How Did Taylor Swift Become So Successful?

We chart the unbelievable career of the world’s biggest music artist, from her Nashville country music roots to her record-smashing Eras tour.

After the public and media beating Taylor Swift endured when rapper Kanye West and his then-wife, reality TV personality Kim Kardashian, levelled an attack on her character, Swift emerged from a year in hiding to release her sixth studio album, Reputation, in late 2017. Like everything the pop star releases, it was a commercial success, but the critics were mixed.

When Tree Paine, Swift’s publicist, told the singer she didn’t receive a Grammy nomination for the album, Swift was visibly devastated, with the moment filmed for Swift’s 2020 documentary film Miss Americana. She attempted to shake it off, resolving that her next album, Lover, would be better. But the snub stung and she began to wonder if her days as a global sensation were numbered.

Taylor Swift with fans
Taylor Swift attends the “Taylor Swift: The Eras Tour” Concert Movie World Premiere in Los Angeles, California. Credit: Getty.

“This is probably one of my last opportunities, as an artist, to grasp onto that kind of success,” she said wistfully to the camera in 2019. “As I’m reaching 30, I want to work really hard while society is still tolerating me being successful.”

That was four years and four Grammy-award nominated albums ago. As someone who felt her shelf life as a pop star was coming to an end, she could not have foreseen the level of success she is experiencing today. Right now we are watching history being made. Swift is on track to become the most successful musical artist of her generation – if not of
all time – during our lifetimes.

Taylor Swift Time magazine
Swift on the cover of Time magazine as their 2023 person of the year.

The story goes that Swift, famously born in 1989, grew up in Pennsylvania listening to singer- songwriter Shania Twain. When she was 14 her family – ever supportive – moved to Nashville so she could really compete in the country music capital.

She was signed by a record label at 15 and released her self-titled debut album at 16 – tapping into her massive fanbase on MySpace. Swift became the first female to write or co-write every song on a platinum debut country album in the US – an astounding feat at such a young age – but breaking records would become her forte.

A student of music and careers, Swift witnessed what had come before her and took notes. Record companies watched her first two country albums connect with the masses and sell millions. As they were hunting for the next Taylor Swift, the performer reinvented herself, shedding a musical skin before someone else could imitate it.

Taylor Swift and Mum
Swift and her mum Andrea Swift inn the audience at the 2010 American Music Awards.

In 2013 I witnessed the Swift inner sanctum – her personal tour bus (complete with gym) – during The Red Tour in Detroit. By then, Swift was already one of the most popular musicians on the planet, yet her mother, Andrea, would personally find fans in the back row or those with great outfits or signs and upgrade them to an area closer to the stage. Swift did a meet and greet with competition winners before the show, then spoke to local media.

After the performance, she’d walk off stage, freshen up, then head straight into a meet and greet. It was more than an hour of posing for photographs yet she still managed to make interaction genuine. “It’s the country music way,” Andrea said at the time. “We’ve been doing it since the very start.”

Team Taylor was always her parents, Andrea and Scott, and her brother, Austin. She’s often joked it’s a small family business – just now one that’s running a billion-dollar empire.

At that stage Swift was still doing interviews. She was fresh from dating fellow pop star Harry Styles, and a phalanx of publicists shut down those who didn’t honour requests to not ask about her personal life. Even back then, journalists missed the real story: the music.

Taylor Swift Jack Antanoff
Aaron Dessner, Taylor Swift and Jack Antonoff on the red carpet at the 63rd Annual Grammy Awards.

The star knew she didn’t need to name names, it was the emotion in her songs that people were drawn to, especially when they were going through the same feelings. She left clues in songs, videos and sleeve notes, leaving fans to decode them. Social media interaction saw Swifties become CSI-level DIY detectives.

“Break-ups are hard,” Swift told me. “And you need music to get through them. I am happy to be your go-to break-up musician. People like music when they’re in love but they don’t need it as much. You need music when you’re missing someone or you’re pining for someone or you’re forgetting someone or you’re trying to process what just happened. The heartbroken are a special kind of people. When you’re in that spot – when you’re going through it – I’ll be there to hold your hand.”

In 2013, CDs were being replaced by streaming. The music industry was changing, but Swift’s crystal-ball vision was impressive. She’d already started flirting with pop music in her 2012 album, Red. “I’m just happy I get to experiment [with different genres],” she told me in Detroit. “Most of my fans, if you were to look on their iPods, you’d see every possible genre of music represented in some capacity.”

Swift performing at the 2023 Eras tour. Image: Getty

By her fifth album, 1989, she had gone from merely flirting with pop to having breakfast with it the next morning. Swift managed to make thoroughly modern electronic music that retained her personal, intimate storytelling. And she started to clap back with a knowing wink: “Blank Space” pierced the tedious narrative that she was man-crazy, dating purely to get content for songs. In just over five years she’d totally transformed her music and become a superstar who transcended any genre.

But in that 2013 interview Swift said something that, in hindsight, is particularly interesting. On one track, ‘‘The Lucky One”, a composite based on several artists she’d never name, the lyrics detail an artist who became famous and had their “secrets splashed on the front page.” The star in the lyric took their “money and dignity and got the hell out”. Swift sings, “It took some time but I understand it now… I think you got it right.”

