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Taylor Swift’s Best Surprised Faces

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Still in shock! With more than one hundred award nominations throughout her impressive career, you’d think Taylor Swift wouldn’t be all that surprised to receive another trophy.

The country-turned-pop star won her first Grammy Award in 2009, scoring the prestigious Album of the Year win for her second studio record, Fearless. The wins kept coming that night as she took home Best Female Country Vocal Performance, Best Country Song and Best Country Album. As she climbed onstage to accept the honors, Swift clasped her hand over her mouth in utter disbelief.

As her winning streaks continued over the years, the Pennsylvania native’s candid expressions that accompanied each major award she received became notorious, meme-worthy moments. For her second Album of the Year win at the 2016 Grammys, Swift made a powerful statement about unabashedly celebrating her accomplishments in the face of criticism.

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,” the “Look What You Made Me Do” singer said at the time. “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. And that will be the greatest feeling in the world.”

In March 2021, Swift became the first woman to have three Album of the Year wins, winning the Grammy for her eighth studio album, Folklore. Not only has the Miss Americana star made Grammys History, but she’s also earned 23 Billboard Music Awards, 12 Country Music Association Awards, eight Academy of Country Music Awards and a Brit Award.

The Cats actress also holds the record for most American Music Award wins by any musician with 32 trophies. While accepting the Artist of the Decade award at the 2019 AMAs, Swift shared the special moment with the fans who’ve stayed by her side through it all.

“The fact that this is an award that celebrates a decade of hard work and of art and of fun and memories, all that matters to me is the memories that I have had with you guys, with you the fans, over the years,” she said at the time. “Guys, we’ve had fun, incredible, exhilarating, extraordinary times together, and may it continue. Thank you for being the reason why I am on this stage, from the very first day of my career until tonight.”

Scroll down to see all of Swift’s most outrageous surprised faces through the years!

June 16, 2009
The curly-haired country cutie seemed genuinely stunned by her win at the 2009 CMT Music Awards in Nashville, Tenn., where she took home the Video of the Year trophy for her fairytale-themed “Love Story.”

 

September 13, 2009
Swift wasn’t the only one surprised by Kanye West’s sudden appearance onstage at Radio City Music Hall. In a now-infamous moment at the 2009 MTV Video Music Awards, the rapper interrupted the young star’s acceptance speech for “Best Female Video” to argue that the award should have gone to Beyonce’s “Single Ladies” clip. (The “Red” singer later wrote about the incident in the song “Innocent.”)

November 11, 2009
The “Fearless” singer’s surprise was well-earned at the 43rd Annual Country Music Association Awards, where she became, at 19, the youngest artist ever to be nominated for, and win, the Entertainer of the Year honor.

January 31, 2010
At the 52nd Grammy Awards pre-telecast, the then-20-year-old took home two trophies, for Best Female Country Performance and Country Song of the Year. “This is my first Grammy, you guys!” she exclaimed in disbelief.

January 31, 2010
Swift’s surprised face made several appearances at the 52nd Grammy Awards, where she took home four trophies and became the youngest artist ever to win the coveted Grammy for Album of the Year. “People make so much fun of me for that [face],” she told Nightline later. “I don’t know. It’s like, if you win an award, isn’t that crazy? How do you sit there and be like ‘Oh, another Grammy. I guess I’m gonna get that now.'”

April 18, 2010
Fresh off her performance of “Change” at the 2010 ACM Awards in Las Vegas, the singer was surprised backstage by a group of friends and admirers.

January 5, 2011
The singer — in a pale peach J. Mendel frock — started her year off right with a win for Favorite Country Artist at the People’s Choice Awards in L.A.

April 3, 2011
The country superstar was anything but mellow in yellow when she won Entertainer of the Year at the 46th Annual ACM Awards in Las Vegas. (She was also nominated for the honor in 2010 but lost out to two-time winner Carrie Underwood.)

January 5, 2011
The singer — in a pale peach J. Mendel frock — started her year off right with a win for Favorite Country Artist at the People’s Choice Awards in L.A.

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