A Look at Taylor Swift’s Three Album of the Year Wins

Tony Madden

On Sunday evening, Taylor Swift joined the ranks of Frank Sinatra, Stevie Wonder and Paul Simon when she took home her third Grammy award for Album of the Year, this time for 2020’s “Folklore.”

Swift is the first woman to win the award three times: first for her breakout country album “Fearless” in 2010, and later for her first pure-pop album “1989” in 2016. We’re honoring history being made with a retrospective look at Swift’s three most highly revered records. 

Fearless (2008)

As early as 2006, Swift had already been making moves on country radio with tracks like “Our Song” and “Teardrops On My Guitar” from her self-titled debut album. Her breakout “Fearless” era came shortly thereafter in 2008, reconnecting country music to a younger generation.

Spending a total of 11 weeks at No. 1 on the Billboard 200 chart, “Fearless” became the longest ever chart topper by a female artist. Where Swift had already proven herself a force to be reckoned with in country music circles, she secured her relevance in pop music with crossover hits like “Love Story” and “You Belong With Me.” 

“Fearless” explores themes of young love, first heartbreaks and the fleeting days of youth with dreamy rock-infused country instrumentation. Swift’s wide-eyed optimism is evident in her youthful voice, which would mature on her records to come in the following decade. The maturity is evident on her 2021 release of “Love Story” dubbed “Taylor’s Version.”

As her mother, Andrea, wiped a tear from her eye in the Grammy Awards audience, Swift thanked the Recording Academy for such an accolade this early in her career.

“This is the story we’re going to be telling over and over again: in 2010 that we got to win Album of the Year at the Grammys,” she said in a shaky voice. “Thank you, thank you, thank you, thank you.”

1989 (2014)

By the time “Red” was released in 2012, Swift had begun experimenting in music that deviated from the traditional country lens of her first three records. Though her label at the time, Big Machine Records, was apprehensive, Swift made the ambitious jump from country to pure-pop stylings for 2014’s “1989.”

It was this era when Swift was launched into bona fide superstardom. With songs about the brashness of New York City and a love that never goes out of style – complete with bright synths and booming percussion that lacked on any of her previous work – Swift released a pop record like no other. 

1989 is a love letter to change, and all the beautiful things it can be. It’s an ode to honoring relationships for what they were, and not for how ugly they ended. As she sings in the album’s final track, 1989 is a reminder that we aren’t damaged for walking through so many of life’s rainstorms; they make us clean.

The 2016 Grammy Awards were a high point for Swift before an ugly feud with Kanye West after he claimed he was responsible for her fame and success in his song “Famous.” Swift made her feelings clear in her acceptance speech for her second Album of the Year win.

“As the first woman to win Album of the Year at the Grammys twice, I want to say to all the young women out there, there are going to be people along the way who will try to undercut your success or take credit for your accomplishments or your fame, but, if you just focus on the work and you don’t let those people sidetrack you, someday when you get where you’re going you’ll look around and you will know that it was you and the people who love you who put you there,” Swift said. “And that will be the greatest feeling in the world. Thank you for this moment.”

Folklore (2020)

In the height of pandemic blues, Swift made an unprecedented move in her career. Early in the morning on July 23, 2020, she announced the release of her eighth studio album “Folklore,” to be released that very evening. 

It was one of her most ambitious projects yet: a pop superstar releasing an album with an indie-folk aesthetic, complete with a Bon Iver feature and collaborations with Aaron Dessner of The National

“Before this year I probably would’ve overthought when to release this music at the ‘perfect’ time, but the times we’re living in keep reminding me that nothing is guaranteed,” Swift said on Twitter. “My gut is telling me that if you make something you love, you should just put it out into the world.” 

“Folklore” is the result of letting childlike whims run free in the mind. Storytelling is at the very core of this album, offering a compelling narrative structure woven in with a flourish of piano, acoustic guitar and the occasional banjo or harmonica. 

Swift tells stories of her own life, like how she noticed an “invisible string” of sorts that tied her to the love of her life. She also tells some made-up ones: the central characters of “cardigan,” “august,” and “betty” tell the tale of a teenage love triangle in a summer of heartbreak. 

“You guys met us in this imaginary world that we created, and we can’t tell you how honored we are forever,” she said on the Grammys stage. “Thank you so much and thank you to the Recording Academy. We will never forget you did this for us. Thank you so much.”