“I spend a lot of time looking at other people’s careers and watching them and taking note,” Swift told me. “When there’s a downfall – and you hate seeing downfalls – but when there is it usually comes from a loss of perspective [and] surrounding yourself with the wrong people. Downward spiralling into insecurity and self-obsession [is often] based on thinking everybody’s watching you all the time.”

Taylor Swift Kanye West
Kayne West jumps onstage as Taylor Swift accepts her award for the “Best Female Video” award during the 2009 MTV Video Music Awards.

Swift weathered the only real blip in her career with grace. After she disappeared for a year, 2017’s Reputation was her darkest effort, inspired by having been dragged into an off-brand war of words between rapper Kanye West and his then-wife, Kim Kardashian. “I would very much like to be excluded from this narrative,” Swift said politely at the time, coining a phrase that would enter pop culture just like her music. Any public backlash didn’t stop her becoming the first act to have four albums sell one million copies within a week in the US. The Reputation Tour went on to gross nearly $500 million.

But studying other people’s missteps didn’t prepare Swift for her former record label, Big Machine, in 2019 selling the lucrative master recordings of her first six albums to the highest bidder: one of her few enemies, pop manager Scooter Braun. The following year, Swift set about painstakingly rerecording one by one what fans refer to as the “stolen albums”, adding bonus, unheard tracks to entice fans to buy the same albums a second time.

Some artists have their sales dominated by physical formats such as vinyl, while others have a streaming fanbase. Swift has both. In this playlist and song-driven world, she has helped revive the album as a creative statement. She’s selling her albums on vinyl to young fans who didn’t know what vinyl is, boosting a trend many thought was the niche domain of music nerds. Swift even filmed one of her three-hour Eras concerts in the US and put it in cinemas in late 2023, funding the venture herself.

Taylor Swift NYU
Taylor Swift Delivers New York University 2022 Commencement Address at Yankee Stadium in 2022 in New York City.

When Time magazine named Taylor Swift Person of the Year in 2023, there was the usual subsection of threatened men who can’t deal with a female artist who has the power to boost the economy of any town she tours in. Proving there’s still work to be done, The Hard Men podcast host Eric Conn stated it was “shameful and sad that a hyper-promiscuous, childless woman, ageing and alone with a cat has become the heroine of a feminist age.”

Swift needs to waste neither the time nor the energy clapping back at the likes of Conn. Besides, she’s already written a song for such situations.

In “The Man” she sings, “I would be complex, I would be cool. They’d say I played the field before I found someone to commit to. And that would be OK for me to do. Every conquest I’d made would make me more of a boss to you.”

Taylor Swift
Swift performs live on stage in concert on the Sydney stop of her “Fearless” tour at The Factory Theatre in 2009 in Sydney, Australia.

Swift’s trajectory is stratospheric. Her impact stretches from TikTok videos to university courses based on her career and fandom. Her skill is to bring joy to millions, not to monetise fear. She has become a billionaire not through makeup or clothing like other musicians, but from her music. There are stadiums full of devoted fans who shout each of her words back at her.

Swift is a songwriter who will be judged with the greats. No other artist could release a 10-minute version of an album track nine years later (“All Too Well”) and have it go to No. 1 in the US (the longest song ever to do so). And it’s deservedly so. US Rolling Stone magazine contributing editor Rob Sheffield has ranked the 10-minute track as the best in Swift’s repertoire of 243 songs, writing that “her greatest song just got even greater in the definitive 10-minute version … “What kind of artist takes her own masterpiece and tears it all up? This one. Only this one. Result: an even bolder masterpiece.”

Taylor Swift
Swift with her longtime publicist Tree Paine in 2019.

What those outside the fanbase may miss is her precise attention to detail, her ability to write about an ultra-personal situation but make it universal, her vivid scene setting – pouring out her inner-monologue. And all this while managing to shoehorn in a killer bridge.

The indie-folk albums Folklore and Evermore, which Swift released during the pandemic, even won over the music snobs. And that’s the charm and the trick. The day-one fans are still there. And there are people who weren’t born when her first album was released but are now all onboard.

She’s opening doors for new artists to be authentic, and making sure they realise what they’re signing away in their contracts.

Her first Australian tour, in 2009, saw her play small, 900-person venues in Melbourne and Sydney. In February she’ll play seven stadium shows in those cities. Ticket demand means she could have added 10 more shows in each city and still not cater for everyone who wants to see her. Those figures, not even two decades into a career, show the sort of compelling grip on culture that instantly puts her up with Madonna, Coldplay, Paul McCartney and Michael Jackson.

The Eras Tour grossed more than $US1 billion in 2023, the first tour ever to do so. For an artist who has just turned 34, she is quite literally changing the entire game. As she sings in her song “Maroon”, from her 10th album, Midnights, “that’s a real fucking legacy to leave”.

Taylor Swift Red Tour
Swift took the European leg of her blockbuster The RED Tour show to Berlin’s, O2 World playing to a capacity crowd of more than 10,700 fans in 2014 in Berlin, Germany.

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