Why 2019 Was the Year Taylor Swift Couldn't Stop Winning

Three years removed from a time she's dubbed "the apocalypse", Taylor Swift has thoroughly shaken off the haters. The non-stop awards and recognition? Those are just a bonus.

By Sarah Grossbart Jan 31, 2020 2:30 PMTags
Watch: Necessary Realness: Loving Taylor Swift

As she stared down at yet another Artist of the Year trophy, Taylor Swift took a moment to get real about the preceding 12 months. 

"The last year of my life has had some of the most amazing times and also some of the hardest things I've gone through in my life," the pop star shared with the American Music Award audience last November. "This year for me has been a lot. It's been a lot of good, a lot of really complicated." 

The complicated is somewhat easy to deduce: There's the whole Scooter Braun and Scott Borchetta debacle involving her old label still owning her collection of masters—the original recordings of her first six multi-platinum albums that she recently shared she "would have paid so much for" had she been able to purchase them.

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And there's her mother Andrea Swift's ongoing battle with first breast and now brain cancer. "While she was going through treatment, they found a brain tumor," she revealed in an emotional interview with Variety earlier this month. "And the symptoms of what a person goes through when they have a brain tumor is nothing like what we've ever been through with her cancer before. So it's just been a really hard time for us as a family."

It's a situation that inspired her to skip her standard studio tour for 2020's Lover Fest, a handful of dates that afford her a bit of wiggle room in her normally jam-packed schedule. "This is a year where I have to be there for my family—there's a lot of question marks throughout the next year," she told Billboard last year, "so I wanted to make sure that I could go home."

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As for the good, well, there was a lot of it in 2019.  

The Pennsylvania native who spent her tweens door-knocking ever studio on Nashville's music row earned another six American Music Awards at the November event, bringing her total to 26, a number that topples the record Michael Jackson has held since 2009. Fittingly, she was named the show's first ever artist of the decade and she received a similar honor the day before her 30th birthday at Billboard's Women in Music, the magazine touting her as their woman of the decade.  

She also put out an album she's calling her "new beginning"—her seventh studio disc, Lover, of course, debuting at number one, with all 18 tracks simultaneously charting on the Billboard Hot 100, and going on to become the year's top-selling album within two days of its August released. (It garnered her three Grammy nods as well.)

Plus she was named one of TIME magazine's annual 100 Most Influential People, Forbes' highest paid celebrity of 2019, thanks in large part to her hugely successful reputation tour, and the year's most influential person on Twitter

Taylor Swift's 2019 American Music Awards Easter Eggs

And then there's the fact that she's in the healthiest and happiest relationship of her adult life. Her forever with boyfriend of two-plus years Joe Alwyn all but assumed, it's a relationship she credits with getting her through some of the darkest moments of her career.

Having kept much of their love story shrouded in mystery, she peeled back the curtain just a little in her newly released Netflix documentary, Taylor Swift: Miss Americana, including footage of their previously unseen, sweet moments together.

In fact there's quite a bit she got off her chest in the film, from the constant scrutiny of her appearance that led her to develop disordered eating habits to just how hard she worked to be a people pleaser, concealing her real feelings lest someone happen to not agree with them. 

Now, though, whether it's her liberal slant on politics or how she felt taking the stand to detail being groped by a radio DJ, she's done keeping it to herself. "I feel really good about not feeling muzzled anymore and it was my own doing," she said in the film. "There's nothing that feels better than this moment."

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And it all started with following her own advice. Or rather, discovering the lessons the hard way, then advocating that others skip that part and just take her word for it. 

Because Swift has been through it the past few years. Long before her stand-off with Braun and Borchetta was making headlines, there was that dust-up with Kim Kardashian and Kanye West. The backlash was, um, swift and plentiful. Suddenly everything the musician did—from dating Tom Hiddleston to ending things with Tom Hiddleston to not publicly announcing her preferred candidate in the 2016 election—was just wrong

"If I did something good, it was for the wrong reasons. If I did something brave, I didn't do it correctly. If I stood up for myself, I was throwing a tantrum," she shared with Rolling Stone this fall. "And so I found myself in this endless mockery echo chamber.

During the worst of it, she continued, "You feel like you're being completely pulled into a riptide. So what are you going to do? Splash a lot? Or hold your breath and hope you somehow resurface? And that's what I did." 

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Specifically, she took a little me time, "recalibrating" her life, as she put it to Billboard "to make it feel more manageable." That meant pulling back on the level to which she let fans in a bit, choosing to keep the new romance she was diving into with British actor Alwyn completely private ("I've learned that if I do [talk about it], people think it's up for discussion, and our relationship isn't up for discussion," she explained to UK's The Guardian last August) and reassessing her approach to social media. 

"Because there were some years there where I felt like I didn't quite know what exactly to give people and what to hold back, what to share and what to protect. I think a lot of people go through that, especially in the last decade," she explained to Billboard. "I broke through pre-social media, and then there was this phase where social media felt fun and casual and quirky and safe. And then it got to the point where everyone has to evaluate their relationship with social media. So I decided that the best thing I have to offer people is my music."

