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Ten Years of Taylor Swift: How the Pop Star Went From Sweetheart to Snake (and Back Again?)

In 2009, Taylor Swift was a country music princess on the verge of superstardom. In 2019, she’s a full-blown music juggernaut, and a case study for the ups and downs of modern pop stardom.

Daniel Zalkus Illustration

In the same way that a meteorologist might struggle to predict a whole year’s weather rather than the next week’s rain, it is exceedingly difficult to distill an accurate assessment of Taylor Swift as though she’s an ordinary pop act; she is a musical biosphere unto herself. Swift’s music isn’t released as much as it is unleashed, the melodies saturating deep into the tissue of contemporary public life whether we like it or not. I turn on the television to watch sports and Taylor Swift is there; I go to pick up an Amazon package and her blond, feline face is smiling at me and reminding me I’m absolutely going to listen to her new album, Lover, of course I am, how could I not? Swift has achieved the kind of success that turns a person into an institution, into an inevitability.

But before she felt as inescapable as the weather, she was simply a star in waiting. Ten years ago, Taylor Swift was a 19-year-old Nashville singer-songwriter with a steadily growing fan base, a pair of twangy tween-dream albums and a string of Billboard hits. But 2009 was the year her perky, countrified celebrity solidified into industrial-grade American fame.

It was the year “You Belong With Me,” an earworm about an underdog-in-love that helped turn its girl-next-door singer into the closest thing music had to a Disney princess, blasted from car radios no matter which station they were turned to. Swift’s second album, Fearless, had made her the best-selling musical act in the United States. Critics loved that she wrote her own songs, parents loved that none of them had cusses, and everyone loved that they were catchy as shit. Swift was also a publicity prodigy, connecting with fans on MySpace and with tabloid-reading, album-buying moms through her Us Weekly–core romance with Disney star Joe Jonas. She hosted Saturday Night Live for the first time. And at the MTV Video Music Awards that year, Kanye West jumped onstage to interrupt Swift’s acceptance speech for Best Female Video, kicking off an exhausting entanglement that would alternately muddle and enhance each artist’s reputation. (What else fuels fame like a feud between celebrities?)

In the ensuing decade, Swift has risen into a rarefied echelon of true pop superstars, though her sweetheart persona has been complicated to the point that her formerly shiny-smooth image now features snakeskin embellishments. She doesn’t cry about her haters anymore, she uses them as fodder for hit-single cheek—“Shake It Off,” “Look What You Made Me Do,” “You Need to Calm Down.” Her best-selling record is still 2008’s Fearless, released just one month after Spotify showed up in the United States and nuked album sales indefinitely, but Swift has dealt with that decline by making sure her tours are treated as unmissable spectacles by fans. Her hefty album sales for the Reputation tour in 2018 led Forbes to crown her the highest-paid celebrity in America. As touring profit becomes a more reliable indicator of appeal, Swift is still on top even if she never bests her teenage self’s album numbers. “Her core fan base is still huge,” David Turner, a music critic who runs the streaming music newsletter Penny Fractions, told The Ringer. “But she doesn’t seem just fine with having a core fan base. She might just want too much out of what is a very fleeting and hard-to-maintain existence.”

This week, Taylor Swift is releasing her seventh studio album, Lover, after an old-fashioned Big Album Rollout that feels a little stuffy and out of step in an era when Ariana Grande can release Thank U, Next on an inspired whim and Beyoncé’s strategy for domination involves blitzing fans with new music. Lover is on track to sell well, with “approaching” 1 million copies sold prior to release, according to a Variety report, although the mixed critical reaction to her first singles suggest that the days of Swift as an unmitigated darling are officially over. (And the Variety report is based on a fuzzy international prerelease tally.) Swift hasn’t been a genuine ingenue for a long time—but it’s not entirely clear what she is now, or whether her position in pop is sustainable.

