Over her illustrious 15-year career, for roughly one in three times that Taylor Swift is nominated for an award at a music awards program, it's safe to presume that she's going to win. Alongside seven CMT Music Awards, she's set a precedent for the most American Music Awards (32), Billboard Music Awards wins by a female artist (23), and most solo artist Teen Choice Awards wins (26) in history. For Swift, award wins per year tend to occur in impressive numbers. Thus, here, in order from most to least, are the years (and best-winning song) where Swift's sounds and talent reigned most supreme.
In 2015, Swift was named one of TIME Magazine's People of the Year. In regards to her success as a songwriter, Mariska Hargitay noted, "I’m always trying to find the best words to talk to my kids (and myself) about growing up, but you can’t top her beautifully articulated advice. The haters are gonna hate, but, well, shake it off. She illuminates our inner music that lets us dance to our own beat." Regarding her best-awarded song of the year, 2014-released -- and previously mentioned -- "Shake It Off" showed the expansion of her firm, country songwriting roots into the pop realm.
Taylor Swift received the Nashville Songwriters Association's Songwriter/Artist Award for the fifth and sixth consecutive years in 2012 and 2013. In regards to her 2013 honor, she told Billboard, “I think the goal for the next album is to continue to change, and never change in the same way twice. How do I write these figurative diary entries in ways that I’ve never written them before and to a sonic backdrop that I’ve never explored before? It’s my fifth album, which is crazy to think about, but I think what I’m noticing about it so far is it’s definitely taking a different turn than anything I’ve done before." Of those "diary songs," Red album single "We Are Never Ever Getting Back Together" was the best-seller.
2020 saw Swift release two critically-acclaimed surprise albums Folklore and Evermore, with the aid of producers Jack Antonoff and Aaron Dessner. Stylistically, they were a unique departure from five years of much more dramatically mainstream pop aimed material. Folklore won Album of the Year at the 63rd Annual Grammy Awards, making Swift the first woman in history to win the award three times. As for Evermore's lead single "Willow," the global platinum-seller and Billboard No. 1 single is described as a "chamber-folk ballad." Moreover, Swift won three awards at the American Music Awards in 2020, including Artist of the Year for a record third consecutive time.
2019 found Swift in a period of cautious discovery with her success and stardom in the digital age. Regarding her Reputation Stadium Tour, she noted the importance of retaining a human connection to herself and her career, to Entertainment Weekly by noting, when I go and I meet fans, I see that they actually see me as a flesh-and-blood human being. That—as contrived as it may sound—changed [me] completely, assigning humanity to my life." About this epiphany, her single "You Need To Calm Down" was a global top-five single and blended catchy pop songwriting and ambient vibes with a solid pro-LGBTQ message.
2011 was Taylor Swift's country-to-pop breakout year after a 2010 that saw her single "You Belong To Me" achieve peaking at number two on the Billboard Hot 100, plus being the first country song to reach number one on the all-genre Billboard Radio Songs chart. Moreover, the single was certified seven-times Platinum by the Recording Industry Association of America (RIAA), plus was named one of the greatest songs of the 2000s by CMT and VH1. In a feature for The New Yorker, she told the writer, Lizzie Widdicombe, that her "best musical experience" was "hearing a song by somebody singing about their life, and it resembles yours so much that it makes you feel comforted."