15. Taylor Swift

Does this one really need an introduction? Born in 1989, being named after James Taylor certainly began her on a music journey early in life. After watching a documentary about another artist on this list (Faith Hill), that inspired Taylor to pursue a career in country music. At 11, her and her mother travelled to Nashville. Not finding what she was looking for with that trip, she focused on her songwriting. Beginning work with regular Music Row songwriters, she eventually got a record label deal in 2005. Releasing her debut single in 2006, it was like her career was shot out of a rocket and hasn’t stopped since. She continued to get hits on country radio until 2013, when she herself made the decision to transition her music in a more pop direction. That essentially ended her time in the country music industry and stopped her country radio career, but she continued on to becoming the biggest superstar on the planet and still retains the respect of the Nashville community. She has basically won every accolade you can as an artist. There will be a very good chance she gets in the Hall of Fame down the line somewhere, but it’s a matter of does her switch to pop hold her back or does becoming the biggest artist in the world move her forward in odds?