, as well as how emotionally wrenching the song is. As the performance goes on, she gets more into it, whipping her hair back and forth. Iconic. GN

4: Folklore (2020)

Taylor Swift in her Folklore (and pandemic) era.

The music: Where were you when Taylor Swift surprise-announced Folklore? The songwriter gave fans a heads-up that her eighth album would be released a mere 17 hours in advance; the fact that it was in the middle of lockdown, when literally nothing else was happening, made it even more exciting.

But what was most surprising was the new sonic direction Swift took with Folklore. It was the first of her now frequent collaborations with Aaron Dessner of The National, and saw a shift to a more folky, indie rock sound. Bon Iver’s Justin Vernon featured on the haunting duet Exile, his voice and Swift’s providing perfect foils to one another.

Folklore also marked the moment when Swift’s writing became less diaristic. These are the songs of a storyteller, inhabiting the inner lives of different characters and tracing the contours of their emotional truths. Take the triptych of Betty, Cardigan and August, documenting a teenage love triangle from the perspective of each of the three characters: boy cheats on girl and regrets it, woman looks back on her wild teenage drama, the other woman laments what never really was. Or Illicit Affairs, a compelling and harrowing portrait of infidelity from the perspective of the other woman. It’s masterful, meticulous stuff.

Swift also got a little more daring on this album, dropping the first F-bomb of her career in the quietly furious Mad Woman. That track is worth singling out because of its truth-telling approach to feminism, pointing out the gaslighting that surrounds any discussion of women’s anger and emotions. She hasn’t done anything quite like it before or since. The first album of Swift’s thirties marked a whole new era.

The aesthetic: True to the woodsy, cosy feel of the record, the look of this era was all about earthy colours – and a cardigan as an official piece of merch was a stroke of pure genius.

The relationships: By this point, Swift was in a long-term relationship with now-ex Joe Alwyn. The two worked together on Folklore, with Alwyn co-writing Exile and Betty, and later receiving co-production credits on a number of tracks (the Swiftie conspiracy theorists have a bit to say about the latter). The point is, though, that the boyfriend drama was well behind Swift by now – Alwyn had become a part of her work in a much more intimate way.

The moment: Folklore: The Long Pond Studio Sessions is worth a watch and a listen. Both a documentary and concert film, it was released at the tail end of 2020 and goes into some of the creative process behind Folklore. You might even call it her Bon Iver era – Long Pond Studio, owned by Aaron Dessner, is a small cabin in the isolated forests of the Hudson Valley in New York. GN

3: Fearless (2008)

Taylor Swift in her Fearless era, where the twang was less but country showmanship strong.Credit: Getty

The music: Released in Australia in March 2009, months after Taylor turned 19, Swift’s second album inched her away from country to pop-rock, and – more notably – to global stardom, thanks to the breakout success of the majestic Love Story, her first number one in Australia, and You Belong To Me, the ur-Taylor anthem.

Fearless is the ultimate example of Taylor as lovelorn romantic – these are grand songs, earnest and youthful and full of bighearted emotion, that could change your life if you possess the perennial soul of a sensitive teenage girl (it’s me, hi). Fifteen is heartbreaking in its intimacy; White Horse is brutal in its disenchantment; The Way I Loved You is coming-of-age confusion in a perfect fist-pumper. It’s not hard to see why Fearless won Taylor her first Grammy for album of the year in 2010.

The aesthetic: The twang might’ve left Taylor’s music, and her style started tilting towards her hero Stevie Nicks (leather and lace), but the country showmanship was just as big.

I saw Taylor perform this album at Sydney’s Factory Theatre in March 2009, days after its release, to a half-filled room of cowboys and cowgirls, and she was already flicking her curls dramatically like a stadium star (which, admittedly, in America she legitimately was). In such tight confines, it was jarring; you wanted to yell out “Take it easy, Taylor!” But by the time she got to Love Story, I’m sure I was flicking my hair just as feverishly.

The relationships: This was Taylor’s first foray into tabloid territory, the point where fans and gossip rags started poring over her lyric book for clues behind Last Kiss, Better Than Revenge and Forever & Always, a wonderfully conflicted stomper inspired by her split from Joe Jonas (who famously broke up with her in a 25-second phone call).