The fact that Swift was a real-life precocious teen when she came onto the scene is important to understanding her early public image. Swift had started playing guitar and writing music as a child, gaining attention by singing the national anthem at local sporting events in the early aughts. Raised in Pennsylvania, Swift’s parents moved her to Nashville to further her career; her Southern twang reflected her ambition more than her upbringing. She signed her first record deal at 14, negotiating with former Universal executive Scott Borchetta at Big Machine Records. “Taylor and I made an aggressive deal on the back end,” Borchetta told Rolling Stone in 2009. “I’ve written her some very big checks.” The wunderkind with finance-whiz parents was shrewd from the start, and not just on the business side: Piggybacking off Tim McGraw’s celebrity to drum up interest in “Tim McGraw” gave country fans an easy way to remember Swift as the girl who sang about their icon. In a glowing early profile, The New Yorker called her a “preternaturally skilled student of established values.” She hewed closely to the tried-and-true girlie-girl Nashville aesthetic for female talent while quietly exerting an unusual amount of creative control; unlike other young stars, she wrote or cowrote almost all of her music. She was perfect at being conventional—so perfect that nobody felt threatened by the deftness of her songwriting.

Swift at the Country Music Awards in 2008
Getty Images

Swift’s age and background meant that she could cultivate the image of a bubblegum-country cherub fairly easily. Just by existing, she checked so many boxes: in addition to being extremely young, she was blond, white, wealthy, and thin. On top of that, she liked to strum her guitar in poufy outfits, to sing her own longing lyrics about backyard romance, and to giggle and go along with whatever her interviewers wanted, crafting her goody-two-cowboy-boots image like a pro. “The young country super-starlet is a flat-out fantastic interview subject. So open and honest and funny and interesting; so willing to play along—to go here, there or anywhere during the course of an interview,” J. Freedom du Lac wrote in a Washington Post profile from 2008. “She’s a reporter’s dream—and, no doubt, a publicist’s, too. A media darling, indeed.”

Swift was also a digital native who knew how to use social media in a way that Nashville hadn’t seen yet, still quite novel for pop acts. “She has aggressively used online social networks to stay connected with her young audience in a way that, while typical for rock and hip-hop artists, is proving to be revolutionary in country music,” The New York Times’ Jon Caramanica noted in 2008—the same year 13-year-old Justin Bieber signed with Scooter Braun after uploading a video of himself singing to YouTube.

Swift worked in a confessional mode, and part of her widespread appeal was how flung-open her emotions appeared; if you hurt her, she wrote about the ways you hurt her, and then sprinkled her liner notes with hints as if to whisper: Yes, I was referring to you. This intimate approach built a legion of devoted, empathetic fans, but also shoehorned Swift into the limiting role of the easily bruised naif. And despite her excellent reception, she often grabbed headlines for being a whiz kid; her breezy, deft confessional narratives were sometimes categorized as teenybopper alchemy, which was something Swift pushed back on from the beginning. “I didn’t want to just be another girl singer. I wanted there to be something that set me apart,” Swift told Entertainment Weekly in 2007. “And I knew that had to be my writing.”

And then it happened. At the MTV Video Music Awards in September 2009, Swift won the Best Female Video award for “You Belong With Me,” beating Beyoncé’s “Single Ladies” video. As Swift spoke, a Hennessy-soaked Kanye West catapulted himself to the stage and grabbed the microphone from her hand. “Yo, Taylor, I’m really happy for you, I’mma let you finish, but Beyoncé has one of the best videos of all time,” West said. “One of the best videos of all time!”

West was escorted out of the building as Beyoncé grimaced in the crowd and Swift fled offstage to sob. It was actual chaos in a show meant to simulate shock, a grab-your-fucking-popcorn moment MTV couldn’t have manufactured if it tried. It didn’t matter that Kanye was trying to prove a valid point about race and awards shows—that he had gone about trying to make his point in such an abrasive fashion, and hurt the feelings of a pretty, white teen star who had done nothing wrong overshadowed everything else. Swift was despondent. Kanye’s clearly dashed-off blog post apology didn’t improve matters. (“I’M SOOOOO SORRY TO TAYLOR SWIFT AND HER FANS AND HER MOM,” it begins, before reaffirming that the Beyoncé video was, indeed, superior.)

The incident initially provided Swift with a major swell of positive PR. The media took her side; President Obama called West a “jackass” shortly thereafter. “In the arc of her career, it will be seen as, ironically, one of the reasons why she became what she became,” Elaine Lui, the founder of celebrity and pop culture analysis website Lainey Gossip, told The Ringer.

