American singer-songwriter Taylor Swift has received many awards and nominations throughout her career. Swift signed a record deal with Big Machine Records in 2005 and released her self-titled debut studio album in 2006, which was nominated for an Academy of Country Music Award. At the 50th Annual Grammy Awards, 18-year-old Taylor earned herself a Best New Artist nomination, but lost to Amy Winehouse. Her second studio album, "Fearless" (2008), spawned five singles, including "Love Story", "White Horse", and the MTV Video Music Award for Best Female Video-winning "You Belong with Me". Swift was subsequently nominated for eight categories at the 52nd Annual Grammy Awards and won four of them, including Album of the Year. At only 20, Taylor became the youngest artist to win in the category, having held the record for eleven years, till 2020. "Fearless" became the first album to win the American Country Award, Country Music Association, Academy of Country Music Award, and Grammy Award for Album of the Year, making it recognized as the most awarded album in history of country music.