More significantly, this was the start of Taylor as cultural molotov, a figure discussed not just for her music but the rest of it. It was in September 2009, while accepting the award for best female video for You Belong with Me, that Kanye (“Imma let you finish”) interrupted Swift’s speech at the MTV VMAs, sparking a narrative that enveloped her career for years to come.

The moment: Taylor’s “monologue song” on Saturday Night Live from her hosting debut in November 2009. Summing up her approach to publicity, she castigated Joe Jonas, confirmed she was “dating the werewolf from Twilight” (Taylor Lautner), and teased Kanye. As one incisive YouTube commentator notes: “Reputation actually started here but no one realised.” RM

2: Reputation (2017)

Taylor Swift could not come to the phone during her Reputation era.Credit: AP

The music: Reputation remains by far Taylor’s most innovative and unexpected outlier, a defiant heel-turn after the massive success of 1989 led to a public backlash – of #SquadGoals and the extravagant lifestyle she flaunted on Instagram; of the Famous incident with Kanye and Kim Kardashian, which suggested Swift’s sweet image was fake and calculated – that turned Swift into a lightning rod for debates about racism and privilege (and Trump) and forced the singer to retreat from the spotlight.

Reuniting with pop producers Max Martin and Shellback for an album heavily inspired by hiphop and R&B, Reputation divided fans and critics with its brash, provocative content and sonic departure. But it’s been reappraised in recent years because the songs are among Swift’s best – sexy, bitter, fun, flirtatious, winking, dark – including some lump-in-throat moments (namely Delicate, Dress, and Call It What You Want) where Taylor’s despair and defiance are stark.

The aesthetic: This is snakes and leathers Taylor, the femme fatale Taylor, the “they’re burning all the witches even if you aren’t one… so light me up!” Taylor. How could anyone not love this Taylor?

The relationships: You have to nod to Kanye and Kim here, considering the public narrative twisted so far in their favour during this era. I’m no Gaylor authority, but the heavy yearning and unrequited love of Gorgeous, Getaway Car and Dancing With Our Hands Tied seem like peak Karlie Kloss evidence.

But the main figure, again, is Joe Alwyn. The pair met at the Met Gala in 2016 even though news of their romance didn’t break until the following year; it gives songs like Delicate (“This ain’t for the best/ my reputation’s never been worse so/ you must like me for me”) an emotional edge, Taylor finding love in a hopeless place.

The moment: “Sorry, the old Taylor can’t come to the phone now. Why? Oh, ’cause she’s dead.” RM

1: 1989 (2014)

Taylor Swift in our favourite era, 1989.Credit: Getty

The music: “My name is Taylor and I was born in 1989.” Swift’s 2014 album marked the point where she became a bona fide pop star. It was the first Swift record that her by now-frequent collaborator, producer Jack Antonoff, worked on – those are his fingerprints all over Out of the Woods, I Wish You Would and deluxe bonus track You Are In Love. That Antonoff sound would go on to be synonymous with Swift’s music, and he would go on to be one of the most coveted pop producers in the world.

Earworms abound on this record – Style, New Romantics, Blank Space – and some new sounds, too (the Lana Del Rey inspiration is strong on Wildest Dreams, and the two collaborated later on Midnights). Swift again took swipes at the media’s portrayal of her; Blank Space sends up the seductress that the press made her out to be. In this way, it’s a continuation of the self-determination that she began on Speak Now.

The aesthetic: The look for this era is nighttime glam – sequins, glitter and anything that would make you sparkle on the dance floor. And don’t forget the iconic red lips.

The relationships: This was when Swift’s “squad” was cemented – the singer was often spotted with a group of high-profile friends including Karlie Kloss, Gigi Hadid, Lena Dunham, Cara Delevingne and Selena Gomez, all of whom starred in the video for Bad Blood. Also, 1989 was released right after Swift’s brief yet iconic relationship with Harry Styles ended, the coupling that set Tumblr blogs alight.

The moment: With the Australian leg of Swift’s Eras tour set to begin, it would be remiss not to mention the time when she created a loop of herself screaming the word “Sydney!” during her 1989 world tour, while harmonising with herself. Swifties have a whole list of chants for her shows, and this one has special local resonance. Will we get a reprise? GN

Taylor Swift’s Eras Tour is in Melbourne from February 16-18 and in Sydney from February 23-26.

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