Taylor Swift has undoubtedly had one of the biggest careers in music ever, one that continues to cross genres and break records time and time again. In October of this past year, Swift released her 12th studio album, The Life Of A Showgirl, which gave fans the flavorful pop persona they’ve come to expect and never question from the multi-Platinum artist. However, some fans will remember the time when a young Swift was a new face in country music. It feels like forever ago, but when you look back, it’s plain to see that she’s always been as iconic as she is now.
Videos by American Songwriter
Winning Her First Entertainer of the Year Award (2009)
In 2009, Taylor Swift was the star of the CMAs. The girl was up for four awards that night, including Album, Music Video, and Female Vocalist, and she swept all four. Not to mention, she also became the youngest person ever to win the Entertainer of the Year award and still is today. At a press conference backstage that night, Swift spoke about how awestruck she was. “Honestly, I never imagined that the unattainable thing that I’d always held in my mind happened to me at 19. And, I couldn’t be more grateful, but I love a challenge. And right now, the challenge is to find that next challenge.” Years later, it’s amazing to see how far she’s come!
The Highlight of Her Senior Year (2007)
When Taylor Swift first started to get noticed in country music, she gained popularity for songs like “Tim McGraw” and “Our Song”. It was also her self-titled album, which many fans refer to as “debut” that got Swift in with some of the major players and ultimately to the CMAs at just 17 years old. Alongside artists like Jason Aldean and Kellie Pickler, Swift was up for the Horizon Award, which the New Artist of the Year Award eventually replaced. “I can’t even believe that this is real,” a high school Swift said, close to tears on the CMA stage. “This is definitely the highlight of my senior year!”
The SNL Song-ologue (2009)
Although Swift has made many notable appearances on SNL since this one, I think her first is important to note simply because of all the moments she references in it from her early career. Swift sings her “Monologue Song (in parentheses, ‘La la la’)” and sings about all the things she’s not going to talk about. Some notable mentions are “Joe, who broke up with me on the phone,” and a certain “werewolf from Twilight” that Swift was dating at the time.
Photo by: ROBYN BECK/AFP via Getty Images











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