At the 2024 Grammys, Taylor Swift walked away as one of the biggest winners of the evening, which is nothing new for her. The singer claimed two new trophies, Album of the Year and Best Pop Vocal Album, for her latest release of original material, Midnights. When her name was called out, Swift became the first artist to take home the honor four times–beating three other superstars for this bit of history.
With a fourth Album of the Year Grammy now in her possession, Swift broke out of a tie with Frank Sinatra, Paul Simon, and Stevie Wonder, who all earned the honor three times in their careers. Just a few days after Swift won her latest Grammys, the family of one of the previous record holders has spoken out on social media about her win–and they’re thrilled for her.
“Congratulations @taylorswift on your Album of the Year win and breaking our dad’s record. You’re a champion for artists everywhere, and doing it your way,” said both Nancy and Tina Sinatra, two of Frank’s children. The siblings posted the sweet message on their dad’s Instagram alongside a black and white image of the legendary crooner. Frank also had a son, Frank Jr., who passed away in 2016.
Sinatra was the first musician to win Album of the Year three times at the Grammys. He earned his first of three of these specific trophies in 1960, at the second-ever ceremony, for his release Come Fly With Me! He doubled his total in 1966 with September of My Years. He then became the first artist to win a trio of Album of the Year honors the following year, with A Man and His Music.
Stevie Wonder was the second musician to earn three Album of the Year Grammys, and he managed the showing faster than anyone. He earned his trophies in 1974 with Innervisions, the next year with Fulfillingness’ First Finale, and two years later for Songs in the Key of Life.
Paul Simon is the only artist to collect three Album of the Years as both part of a group and a soloist. He and Art Garfunkel, as Simon & Garfunkel, won the top prize in 1971 with Bridge over Troubled Water. Half a decade later, he was back, that time as a soloist. His fourth solo collection Still Crazy After All These Years won the honor in 1976. Simon then returned for another moment on top in 1987 with Graceland.
Swift managed to snag four Album of the Year Grammys in a shorter span of time it took Simon, the most recent three-time winner, to collect his trio of trophies. She won what many consider to be the highest honor in music for the first time in 2010 with her sophomore set Fearless. She then added to her total with 1989 (2016), Folklore (2021), and Midnights (2024).
Of the four musicians mentioned, only Wonder has won every single time he’s been nominated for Album of the Year at the Grammys as an artist. Sinatra was nominated twice at the first Grammys in 1959, but he lost to Judy Garland. He also collected three more nods throughout his career. Simon was nominated a total of seven times, including his three wins. Swift has been up for the prize with six releases.