Even more important than goodwill, the moment moved records, something her camp openly admitted. “The Kanye incident brought attention to Taylor, to an audience that did not really know her or her music,” Borchetta told The Wall Street Journal in 2010. “And when they did check it out, they discovered that they really liked it.” Ever canny, Swift released “Innocent” in 2010, an impressively patronizing song about the experience that suggests Kanye is too simple to actually be a bad person, taking full advantage of her positioning as a wronged party. (“Thirty-two and still growin’ up now / Who you are is not what you did.”) She performed it at the next VMAs. During the same show, Kanye performed “Runaway” and had his own moment of redemption, giving a “toast for the assholes” to a rapturous crowd. The intertwined artists had each found a way to turn the incident into music. Swift had officially been introduced to most of America. Her next move was domination.

Swift got a true fairy-tale awards show moment the next year, in 2010, when she became the first solo female country act to win the Grammy for Album of the Year for Fearless. She kept a regimented schedule, releasing an album every two years—Speak Now in 2010, and her fourth album, Red, in 2012. Both debuted at no. 1, solidifying Swift’s position as a music-industry force, gobbling up Grammys and breaking sales records. A country star who, to that point, had shed every marker of the distinction aside from her sound, she began openly flirting with pop, working with producers like Max Martin and Shellback (“We Are Never Ever Getting Back Together,” “22”), and collaborating with Ed Sheeran and Snow Patrol’s Gary Lightbody.

Since her Joe Jonas days, Swift had gravitated toward famous romantic partners, a habit she kept as the years went on, her increasing fame—and the increasing fame of her boyfriends—making her a constant presence in tabloids. Starting with Taylor Lautner in 2009, Swift’s publicly documented relationships over the next few years included John Mayer, Jake Gyllenhaal, and Harry Styles. In addition to keeping her on the front page of supermarket rags, these relationships often resulted in hit singles, like “Dear John” and “We Are Never Ever Getting Back Together,” reportedly about Mayer and Gyllenhaal respectively. (The Easter eggs she left in her liner notes, like capitalized letters spelling out words or acronyms hinting at who each song was about, played into the curiosity around her delectably passive-aggressive lyricism.) Even people who didn’t listen to her music, then, were made aware of her status as a queen bee in the A-list dating pool. And though present in the tabloids for her romantic life, Swift managed to keep her image squeaky clean; while slightly older peers like Lindsay Lohan and Britney Spears were publicly struggling through substance use issues and photographed in embarrassing and dangerous situations, the closest Swift got to a scandal was dating an 18-year-old Kennedy scion and making her neighbors angry for … digging up rocks. In 2012, Michelle Obama presented her Nickelodeon’s Big Help Award. “This is amazing!” Swift gushed, shaking the first lady’s hand.

Swift’s appearances in the public eye continued to frequently involve a moment when she looked awestruck, surprised, and generally in need of a hug. She was “absolutely traumatized” by Justin Bieber’s Punk’d punk. Her awards-show face became a meme. She fell so easily into her groove as America’s flabbergasted sweetheart that it started to irritate people, but the music was good enough and the public goodwill strong enough that nobody cared that much. Or, almost nobody. Deadspin published something literally called “The Hater’s Guide to Taylor Swift” in 2010, with the words “This Woman Must Be STOPPED” superimposed over photos of Swift as accompanying art. And in 2012, Salon, in perhaps its most Salon moment to date, argued that Swift was overrated because people had lowered their expectations for life after the recession. But these were contrarian provocations, and in general, Swift had reached an ascendant point in her career and public image.

