With an illustrious career that has spanned more than 15 years, Taylor Swift has been honored with a number of awards. That includes, of course, 11 Grammy Awards, including Album of the Year, which she’s won three times. In the upcoming 2023 ceremony, set for Feb. 5, Taylor is nominated for four more awards. Though her Red (Taylor’s Version) was not nominated for Album of the Year (a surprise to those who thought it would), she still has a chance to increase her growing collection of Grammy Awards. In fact, with more than 46 nominations in 15 years, Taylor has been highly recognized by the Recording Academy and has quite a history with the show.
In the future, Taylor may also get a chance to win Grammys for some of the SAME songs and albums that she’s already won for in the past. She’s currently in the process of re-recording her first six albums to own the rights to the songs, and the Recording Academy confirmed that she could win Grammys for the re-recorded versions — even if she’d already won an award (aside from songwriting awards) for those albums or songs in the past!
“Current eligibility guidelines would allow for the new performances and albums to be eligible if they were recorded within the last five years,” the Recording Academy told Billboard in 2021. “However, none of the older songs would be eligible for songwriting awards.”
So far, Taylor has released her re-recorded version of 2008’s Fearless and 2012’s Red. 2023 will see Taylor hit the road for the first time since 2018 with her Eras Tour. Whether or not Taylor releases more of her re-recorded music, she will likely be back for the 2024 ceremony on the strength of Midnights, the album she released in October 2022.
With all that said, here’s a look at Taylor’s history with the Grammys.
Although Taylor was nominated for her first Grammy Award (Best New Artist) in 2009, she didn’t take home her first trophy at the show until the 2010 Grammys, where she won four awards. Her wins included the most coveted award of the night, Album of the Year. Taylor, who was just 20 years old at the time, won for her second studio album, Fearless, which was released in the fall of 2008. She beat some of the biggest names in music — Beyonce, Lady Gaga, The Black Eyed Peas, and Dave Matthews Band — to take home the coveted honor.
“Oh wow, thank you so much,” Taylor said while accepting the trophy. “I just hope that you know how much this means to me and to my producer and all the musicians you see on this stage, that we get to take this back to Nashville. Our families are freaking out in their living rooms. My dad and my little brother are losing their mind in the living room right now. This is for my dad, thank you for all those times you said I could do whatever I wanted in life. And my mom, you’re my best friend. This is the story, all of us, when we’re 80 years old, and we’re telling the same story over and over again to our grandkids, and they’re so annoyed with us, this is the story we’re going to be telling over and over again. In 2010, how we got to win Album of the Year at the Grammys. Thank you!”
Fearless also won for Best Country Album in 2010, beating Zac Brown Band, George Strait, Keith Urban and Lee Ann Womack. At the time, Taylor was fully making country music, although she has since transitioned to become a full pop star. Taylor also accepted Best Country Album onstage at the Grammys, and was equally floored to have won such an incredible honor.
“This is my first time walking up those stairs to accept a Grammy on national television,” she gushed. “Thank you so much. I want to thank my record label for letting me write every song on my album. I just keep thinking back to when you’re in 2nd grade, and you sing at your talent show for your first time, and people joke around and say maybe we’ll see you at the Grammys someday, and that just seems like an impossible dream. I just feel like I’m standing here accepting an impossible dream right now, and I thank you so much for that.”
Taylor won Best Female Country Vocal Performance for her song “White Horse” in 2010, as well. This award was not given out during the main Grammys telecast, but Taylor got to accept the honor during a pre-televised portion of the event. She beat established country stars, Miranda Lambert, Martina McBride, Carrie Underwood and LeeAnn Womack, to win the award. This was officially the first Grammy award Taylor won.
“This is my first Grammy, you guys!” she said while accepting the honor. “I mean, this is a Grammy! I live in awe of the people I was nominated against in this category. I live in awe of my producer, Nathan Chapman, and all the wonderful, incredibly talented musicians in Nashville. Thank you to anyone who was a Grammy voter and decided it might be a good idea to vote for me for this. I’m so happy. Thank you so much!”