So she turned off the comments on Instagram as a nod to her own self-care. "I think it's healthy for your self-esteem to need less internet praise to appease it, especially when three comments down you could unwittingly see someone telling you that you look like a weasel that got hit by a truck and stitched back together by a drunk taxidermist," she wrote in Elle. "An actual comment I received once." 

And she cleansed her life of anyone bringing the drama: "You only have so much room in your life and so much energy to give to those in it. Be discerning," she advised. "If someone in your life is hurting you, draining you, or causing you pain in a way that feels unresolvable, blocking their number isn't cruel. It's just a simple setting on your phone that will eliminate drama if you so choose to use it."

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By not just shaking off, but truly blocking out the haters, she was able to truly reclaim her voice. 

For the first time ever, she made her political and social positions known, steeling herself against those that didn't agree with her supporting Tennessee Democrat Phil Bredesen. And when she released her second Lover single, "You Need to Calm Down", it was an unabashed celebration of the LGBTQIA community, complete with a call for fans to sign her Change.org petition in support of the Equality Act. 

The track, she has since shared, was inspired by a conversation she had with friend and choreographer Todrick Hall in which he asked what she would do if her son were gay. "The fact that he had to ask me…shocked me and made me realize that I had not made my position clear enough or loud enough," she told Vogue. "If my son was gay, he'd be gay. I don't understand the question." But if it had occurred to him, she shared, "I can't imagine what my fans in the LGBTQ community might be thinking. It was kind of devastating to realize that I hadn't been publicly clear about that."


So she was, serving up an impossibly catchy anthem and a video filled with cameos by everyone from Queer Eye's Fab Five to Billy Porter to Ellen DeGeneres to pal-turned-frenemy-turned friend once more Katy Perry, their on-camera hug serving as the physical embodiment of their squashed feud.

"When you advocate for something, it has to be completely disconnected from what people say about you advocating for it. It should be removed from hard numbers," she told People, though it's worth noting her political musings caused a spike in voter registration and her petition is steadily climbing to 600,000 signatures. 

She's not done speaking out either, her next cause championing for artists' rights, having already gotten her new label to agree to pay musicians a "significant portion" of the money they pocket from Spotify shares. "If I'm in a position to speak about it—which thankfully I am—and somebody who's younger who's signing a record deal can learn from that, then that's a good day," she told People

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Not to mention it's been liberating to be completely transparent about where she stands. "I think when your public opinions on things are known, it makes me feel like my fans are able to know me more. It feels like what I believe in and what people know I believe in are aligned," she continued. "That is a really great sense of relief to have as a person who for 15 years has been trying to navigate what is public and what isn't. It's a nice moment right now to know I can say what I believe in, and I can disconnect from if people don't like that."

The rest of the disc is quite simply a celebration of everything else that's happening in her world. reputation and the ensuing tour affording her the chance to get everything off her chest, she wrapped the 53 dates feeling "in the healthiest, most balanced place I've ever been," she told Rolling Stone. "After that tour, bad stuff can happen to me, but it doesn't level me anymore." 

Dave Hogan

And she was able to put together Lover, the first disc in a long while, she shared with People, that wasn't a reaction to how people saw her: "In the past, I've definitely used my criticism as a jumping-off point for creativity. With reputation, I'd said everything I needed to say. I'd been tried in every possible way people could throw things at me, and I felt like now I just get to create."

Having already solidified that her brand of music doesn't require her to be lovelorn or scorned—"There's a common misconception that artists have to be miserable in order to make good art, that art and suffering go hand in hand. I'm really grateful to have learned this isn't true," she told Elle—she was able to put out tracks that were a true celebration of the romance that has come in her life, a process she likened in The Guardian to feeling like "I could take a full deep breath again." 

The lyrics of "London Boy" and "Afterglow" are the closest we're going to get to commentary on their romance, but suffice to say Swift is the happiest she's ever been, wiling away a solid chunk of her time in Alwyn's British hometown at local pubs or visiting his family. While it's incredibly unlikely we'll ever hear her say it, she's currently living out her love story—all that's left is to say yes to his inevitable proposal. 

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And now, having shaken off the haters and reclaimed her narrative, she's ready for her next decade. "I've been told by a lot of people [your 30s] are really fun," she told People, "and I'm having a really good time approaching them."

Year one seems awfully promising between the announcement that she'll be honored with the Vanguard Award at April's GLAAD Media Awards, this summer's Lover Fest and the planned re-recording of her masters beginning in November. "It's going to be fun, because it'll feel like regaining a freedom and taking back what's mine," she mused to Billboard. "When I created [these songs], I didn't know what they would grow up to be. Going back in and knowing that it meant something to people is actually a really beautiful way to celebrate what the fans have done for my music."

As for whatever else comes next, we're fairly certain Swift is ready for it. 

(Originally published Dec. 12, 2019, at 12 p.m. PT)