Where it all began How Taylor Swift’s debut single has defined 20 years of her pop stardom – video Released 20 years ago, Taylor Swift’s debut single is, on the surface, a tribute to the power of music, and about how hearing a song by your favourite artist can send you back to the memories associated with first hearing it. She named Tim McGraw after one of her favourite country singers, with a sentiment aimed at a former boyfriend who had left her behind: “When you think Tim McGraw,” she sang, “I hope you think of me.” The power of Swift’s songwriting and the immediate force of her presence as a pop star mean that that is what most of us think when we think Tim McGraw. From day one, we could see Swift’s power to remake culture in her own image, a talent that has – two decades on – made her one of history’s biggest pop stars. The sleek 36-year-old showgirl we know today may seem a million miles from that country teen with her corkscrew curls and cowboy boots. But if you look past the slightly hokey southern twang on her debut single, that song contains almost everything we know about Swift as an artist today. The fundamentals are there: no 21st-century pop star has written about romance better, and she conjures her setting with what would become her trademark intimate detail – the “little black dress” that would make way for that scarf she left at an ex’s sister’s house; the moon on the lake that foreshadowed all the kissing in the rain; the cars parked down back roads where the young couple had secret trysts lit the way for hitting the brakes too soon. But we can also see her assured sense of rewriting tired narratives. From the first line, when she recalls her lover telling her “the way my blue eyes shined put those Georgia stars to shame”, she tells him: “That’s a lie.” Swift knows she tells better stories than everyone else. From day one, she also knew the power of being the person who gets to tell the story. Here she rewrote small-town southern romance; years later she undid the man-eater archetype on Blank Space and gave life to the spectre of the “mad” woman on The Last Great American Dynasty. In Tim McGraw, once the guy has left, she writes him a letter that tells him how he should think about their time together, and leaves it on his doorstep – the bold author of her own fate. He may have gone, but in extremely Swiftian form, it’s her who is having the last word: the foes who would later inspire songs such as Mean, Bad Blood and Look What You Made Me Do never stood a chance. She also knows how to make time work for her, backflipping around the chronology of their relationship – from past memories to present pain to future nostalgia – to take complete narrative control of a situation. You might hear a song from your past and get a vague warm, fuzzy feeling. Swift is a beautiful freak who remembers it from every angle, all too well. From the beginning, Swift showed us exactly who she was, revealing the innate focus that helped create the defining pop songs of our time – as well as a career that wrote her into legend, making her the lens through which we understand so much of pop, pop culture, womanhood, the music industry, and much, much more. Here are the 20 ways she remade the world in her own image. Laura Snapes Image credits: Jeff Kravitz/FilmMagic; Big Machine Records She escaped growing pains Growing pains have always been a rite of passage for teen-girl pop stars – as much as the No 1 singles and big-budget videos. In a more manufactured era, obsolescence was built in: inevitably you would rebel against the system that controlled you, and, inevitably, it would spit you out. Swift understood that maintaining control would protect her. She knew that writing her own songs would create an authentic personal relationship with fans – one that she assiduously deepened IRL – that no label would dare mess with. From 2008, when she released her second album, Fearless, her management became a family business. Being the flagship success of a small label, Big Machine, also gave her the agency to grow on her own terms; label head Scott Borchetta even encouraged it, suggesting that 2010’s biting Speak Now shouldn’t be named Enchanted, after a lovestruck song of the same name, because she was no longer writing about “fairytales and high school”. Every corkscrew curl, princess dress and bowler hat was her own choice; she marked her growth in her genre evolution, from country to emo to sleek pop. As she said in 2015: “As far as the need to rebel against the idea of you, or the image of you: like, I feel no need to burn down the house I built by hand. I can make additions to it. I can redecorate. But I built this.” You could argue it came at a cost. Interviews with the teenage Swift reveal someone acutely aware of the price of stepping out of line: in high school, she characterised her refusal to party as a choice “between being popular or not messing my life up”; she didn’t drink until she turned 21 (“I knew I couldn’t get away