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.”
Grammy Darling

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.

Going Digital

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.

A New Era

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.

Another Surprise

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.

Return to the Grammys

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.

Going Back to the Beginning

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

The “Champagne Problems” singer was honored with the Global Icon Award at the BRIT Awards in May 2021. She is the first woman and first non-British star to be given the accolade in the show’s history. “I want to thank my friends and family who know exactly who they are,” Swift said during her speech, “whose opinion of me never changed whether my stock was up or down. If there’s one thing that I’ve learned, it’s that you have to look around every day and take note of the people who have always believed in you and never stop appreciating them for it.”

‘Red’ Revisited

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.

Meet Her at Midnight

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

Director Swift

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.”

Her ‘Eras’ Era

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.

Re-Enchanted

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

Box Office Boss

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.

The Year of Taylor

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.

All’s Fair in Love and Poetry

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.