“White Horse” also won Best Country Song at the 2010 show. In that category, which was also announced in the pre-televised show, Taylor was up against Trace Adkins, Jamey Johnson, Lady Antebellum, and Billy Currington. She accepted the award with Liz Rose, who co-wrote the track with her.
“Liz Rose and I co-wrote this song together,” Taylor told the audience. “She started writing songs with me when she had absolutely no reason to do so. I didn’t have a record label, I didn’t have anything to offer her, but I’m so glad she wrote songs with me anyway.” Taylor then turned the microphone over to Liz, who added, “I have to thank Taylor. About six years ago, this curly-headed 14-year-old walked up to me and said, ‘Do you think you’d write with me sometime?’ Thankfully, I said yes.”
At the 2012 Grammys, Taylor received three nominations for her work on the 2010 album, Speak Now, and she won two of them. One was Best Country Solo Performance for her song “Mean,” which was one of the biggest country songs of the year. The other artists in the category were Jason Aldean, Martina McBride, Blake Shelton, and Carrie Underwood.
“Oh wow. This is fantastic,” Taylor said, while accepting the award at the show. “It’s always going to mean the world to me, the idea of getting to go to the Grammys and to possible have a chance at winning a Grammy. But this one means a lot to me. This one was for a song called “Mean” that I wrote. There’s no quite feeling like writing a song about someone who’s really mean to you and completely hates you and makes your life miserable, and then winning a Grammy for it. Thank you!”
It’s been reported that Taylor penned “Mean” as a response to a blogger named Bob Lefsetz, who criticized Taylor’s performance with Stevie Nicks at the Grammys in 2010. “I get that not everyone is going to like what you do,” Taylor has said about the song. “And I get that, no matter what, you’re going to be criticized for something. But I also get that there are different kinds of ways to criticize someone. There’s constructive criticism. There’s professional criticism. And then there’s just being mean. There’s a line that you cross when you just start to attack everything about a person, and there’s one guy who just crossed the line over and over again.”
“Mean” took home a second award, as well, when Taylor won for Best Country Song in 2012. In this category, she beat Blake Shelton, Thompson Square, Trace Adkins, Vince Gill, and Kenny Chesney, although the award goes to the songwriter. Taylor penned “Mean” completely by herself, along with the rest of the Speak Now album.
“Thank you to anyone who voted for this song, that is so incredible of you for doing that. Wow. This is another Grammy. I want to thank Scott Borchetta at Big Machine Records for letting me create this album and believing in this song and putting it out at radio,” Taylor said. “When we put this out as a single, a few people said, ‘Really? You’re going to do that?’ And my label stood by it, and country radio played it a lot, which was wonderful.”
Unfortunately, Taylor no longer has a close relationship with Scott, the head of her former record label. She left the label in 2018 when Big Machine would not allow her to buy the rights to the masters of her previous six albums. In 2019, Scott sold the masters to Scooter Braun for $300 million, which, Taylor says, she never had the opportunity to do. Rather, Scott wanted Taylor to record one new album to earn back the rights to each previous album. This is the reason that Taylor is now re-recording her music — so she can own the rights to the new versions herself!
At the 2013 Grammys, Taylor scored three nominations and won one award for Best Song Written for Visual Media. The award was for her collaboration with The Civil Wars on the track “Safe & Sound,” which was featured on the soundtrack for The Hunger Games. Taylor & The Civil Wars beat Arcade Fire, Birdy & Mumford & Sons, Katharine McPhee & Megan Hilty, and Jason Segel & Walter to win.
“This is unbelievable,” Taylor gushed. “I just want to thank my collaborators for working with me — the Civil Wars and T Bone Burnett, you guys are amazing. We just won a Grammy for that! I really want to thank Suzanne Collins for writing Hunger Games and Jennifer Lawrence, who was so fun to write from the perspective of. And I want my co-writers to go. Thank you, this is an honor!” Taylor then turned the microphone over to her co-writers to speak.