with it until then”) and knew that after you mess up once, “people are going to be waiting for you to mess up again”. In 2009, one profile writer noted: “Self-preservation is one of Swift’s favourite phrases.” Several of the older, unreleased songs she resurfaced as the bonus “From the Vault” tracks on her Taylor’s Version re-recordings dwelled on her anxiety about being replaced by younger models. That level of control and perfection is just as unsustainable as, say, pretences over Britney’s virginity; you could see how it may have contributed to the disordered eating Swift experienced in the mid-2010s, and how unbearable it would have been when she lost control of the narrative for a few years around then. Yet, Swift made it to young adulthood without directly creating scandal or revolt. You suspect her unmatched polish may have sent the press, as her ingenue status faded, searching for any stick to beat her with and coming up with ... her very normal boyfriend count. The pathetic nature of those charges underscored a rigged game no amount of perfection could beat – but Swift got further than most, and opened up a slipstream for her successors to self-define. LS Image credits: Ethan Miller/Getty Images She made the traditional vanguard Max Martin and Jack Antonoff. If you want to understand Swift, just think about Apple – yes, the computer company. Apple, famously, has rarely invented anything. Its reputation for quality, intuitive products has almost made it anti-innovation; when gizmos such as touchscreen smartphones or tablets were first introduced to the market, Apple didn’t rush to release its own competitor. Instead, it waited until said products were familiar, and then released best-in-class versions. Swift works in a similar fashion. She tends to change slowly. When it comes to producers, she started out working with Nashville stalwart Nathan Chapman before making a few songs on her 2012 album, Red, with Max Martin and Shellback, two of the era’s super-producers: together they incorporated tinny synths and light dubstep drops, the sound du jour of a few years earlier. On 2014’s 1989, she worked mostly with Martin and Shellback, but made a few songs with Jack Antonoff, a then-unknown who had notched a megahit, We Are Young, with his band Fun a few years earlier. In 2017, Reputation was another Antonoff/Martin and Shellback split, but on songs such as Ready for It and I Did Something Bad, she essentially presented a more mainstream-friendly version of the harsh electro sound that her then-nemesis Kanye West, now Ye, had worked with on his culture-shifting 2013 record Yeezus. Versions of this story recur throughout Swift’s career. With each record, she almost always inches her sound forward, but she’s rarely, if ever, the first to work with a new face or a new style. This is, in many ways, an inversion of how pop stars as big as Swift used to work. Madonna and Michael Jackson – two of the only musicians who have ever achieved the same level of cultural saturation and interest – tended to look to the underground for inspiration, in terms of music, fashion and aesthetics, and make those underground styles commercially viable. (Think Madonna turning the ballroom culture that her backing dancers came from into Vogue, one of her most indelible hits.) Swift’s strategy is deeply reflective of her time: one in which it pays to be risk-averse and give the people exactly what they want, when they want it. Shaad D’Souza Image credits: Matt Sayles, Invision/AP She reclaimed cringe In the run-up to the 2020 US election, an entire news cycle was dedicated to speculating on whether Swift would endorse a presidential candidate. She confirmed her support of Joe Biden and Kamala Harris in the cutesiest way possible: with a tray of homemade cookies. Swift is cringe, but she is free: self-directing corny videos, selling references from her own songs – cardigans and red scarves – as merch, hosting fan parties at her house and writing the worst Instagram captions known to mankind. (She saved one of the most groan-inducing for her engagement announcement, writing: “Your English teacher and your gym teacher are getting married.”) And while it feels incongruous for Swift, a noted fan of a sourdough starter, to make “wine moms” the butt of the joke in songs, perhaps it only adds to her bona fides: there’s nothing cringier than a lack of self-awareness. Owen Myers Image credits: Instagram/taylorswift; Startraks/REX/Shutterstock She made competency a flex While Swift’s songs are full of wayward emotions, she runs her career with military precision. As a kid, when her friends were watching the Disney Channel, she studied episodes of VH1’s Behind the Music and deduced that artists went off the rails when “they lost their level of self-awareness”. It made her hawkish about ambition and execution: as a teenager, she outwitted Nashville stalwarts, challenging them on industry norms and understanding exactly how to play the game to get ahead. When she