By 2014, Swift was the most popular country-music act in the world, but not yet the most popular music act in the world. And so she released 1989, her first true front-to-back pop album, with synthesizers and programmed percussion supplanting her acoustic guitar, largely produced by Max Martin as well as Lena Dunham’s ex-boyfriend Jack Antonoff. It was a pop blockbuster, with songs so polished and precision-engineered for Top 40 it seemed like Swift had consulted some demonic algorithm developed to lodge a song in the brain forever, to get it played at football games, bat mitzvahs, and weddings as well as rodeos. “A lot of people who couldn’t get over the country part of her were finally listening to her,” Rolling Stone critic Brittany Spanos said. While the country music market still had a robust album-buying culture and had its own touring circuits and Nashville darlings, working within a genre pigeonholed Swift, even if she was clearly producing music that felt as much pop as country on Red. Although some country fans felt betrayed, the positioning of 1989 as Swift’s big transition allowed her access to a new market and announced that she wanted the whole market. Despite a sharp industrywide decrease in record sales, 1989 was a massive success, exceeding commercial expectations by hitting 5 million U.S. sales in its 36th week of release, making it the fastest-selling album in a decade and ginning up the best reviews of Swift’s life. “It remains her masterpiece, her strongest piece of work,” Lui said. “It was a firm demarcation between Taylor the country music star and Taylor the global pop star and cultural phenomenon.”

“Welcome to New York,” the album’s first song, signaled a shift in Swift’s personal life, as she had left Nashville and moved into a vast penthouse in Tribeca. She began gathering famous female pals with gusto, embarking on high-profile friendships with Lena Dunham, Lorde, and a wide range of narrow models, most notably Karlie Kloss. (Swift’s devotion to Kloss inspired a very robust online community of “Kaylor” fans to theorize and fantasize about the possibility of a romantic relationship between the two.) While her romantic life had served as Swift’s path into the tabloids, now her roster of preposterously hot friends, known as her “squad,” served that function. “I think that I just decided if [the media] was going to say that about me, that I was boy-crazy and so dependent on men and all that, I wasn’t going to give them a reason to say that anymore, and I wasn’t going to be seen around any men for years—so that’s what I did,” Swift told Vanity Fair, in an interview where she raved about texting her “20-25” closest friends every day.

Also in 2014, Swift severed ties with her longtime PR team and hired a publicist named Tree Paine, a former Warner Music Nashville PR executive who started her own firm when she signed Swift. Paine’s entrance into Swift’s life marked a turning point in her availability to the press. After Paine’s hiring, Swift’s tendency to gab about her personal life with reporters petered out. (Paine did not respond to a request for comment for this story.)

Instead, as her star power continued to grow, Swift occasionally used both the media and social media to advocate for the payment of artists. In 2014, she explained her decision to pull her music from Spotify in a Wall Street Journal op-ed, saying she did not believe the platform fairly compensated artists. In the summer of 2015, she used Tumblr to lambast Apple for not paying artists for the streams of their work that customers played during their free trials, which then caused Apple to nearly immediately capitulate. (So immediately, in fact, that it stirred up theories of a secret arrangement between Swift and Apple.) While she remained conspicuously unwilling to discuss politics, her eagerness to shape the conversation about artists’ rights underlined that when she wanted to, Swift had enough star wattage to alter the contours of the entire industry.

Swift had always enjoyed largely critical reception as well as commercial success—The New York Times, for instance, had always been in her corner—but during the 1989 album she created her first major controversy with the “Shake It Off” video, which features a number of different dance styles, including black dancers twerking. Although white dancers were also twerking, the close-up shots of black bodies coupled with the fact that all of the ballerinas dancing were white led to headlines like “Is Taylor Swift’s Shake It Off Video Racist?” and a Twitter dress-down from rapper Earl Sweatshirt.

During the same album cycle, Swift pointedly highlighted herself as someone who had been on the receiving end of gendered criticism. “For a female to write about her feelings, and then be portrayed as some clingy, insane, desperate girlfriend … that’s turning it into something that is, frankly, a little sexist,” she told Vanity Fair. She shared a quote from Madeleine Albright—“there’s a special place in hell for women who don’t help other women”—to comment on a quip Tina Fey and Amy Poehler had made about her dating life at the 2013 Golden Globes. Invoking feminism was, like most Swift moves, a prudent shield. However, more cracks in Swift’s meticulously constructed persona were about to appear.

