On November 24, 2019, Taylor Swift was named Artist of the Decade at the American Music Awards, held at the Microsoft Theater in Los Angeles and broadcast live on ABC. Swift was 29 at the time. The honor recognized a decade in which she released five studio albums and moved from country music to pop, a shift told in 1989.

Swift won six awards that night: Artist of the Decade, Artist of the Year, Favorite Female Pop/Rock Artist, Favorite Adult Contemporary Artist, Favorite Pop/Rock Album for Lover, and Favorite Music Video for "You Need to Calm Down." She arrived with 23 American Music Awards and left with 29, passing the record of 24 held by Michael Jackson for the most wins in the show's history.

She opened her segment with a medley of hits from across her career, and her parents sang along in the audience. The performance itself had become a public dispute weeks earlier. In a social media post on November 15, 2019, Swift said that Scott Borchetta and Scooter Braun, the owners of her early master recordings since June 2019, were putting her plans to perform her older songs at the ceremony in jeopardy, part of the conflict told in Battle of Masters. She did not mention them in her acceptance speeches, and she thanked her new label home, Universal Music Group and Republic Records.

The award arrived at a turning point. Lover, her seventh album and her first released through Republic, had come out in August 2019, and two months after the ceremony the documentary Miss Americana followed her through that period, told in Miss Americana. In the decade the award covered, she had won Album of the Year at the Grammys twice, for Fearless in 2010 and 1989 in 2016, and had released albums that sold more than a million copies in their first week, including Reputation, told in Reputation.

The record of 29 wins was a milestone in a career that began with her debut album in 2006, and she continued adding American Music Awards in the years that followed, during the Eras Tour era.