Folklore, Evermore and Re-Recordings

In 2020, Swift released two surprise albums with little promotion, to critical acclaim. The first, her eighth studio album Folklore, was released on July 24. The second, her ninth studio album Evermore, was released on December 11. Swift wrote and recorded the albums while in isolation during the COVID-19 pandemic, working with producers Jack Antonoff and Aaron Dessner from the National. Both albums feature collaborations with Bon Iver, and Evermore features collaborations with the National and Haim.Swift's boyfriend Joe Alwyn co-wrote and co-produced select songs under the pseudonym William Bowery. The making of Folklore was discussed in the concert documentary Folklore: The Long Pond Studio Sessions, directed by Swift and released on November 25.

Both albums sold over one million units worldwide in its first week, with Folklore selling two million. Folklore broke the Guinness World Record for the highest first-day album streams by a female artist on Spotify, and was the best-selling album of 2020 in the U.S., having sold 1.2 million copies. Swift was 2020's highest-paid musician in the U.S., and highest-paid solo musician worldwide. At the 2020 American Music Awards, Swift won three awards, including Artist of the Year for a record third consecutive time. Folklore won Album of the Year at the 63rd Annual Grammy Awards, making Swift the first woman in history to win the award three times.

Following the masters controversy, Swift released the first re-recording of her back catalog, Fearless (Taylor's Version), on April 9, 2021. The re-recording of her 2008 album Fearless peaked atop the Billboard 200, becoming the first re-recorded album to do so, and was preceded by three of its tracks: "Love Story (Taylor's Version)", "You All Over Me" with Maren Morris, and "Mr. Perfectly Fine". "Love Story (Taylor's Version)", the re-recording of Swift's 2008 single "Love Story", made Swift the second artist after Dolly Parton to have both the original and the re-recording of a single at number one on the Hot Country Songs. Swift released "Wildest Dreams (Taylors Version)", the re-recording of her 2015 single "Wildest Dreams", on September 17, 2021, after the song gained traction on the online-video sharing app, TikTok. The second re-recording of her back catalog, Red (Taylor's Version)—the re-recording of her 2012 album Red—is scheduled for release on November 12, 2021.