In the late 2000s , teenager Taylor Swift became the first country artist to enjoy widespread mainstream popularity since the 1980s , when artists including Ronnie Milsap , Dolly Parton , Eddie Rabbitt and Kenny Rogers regularly recorded music that appealed to both country and pop audiences . Two of Swift 's songs – " Love Story " and " You Belong With Me " – both reached the top 5 of the '' Billboard '' Hot 100 ( and No. 1 on several of the Hot 100s component charts ) after topping the Hot Country Songs chart . At the 2009 MTV Video Music Awards , Swift became the first country artist to win a VMA award when she won in the Female Best Video category for " You Belong With Me "
2009 MTV Video Music Awards
2009 MTV Video Music Awards
2000s in music