was criticised for her singing or dancing, she skilled up. When foes came for her, she wised up: “I got smarter, I got harder in the nick of time,” as she sang on Look What You Made Me Do. From big-picture concepts to the finest details, Swift is a one-woman panopticon on her own career. Of course, all-encompassing professional excellence is also a very Beyoncé trait – but she doesn’t show her hand the same way. Swift wrote the 21st-century playbook on elite pop stardom, and she wants us to know it. LS Image credits: Gareth Cattermole/TAS24/Getty Images for TAS Rights Management She bent formats to her will Swift understands streaming better than almost any of her contemporaries. Although she was late to warm to the format, in the 2020s she has proved herself a master of the form: deluxe editions of 2022’s Midnights and 2024’s The Tortured Poets Department, each essentially doubling their length, were released mere hours after the originals. Streaming is a volume game when it comes to breaking records; adding tracks in this way encourages repeat listens, without the threat of fans getting tired or bored. And it’s an extremely linear medium: Tortured Poets and The Life of a Showgirl each had their single placed as track one, so that it would notch up the most consumption and become the default hit. When it comes to understanding format – and how format relates to commercial dominance – Swift has long been ahead of the curve. Among pop stars, she popularised the practice of selling vinyl records with exclusive covers in order to boost chart positions, previously only the purview of superstar rappers. CD copies of her 2019 album Lover came with an exclusive notebook containing snippets of her own personal diaries – but fans had to buy four copies in order to read all the pages. (Similarly, Reputation’s CDs came with one of two exclusive magazines, and 1989’s deluxe edition came with a randomised set of Polaroid-style photos.) Swift was savvy with format early in her career, too. In seeming acknowledgment of the fact that country has a far bigger audience in the US than overseas, she bundled international editions of her 2008 breakthrough album Fearless with singles from her debut, while certain songs from 2010’s Speak Now were redone with pop mixes for the international market. She also seemingly took to heart the advertising industry adage to meet your customer where they are, selling copies of her fourth album Red at Papa John’s pizzerias. Of course, all of this paled in comparison to Taylor’s Versions, her monumental album re-recording project, which allowed her to reactivate older music in her catalogue and re-market it to new fans. The re-recorded albums also included new, previously unreleased songs, doubly incentivising existing fans to repurchase copies of albums they already owned. In the years since Swift began releasing the Taylor’s Versions, other artists in dire contract situations, such as JoJo, have followed suit, while some have simply done it for fun: Hilary Duff packaged her new album with new recordings of hits such as Come Clean. In essence, Swift turned what was once seen as a desperate business move into a shrewd marketing play. SDS Image credits: Jane Barlow/PA She set new melodic standards Gracie Abrams, Maisie Peters and Holly Humberstone. Once you know about the T-Drop , you’ll start noticing it everywhere. The Switched on Pop podcast hosts coined this term to describe Swift’s penchant for dropping into her lower register without warning to give a sly sting in the tail to her melodies, particularly when they are already dripping with sarcasm. See her deliciously drawn-out delivery of “drunk and grumbling on about how I ... can’t ... sing ” in Mean . Her acolytes love to use the T-drop as a vehicle for their ultra-specific, highly Swiftian imagery, and drippy recent hits from Gracie Abrams, Maisie Peters and Holly Humberstone (pictured) hinge on the device. These singers get Swift’s emotion but not her knack for goofy – instantly memorable – imagery that is a little odd, or downright off: “Sexy baby”, “grinning like a devil”, hell, even “this sick beat”. OM Image credits: Ian West/PA; Roy Rochlin; Viktor Szymanowicz/Anadolu via Getty Images She made game day for the girls On 24 September 2023, Swift attended her first ever Kansas City Chiefs game in support of her beau, star tight end Travis Kelce . “It’s like these two cultural titans – the NFL and Taylor Swift – were coming together,” says Bryan Graham, the Guardian’s deputy US sports editor. Swift was no longer on the bleachers, but firmly in the executive suite of stadiums, marking what Ella Brockway, assistant US sports editor, calls “a different level of celebrity in sports to what we’ve seen before”. Swift’s entry into the NFL world may have been due to love, but it also didn’t hurt that it came with the opportunity for personal brand expansion. OM What does Taylor Swift mean to the NFL ? BG F
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