After Taylor’s 2012 album, Red, lost in the Album of the Year category at the 2014 Grammys, she vowed to write an even better and more cohesive album. Taylor produced 1989 in 2014, and it won big at the Grammy Awards in 2016. For 1989, she received her second Album of the Year award, beating out Alabama Shakes, Kendrick Lamar, Chris Stapleton, and The Weeknd.
The 2016 Grammys happened right around the time of Taylor’s re-ignited feud with Kanye West, stemming from his song “Famous.” Her Album of the Year speech included a direct dig at Kanye without using names. “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,” she said. “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 that put you there. And that will be the greatest feeling in the world. Thank you for this moment.”
In addition to Album of the Year, 1989 also won for Best Pop Vocal Album in 2016. In that category, Taylor beat Kelly Clarkson, Florence & The Machine, James Taylor, and Mark Ronson. The award was given out in the pre-televised portion of the show, and Taylor accepted via her phone since she was in rehearsals for her Grammys performance at the time. One of her producers and co-writers, Jack Antonoff, was there in person to do the honors.
Jack phoned Taylor, and she could be heard screaming, “We won!!!” as he relayed the news. She didn’t have a speech prepared but wanted to make sure everyone in the crowd knew how much she loved James Taylor. “If somebody sees James Taylor, tell him I love him!” she gushed. Jack concluded, “This was a massive album, but Taylor and I did a lot of this in a 600-square-foot apartment on an acoustic guitar, and it really means the world to be here. This is the coolest.”
Taylor’s music video for “Bad Blood” also won in 2016. The video premiered during the 2015 Billboard Music Awards, and featured some of Taylor’s famous friends. Some of the stars included Selena Gomez, Gigi Hadid, Cara Delevingne, Ellie Goulding, Hailee Steinfeld, Lily Aldridge, Ellen Pompeo, Mariska Hargitay and more. Selena was even by Taylor’s side during her big night at the Grammys!
This award was also given out during the pre-televised portion of the show, so Taylor once again wasn’t there in person to accept. However, she beat out A$AP Rocky, The Dead Weather, Kendrick Lamar (who was featured on “Bad Blood” and in the video), and Pharrell Williams.
In Taylor’s biggest Grammys night since the success of 2014’s 1989 album, she walked away with the highest honor of the evening — Best Album of the year for folklore. Joined by her collaborators Jack Antonoff, and Aaron Dessner, Taylor reveled in the incredible moment and drank in the major achievement of becoming the first woman in history to win Album of the Year 3 times and the 4th artist even in the history of the award show to do it at all. In her speech, she thanked her fans and her family, but she also thanked the first person she shared her new music with while she was writing: her boyfriend, Joe Alwyn.
As of Jan. 23, the Grammys haven’t announced the slate of performers. Taylor last performed at the 2021 ceremony, and the chances of her appearing at the Crypto.com Arena on Feb. 5 are a bit low. Roughly six weeks after the Grammys, she kicks off The Eras Tour, and preparation for that is underway. While this is the same Taylor who crashed a The 1975 concert to perform “Anti-Hero” live for the first time, it’s not beyond Taylor’s ability for her to play the 10-minute version of “All Too Well” at the Grammys (or any of the other songs off of Midnights).
If CBS wants to give Taylor the full time to do the extended version of the song, well — that remains to be seen.
As mentioned, after the Grammys, Taylor is going on tour. For those who were able to get tickets, fans will see Taylor on The Eras Tour as she plays music from throughout her career. Having been unable to tour for Lover, Folklore, and Evermore due to the COVID-19 pandemic, she’ll dip into those albums and 2022’s Midnights to delight fans across the United States. The tour kicks off in March and ends in August with a string of shows at Los Angeles’ SoFi Stadium. With International dates forthcoming, Taylor might spend 2023 on the road.
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