2016 was a bad year for America, and a notably not-so-good year for Swift; declaring oneself a feminist was no longer a bold action for a pop star. She was between albums, yet her purposefully high-profile life kept her in the public eye. She had received a constant stream of attention for the A-list guest stars she brought out during her 1989 tour, like Ellen DeGeneres, Lorde, and Mick Jagger, and coupled with the heavy media coverage of her famous friendships, Swift’s inescapable daily presence in the news cycle began to grate. “The squad stuff had taken over. Everything she did was a story,” Spanos said. “Which also leads to overexposure.” This was something Swift, ever self-aware, was proactively trying to prevent. “I think people might need a break from me,” she told NME the previous year. Perhaps she could sense what was coming.

Swift with Hailee Steinfeld, Lily Aldridge, Gigi Hadid, and Lena Dunham during the 1989 Tour in 2015

Swift hadn’t previously been immune to criticism, exactly—in addition to the critiques of her “Shake It Off” video imagery, her video for “Wildest Dreams,” set in colonized Africa, had received blowback for its creepy daydream of colonialism. In 2015, writer Dayna Evans argued that Swift’s brand of feminism was performative and ultimately hollow. “Swift has to be the person with the prettiest friends, the biggest records, the most popular and successful and groanworthily obvious boyfriend,” Evans wrote in a piece titled “Taylor Swift Is Not Your Friend.” “The underdog narrative that the Swift machine has built is one of forced falsehoods; Swift is not coming from behind. She’s been ahead since she started.” And when Swift inserted herself into a conversation Nicki Minaj was having on Twitter about racism at awards shows, she appeared both self-centered and blithely unaware of the larger issue of racism in the industry at play. (The two stars quickly made up.)

That was all a prelude to the real backlash, which began when Kanye West reentered the picture. The two had publicly made nice the previous year at the Grammys as well as the VMAs, when Swift presented West an award, and West told Ryan Seacrest that they had even considered collaboration. West also sent Swift a square made of flowers, which she Instagrammed. But the détente fell apart in 2016. That February, West released the song “Famous,” which includes the following lyrics: “I feel like me and Taylor might still have sex / Why? I made that bitch famous.” Swift was, famously, not happy.

“Taylor was never made aware of the actual lyric, ‘I made that bitch famous,’” her representation told Entertainment Weekly. And when Swift won Album of the Year in 2016 later that month, she appeared to upbraid West during her speech. “There are going to be people along the way who will try to undercut your success or take credit for your accomplishments or your fame,” she said. Kanye insisted that she had approved the lyrics. “She had two seconds to be cool and she fucked up,” West said during a club appearance. That June, Kim Kardashian West insisted to GQ that Kanye had received permission—and subsequently released on Snapchat a recording of Swift verbally approving the song and thanking West for calling her. “Relationships are more important than punch lines,” West said on the call, emphasizing that he wanted to make sure Swift felt comfortable with being name-dropped. “Right after the song comes out I’m gonna be on a Grammy red carpet and they’re gonna ask me about it and I’m gonna be like, he called me,” Swift assured him.

Reputational hell broke loose for Swift; #KimExposedTaylorSwift rapidly began trending on social media; a proliferation of the snake emoji, meant to symbolize Swift’s untrustworthy and low nature, checked the comments of her Instagram page and the mentions of her Twitter. “I would very much like to be excluded from this narrative,” Swift wrote in a now-deleted Instagram post.

Victimhood at the hands of West was a narrative Swift had often stoked and benefited from. Now, though, she was in too deep—her alleged machinations had been exposed. “The Kimye thing was probably the most general public disdain for her,” Spanos said. “She wanted to play the victim,” Kim said during the episode of Keeping Up With the Kardashians that preceded the leak of the recording on Snapchat. “It worked so well for her first time.”

It was Swift’s worst PR moment, undermining the persona Swift used to connect with fans, a persona founded on a sense of struggle against bullies. “This really subverted that narrative and showed that she was just as calculating as some of these people that she had been accusing of being calculating and manipulative,” writer Allie Jones, who covers celebrity culture, told The Ringer. Jones noted that Swift’s impulse to amp up her public displays of affection with then-boyfriend Tom Hiddleston didn’t help the situation. “People pretty quickly figured out that that was also calculated because paparazzi don’t just hang out near her private home in Rhode Island, hoping to catch her with a random British actor.”

