18. Entertainer Of The Year
Taylor Swift opened the show with a winning performance at the November 2009 CMA awards. The 19-year-old singer had to wait until the end of the show to collect the biggest honor, entertainer of the year. There's no doubt that Taylor looked absolutely beautiful in this gold sequined gown, and she has definitely had a show stopping year. This is only the beginning for the young star, and there's no telling where her career and style will take us next.