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Notorious for putting famous ex-boyfriends in her hit songs, Taylor Swift is a total pop meets country superstar. She began making music at the age of 11. By the time Taylor was 20, she had already won 4 Grammy awards and had 3 number one albums under her belt! Her hit songs “Love Story” and “You Belong With Me” were forever stuck in our heads during the summer of 2009, and the latter won her an MTV VMA for best female pop video. Her acceptance speech was famously interrupted by Kanye West, who insisted that Beyonce had the best female video with “Single Ladies.” That didn’t slow Taylor down though! Not only was she popular in music, but with the guys in Hollywood! Taylor has had flings with teen heartthrobs like Taylor Lautner, Joe Jonas, and the much older Jake Gyllenhaal and John Mayer. Taylor also became the youngest winner of the CMA’s entertainer of the year award!

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