In addition to her renewed feud with Kanye and much-paparazzi’d relationship making her appear manipulative, Swift also faced blowback for her silence on the presidential election. Katy Perry—another supposed bully Swift rallied against in the 2014 song “Bad Blood”—was touring the country as part of Hillary Clinton’s campaign, and nearly every other major pop star had explicitly come out in support of Clinton, from Beyoncé to Demi Lovato. Swift, however, did not. Her silence was taken as a political statement, and some fans horrified by the candidacy and election of Donald Trump fumed about Swift’s silence. “Taylor Swift, much like Chance the Rapper and Katy Perry and a number of other artists of that era, existed in a wave of post-Bush, Obama-era positivity,” Turner said. “I don’t know how you make that pivot.”

Swift had always, of course, been a rich white girl “from Nashville,” but she’d mostly been able to position herself as a politically neutral figure during the Obama era. But in an election as contentious as 2016, silence was its own statement, an announcement of privilege too loud to ignore. “She is maybe our whitest pop star,” Spanos said. “She’s kind of existed in her own bubble.” Swift had been able to use this whiteness to her advantage on many occasions; most notably, the optics of the angry black man attacking the shaken blond girl had played in her favor during the 2009 VMAs incident. And although Swift would eventually come out in support of Democrats, her often-noted silence during the 2016 presidential campaign made her into an unwilling symbol of complacency and right-wing sympathy. White supremacists praised her online as an “Aryan goddess.” Her studiously anodyne persona had been turned on its head.

In the fall of 2017, Swift teased the release of Reputation with images of snakes, signaling that she intended to address the Kimye debacle and her tarnished image. Swift had mined hits from her intrapersonal conflicts in the past, so continuing the tradition made sense. However, the album’s lead single, the surly electro-pop kiss-off “Look What You Made Me Do,” fell flat with some critics. Vulture called it “the worst music of her career.” The Ringer’s Lindsey Zoladz referred to it as “boring, unrelatable, and insular,” and our own Justin Charity called it “a failure.” (Personally, I think it’s a great workout track for daydreaming about emotionally destroying your enemies by obtaining glorious abs.)

Media ill will remained so pitched that Swift’s inclusion in a Time magazine feature on women in the #MeToo movement prompted a debate over her worthiness, even though she had filed and won a lawsuit against a DJ who had groped her as a young woman, speaking out in unflinching terms about the issue. The cold feelings went both ways; instead of sitting for traditional interviews, Swift published a poem in UK Vogue and a list of things she “learned before turning 30” for Elle.

However, the lackluster critical response to “Look What You Made Me Do” didn’t lead to a drubbing when the album came out; as an album, Reputation still received largely positive reviews praising many of its other songs. “End Game,” a collaboration with Ed Sheeran and Future, sounded like an impressively bad idea in theory but turned out surprisingly fun, and the sixth single, “Delicate,” is one of Swift’s finest songs. While the lead singles spent less time on the charts than her one-two 1989 punch of “Shake It Off” and “Blank Space,” “Delicate” ended up as a sleeper hit. It is actually the longest-charting song Swift has ever had, courtesy of the adult contemporary chart.

After all that, the waves of backlash Swift had received in 2016 and 2017 didn’t actually translate to career disarray. Instead, Swift doubled down on maximum commercialization; she partnered with ESPN to preview a single during a college football game, and partnered with UPS to plaster promotional posters on its brown trucks. If she was going to be a snake, she was going to be an ultracapitalist snake. Though her period of media silence took her out of the spotlight, Reputation sold over a million copies in its first week. And while the New York Post had initially reported that the Reputation tour was “shaping up to be a disaster” in 2018, it ended up as the highest-grossing U.S. tour ever, beating the Rolling Stones’ 70-date tour from 2005 to 2007 with only 38 dates.

