Taylor Swift is undoubtedly one of the most famous musicians in the world. She was a superstar at age 20 and has won many Grammy Awards and even broken Guinness World Records. Her almost seamless transition from country music sweetheart to high-powered pop star gained her international attention and appeal, and eventually allowed her to flex her creative muscles at will. Throughout her career, Swift has stood for doing things her own unique way, whether that’s experimenting with new genres or re-releasing old music under her own creative control. Let’s look back at the most significant milestones of her dynamic career.
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1. 2008: Fearless
Swift’s first album, Taylor Swift, was released in 2006. While it was popular, the album pales in comparison to the success of her second album, Fearless. Fearless saw Swift taking her first steps toward pop music, and increasing her mainstream appeal. Released in 2008, it broke records as it spent 11 weeks at No. 1 on the Billboard charts and 35 weeks at the top of the country charts (placing just behind Shania Twain’s 1997 album Come on Over). While her first album had largely made waves in the United States, Fearless propelled her onto the international stage, topping charts in Australia, New Zealand, Canada, Norway, Japan, and the U.K.
2. 2010: First Grammy Award
Her first album garnered a Grammy nomination for Best New Artist. But in 2008, Fearless thrust her into the limelight and led to eight Grammy nominations. It won four: Best Country Album, Best Country Song, Best Female Country Vocal Performance (the latter two for the song “White Horse”), and the big one—the one that signaled the Swift of the 2010s would become the Swift of the 2020s— Album of the Year. Swift has garnered many more awards since then, but these first major accolades proved she belonged on the stage with the greatest musicians of her generation.
3. 2010: Start of film career
Swift made her feature film debut in the 2010 film Valentine’s Day, appearing opposite her then-boyfriend Taylor Lautner. She also performed “Today Was a Fairytale” on the film’s soundtrack. Since then, the singer has appeared in several feature films, including The Lorax, The Giver, Cats, and Amsterdam. Her acting career—underscored by several television appearances and countless award-winning music videos—has shown she’s a true superstar in every sense of the word. While Swift has always prioritized music over acting, she has said she is open to more acting roles in the future.
4. 2012: Transition to pop music
Starting in 2008, Swift’s albums stepped steadily away from country and toward pop music. Fearless was generally classified as pop country, while 2010’s Speak Now involved more of the former and less of the latter. But it wasn’t until her 2012 album, Red, that Swift fully embraced her new image as a pop star. The wildly popular album involved elements of rock, pop, electronica, and even dubstep. It marked a more mature sound for Swift, underscored by songs inspired by her relationships with several high-profile celebrities.
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5. 2021: Taylor’s versions
In 2021, Swift began re-releasing her past albums with the subtitle “Taylor’s Version.” This came after her split from her former producer, Scooter Braun, who, Swift claimed, had stifled her creative control for years. Between 2021 and 2023, Swift re-released six of her previous albums. These featured unreleased songs and verses as well as new music and lyrics for some songs. The new albums not only gave her the chance to control the direction of her own music—to great acclaim—but they also drew attention to the often-toxic conditions of a male-dominated music industry.
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