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Taylor Swift Through the Years: From Nashville Upstart to Pop Superstar

Taylor Swift started writing songs about love and breakups in the early 2000s, but her talent was soon recognized by music executives who knew she was the real deal. From releasing her first record in 2006 to gracing stages all over the world this star has earned her place in the Hollywood A-list music scene.

“I remember people asking me, ‘What are you gonna write about if you ever get happy?’” Swift recalled to Elle magazine in March 2019. “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. Finding happiness and inspiration at the same time has been really cool.”

In April 2021, Swift officially began a new journey, rereleasing her old albums, beginning with Fearless (Taylor’s Version) after a very public feud with Scooter Braun and former Big Machine Records owner Scott Borchetta over the rights to her first six albums.

“Artists should own their own work for so many reasons,” Swift wrote via Instagram in March 2021 about the process. “But the most screamingly obvious one is that the artist is the only one who really knows that body of work.”

Scroll down to revisit Swift’s epic journey to stardom:

Swift emerged in the music scene in June 2006 with her first lead single, “Tim McGraw,” named after, but not inspired by, the iconic country crooner. The track marked her first of many Top 40 hits on Billboard’s Hot 100 list.

The curly-cued country singer released her first album later in 2006. The self-titled record featured many songs Swifties still know and love today, including “Teardrops on My Guitar,” “Our Song,” “Picture to Burn” and “Should’ve Said No.”

The Nashville native continued to grow her following in November 2008 after dropping her second album, Fearless, which later became the top-selling album of 2009. She also joined Keith Urban’s Escape Together world tour that year

Swift earned her first Grammy in 2009. She went home with eight nominations that year and won four awards.

The critically acclaimed singer faced a troublesome moment in 2009 after her song “You Belong With Me” won an MTV Video Music Award for Best Female Video. While accepting the accolade, Swift was interrupted by Kanye West, who told her that Beyoncé deserved to win. However, the “Single Ladies” songstress later graced the stage and praised Swift for her work.

Swift swept fans off their feet in October 2010 with her emotional third album, Speak Now, which fans believed chronicled her relationships with John Mayer, Taylor Lautner and Joe Jonas, as well as alluding to her tense interaction with West.

Not slowing down! In October 2012, Swift released Red. The record showcased her transition from country music to pop, with catchy tracks like “I Knew You Were Trouble” and “We Are Never Ever Getting Back Together.” It also highlighted her ill-fated relationships with Connor Kennedy and Jake Gyllenhaal.

Swift bid her blonde curls farewell in 2013 and opted for stylish waves in 2013 while touring Red.

In October 2014, Swift released 1989, her first true pop album. The upbeat record featured fewer ballads, which Swift was known for her in early career, and instead, introduced groovy tunes.

Swift hit the road again with a fresh new look in 2015 and toured 1989. The album was widely believed to include subtle nods to ex Harry Styles.

While attending the Met Gala in 2016, Swift met British actor Alwyn. They started dating later that year and have been going strong ever since. She has kept her romance with him under wraps, but referenced their love in future songs.

Swift launched an unforgettable world tour in 2018, traveling to many different countries to perform Reputation.

Forget everything you know about Swift. In October 2017, the songstress took the world by storm and released Reputation, her pop album with references to Joe Alwyn, ex-boyfriend Calvin Harris as well as her successful career and the price of fame.

The Grammy winner announced on her 29th birthday that her Reputation concert special will air on Netflix on New Year’s Eve 2018. “You made this tour so insanely fun for all of us on stage, and I’m really excited that we will have this memento of the memories we all made together this year,” she wrote on Instagram.

Swift released “Me!,” the first single from her seventh album, in April 2019 after weeks of Instagram teasers. The track and its colorful music video feature Brendon Urie from Panic! at the Disco. “‘Me!’ is a song about embracing your individuality and really celebrating it and owning it,” Swift said in a pre-release interview with Robin Roberts during the 2019 NFL Draft.

The Pennsylvania native left her burn book behind her with Lover, her seventh studio album, released in August 2019. Us Weekly deemed the album “whimsical” and “triumphant,” with “a little something for everyone.”

In a wide-ranging October 2019 Rolling Stone cover story, Swift expounded upon her feuds with Kanye West and music manager Braun, her reconciliation with Katy Perry, her songwriting process and her views on success. “The times when I felt like I was going insane was when I was trying to maintain my career in the same way that I ascended,” she told the mag. “It’s easier to get power than to keep it. It’s easier to get acclaim than to keep it. It’s easier to get attention than to keep it.”