Although Reputation was all about spurning haters, Swift did appear to take some of the criticism she received in 2016 to heart. During the 2018 midterm elections, she explicitly endorsed two Democratic candidates in Tennessee. “In the past I’ve been reluctant to publicly voice my political opinions, but due to several events in my life and in the world in the past two years, I feel very differently about that now,” she wrote in an Instagram post. “I always have and always will cast my vote based on which candidate will protect and fight for the human rights I believe we all deserve in this country.” She asked fans to vote; voter registration spiked. (The Republican incumbent senator who Swift spoke out against, Marsha Blackburn, won anyway.) After all the tumult, Swift’s belated decision to get political showed that she was ready to change up certain aspects of her celebrity when necessary—but her next era was, in many ways, a reaffirmation of who she already was: an industrialist steamroller.

In April 2019, the same week a mural of multicolored butterfly wings popped up in the Gulch, a trendy neighborhood in Nashville, Swift released a new single, the first track off her seventh studio album, Lover. “Me!” featuring Brendon Urie of Panic! at the Disco, served as a statement on many things: her steadfast devotion to bubblegum pop, her spelling skills, her approach to brand tie-ins, and even, perhaps, her slightly fading power as a pop star. The media blitz for the song was a slick big-business spectacle; Swift announced it during an appearance at the 2019 NFL draft, then performed it at the Billboard Music Awards. But the song hit no. 2 on the Billboard Hot 100—an accomplishment for most artists, but an outright flop for Swift. “Me!” was her first lead single to fail to hit no. 1 in nearly a decade, since 2010’s “Mine.” Ironically, the song Swift couldn’t dislodge from the top spot was a country tune: “Old Town Road” by Lil Nas X.

Her next crack at a top track came this summer, when she released the candyland-colored video for “You Need to Calm Down” in June, which is also Pride month. It features a parade of LGBTQ stars sipping tea and frolicking, including RuPaul, Ellen DeGeneres, and the lyric “shade never made anyone less gay.” “The lyrics seemed to be comparing homophobia to people being mean online,” Jones said.

“Its a breathtaking argument: that famous people are persecuted in a way meaningfully comparable to queer people,” Spencer Kornhaber wrote at The Atlantic, noting that the denoument of the song’s music video, in which Swift and Katy Perry appear to make amends, further confuses the message. “Thought this video was about gay rights? Nope, it’s primarily narrative management for superstars.” Then again, plenty of young gay fans adored the video, and it angered right-wing commentators—the clumsiness of her messaging aside, at least it was a choice to voice her beliefs. “Taylor, in this case, is in a position of she’s fucked if she does and she’s fucked if she doesn’t,” Elaine Lui said. “She is making a political statement. I believe it comes from a place of good. Was it executed perfectly? Probably not. However, the intention is there, and hopefully the execution can get better.”

Taylor Swift performs at this year’s iHeartRadio Wango Tango
FilmMagic for iHeartMedia

Pop predecessors like Madonna and contemporaries like Lady Gaga had explicitly aligned themselves with the gay community decades and years ahead of Swift, and had paid special attention to their LGBTQ audiences in a way that made their allyship seem more than just performative. Releasing “You Need to Calm Down” in 2019 marks Swift as behind. “It’s kind of something she should have done in 2014 or 2015,” Turner said. While Swift has identified her friendship with singer and dancer Todrick Hall as the impetus for this more overt move toward allyship, her tardiness makes it harder to enjoy the rainbow confection without parsing exactly how manufactured it was.

“I don’t think she fully grasped what people wanted from her,” Spanos said. “It’s not exactly what everyone was begging for.”

“A mass public shaming, with millions of people saying you are quote-unquote canceled, is a very isolating experience,” Swift told Vogue this summer, referring to her feud with the Kardashian-Wests and the public fallout from it. In the interview, Swift frames Lover as a return to positivity, a “love letter to love.” In the “Me!” video, a snake turns into butterflies; Swift is signaling a return to happiness, a move away from her spiky side. For all the hand-wringing, it’s not clear when, exactly, Swift was ever really canceled; she’s everywhere in the run-up to her album release, even on Pitchfork, which reviewed five of the singer’s previous albums in anticipation of Lover. (Red has a 9.0!)

While Lover is a step back into the sunshine after Swift’s shift into more confrontational music, she is still willing to publicly slug it out. This summer, Swift wrote an impassioned Tumblr post about facing her “worst-case scenario” after celebrity manager Scooter Braun bought the Big Machine Label Group, which controls her back catalog masters. She brought up her conflict with Kim and Kanye and accused Braun of being a bully, and Big Machine’s Scott Borchetta of betrayal. Things escalated from there: Bieber jumped on Instagram to defend Braun, other celebrities took sides, and Borchetta insisted Swift was lying—that she had not been blindsided by the sale, and had been given an opportunity to purchase her catalog. Although Swift’s narrative of the artist vs. the industry was a sympathetic one, the skeptical coverage of the brouhaha underlined how Swift’s swings at bigwigs don’t necessarily pack the same punch. In past years, people may have been more willing to see her as an unaware, innocent victim; in 2019, everyone is too familiar with the playbook. Instead, some of Swift’s best organic publicity this album cycle stemmed from Kid Rock aggro-tweeting about how she had succumbed to Hollywood liberalism, accidentally proving that her late-blooming political stance would help keep her in the news, after all.

Swift has come far from her Nashville roots by many metrics, but her fidelity to the concept of the traditional album rollout is putting her at odds with the newer generation of artists. Ariana Grande, for example, rejoiced when she abandoned the standard pop timeline and released Thank U, Next shortly after Sweetener just because she felt like it. Other rising stars, like Lil Nas X, never had access to this machinery; instead, he harnessed TikTok and meme culture to make “Old Town Road” this year’s summer anthem, and history’s longest-lasting no. 1 hit. Hip-hop is ascendant, Max Martin–era big industry pop is on a sharp decline, and adhering to a corporate machinery that appears increasingly unnecessary may hinder Swift in time. “Pop as a genre just doesn’t exist in the same way it did 10 years ago,” said critic David Turner. “The kids love Billie Eilish. I don’t really know what Taylor Swift does in a world where kids love Billie Eilish.”

“Taylor is also far too young to go the Pink or Kelly Clarkson route and age gracefully into brassy empowerment anthems that all sound like pleasant Ellen episodes unto themselves,” my coworker Rob Harvilla wrote earlier this summer, musing over how she could retain her former relevance. Taking the mom pop route—a perfectly fulfilling and well-compensated path, it must be said!—would be a premature change of course for Swift at this point, but it’s not a bad worst-case scenario. (And taking a role in the upcoming and spectacularly weird Cats movie, as Swift did, could be a good jump start down that road.) A better course change might be one that brings her full circle. “She could always just go back to country, and her career would be set,” Turner said.

One thing Taylor Swift does in a world where kids love Billie Eilish is that she partners with business behemoth Amazon to shellac Lover images on the company’s packages. Eilish might have the cool factor, but Swift is fiendishly corporate. One of her shrewdest strategies for juicing album sales figures is to “bundle,” which means offering the album as part of a deal selling merchandise like T-shirts and hoodies to fans. This isn’t a Swift-specific tactic; rapper Travis Scott recently used bundling and paired his concert tickets with his album in order to climb the charts. But it is yet another example of how much strategy goes into maintaining this level of success.

“I think that Taylor Swift is pretty indestructible,” Lui said. She’s right: Even if Lover underperforms, Swift is so ensconced in the industry that it’d take far more than one whiff to bring her down. “It’s her, Drake, and Beyoncé,” Spanos said. “If they released an album that critics totally hated it would not change anything for them.”

Swift is a long way from the up-and-coming country colt most famous for looking aghast at an awards show; she has built herself into an institution, which is why so many of her biggest stumbles have come when she has presented herself as the little guy in conflicts—the top dog can’t be the underdog, too. Taylor Swift may never eclipse the critical and commercial success of 1989, any future attempts to take political stands may be as ego-tripping as “You Need to Calm Down,” and I somehow doubt we’ve heard the last of her and Kanye’s feud, but if the past 10 years have taught us anything, it’s that her foibles don’t detract from her persona as much as they enhance its fascination. (Also, the single “Lover” is a return to form.) When the seams show as Swift tries to control the narrative, it is a reminder that her story and celebrity are now too large for any one person, no matter how shrewd, to steer. She’s not America’s sweetheart, but Swift has achieved an American Dream—she’s too big to fail.

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