The “Lover” singer accepted the Artist of the Decade honor at the American Music Awards in November 2019 and performed a medley of her greatest hits after accusing Braun and Big Machine Records CEO Borchetta of blocking her from performing any of her old material during the live show. (The men have denied the claims.) During her acceptance speech, she thanked her dedicated fans: “The last year of my life has had some of the most amazing times and also some of just the hardest things I’ve gone through in my life. … I wanted to thank you so much for being the thing that has been a constant in my life.”

Swift accepted the Billboard Woman of the Decade Award in December 2019 and again referenced her drama with Braun and Borchetta before crediting her peers for having her back. “The most amazing thing was to discover that it would be the women in our industry who would have my back and show me the most vocal support at one of the most difficult times,” she said.

The artist gave fans an inside look at her life and career with her Miss Americana documentary in January 2020. “When I started filming, it was before she’d come out politically,” director Lana Wilson told Variety that month. “She knew that she was coming out of a very dark period, and wanted to collaborate on something that captured what she was going through and that was really raw and honest and emotionally intimate.” The Netflix film features Swift’s unfiltered thoughts on politics, her musical success, love with Joe Alwyn and more.

While isolating amid the coronavirus pandemic in July 2020, Swift announced the release of her eighth studio album, Folklore. “Most of the things I had planned this summer didn’t end up happening, but there is something I hadn’t planned on that DID happen,” she tweeted at the time. “I wrote and recorded this music in isolation but got to collaborate with some musical heroes of mine.”

In November 2020, the Recording Academy announced that the “Betty” singer was up for six Grammys, including Album of the Year for Folklore, ahead of the 63rd annual ceremony.

Since Swift could not do a Folklore tour due to the pandemic, she teamed up with coproducers Jack Antonoff and Aaron Dessner to perform all 17 tracks at the National member’s upstate New York studio for a Disney+ special, Folklore: The Long Pond Studio Sessions, which premiered in November 2020.

The Cats actress began rerecording her first five albums in November 2020 once her contract with Big Machine Records officially ended. After she teased the new version of “Love Story” in a Match commercial, fans noticed that the lyrics changed from “Baby, just say, ‘Yes’” to “Baby, just said, ‘Yes,’” sparking rumors that she and Alwyn had secretly gotten engaged.

Less than five months after releasing Folklore, Swift dropped a companion album titled Evermore in December 2020. “I’ve never done this before. In the past I’ve always treated albums as one-off eras and moved onto planning the next one after an album was released,” she wrote via Instagram at the time.

The musician got back on the Grammys stage for the first time in five years in March 2021. She performed a medley of songs from her album Folklore, including “Cardigan,” “August” and “Willow,” from a woodsy set. Swift also took home her 11th Grammy with her Album of the Year win for the same record.

The “Love Story” singer released her first rerecorded album, Fearless (Taylor’s Version), in April 2021. The record featured six new tracks from Swift’s vault, including “Mr. Perfectly Fine,” which some fans think is about either ex-boyfriend Joe Jonas or Jake Gyllenhaal.

Making History on a Global Level

Swift (and ex Jake Gyllenhaal) made headlines in November 2021 when she released Red (Taylor’s Version) and included the 10-minute version of “All Too Well,” a track long-rumored to be about the actor. Red (Taylor’s Version) was the most-streamed album in a single day from a female artist in Spotify history.

Swift’s 10th studio album, Midnights, dropped.

Days before her 33rd birthday, news broke that Swift is set to direct her first feature film for Searchlight Pictures.

“I always wanted to tell stories,” she said in an episode of Variety’s Actors on Actors with playwright Martin McDonagh. “I have always written stories, poetry, songs. And I think this just grew out of that storytelling. And the more I did it, the more I loved it.”

Swift returned for her first tour in five years in March 2023. She kicked off her Eras Tour with a 44-song setlist at State Farm Stadium in Glendale, Arizona.

Swift re-released Speak Now in July 2023, the same month she started seeing NFL player Travis Kelce.

In October 2023, Swift released Taylor Swift: The Eras Tour concert movie via AMC Theaters and earned about $250 million at the worldwide box office. Weeks later, she dropped 1989 (Taylor’s Version), which sold 1.6 million copies in the first week of release. It was her biggest first week for an album yet, per Billboard.

That same month, Bloomberg reported that Swift had officially reached billionaire status thanks to The Eras Tour.

Swift ended 2023 on a high note by being named TIME’s Person of the Year. Sporting a black turtleneck bodysuit and black sheer tights, she graced the magazine’s December 2023 cover with her cat Benjamin sitting on her shoulders.

Swift released her 11th studio album, The Tortured Poets Department, which featured several songs rumored to be about her past romances with Joe Alwyn and Matty Healy and her relationship with Travis Kelce. The album broke several records upon its April 2024 release, including becoming the first album in Spotify history to reach 300 million streams in a single day.


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