20. Blake Shelton

With a mother who owned a beauty salon and a father who was a car salesman, becoming a successful country music singer wasn’t exactly in the cards for Blake Shelton. But after learning to play the guitar in his early teens, he began writing songs and traveling around the local bar circuit around his county. As soon as he graduated high school, he moved to Nashville in an instant. Going through the same path as a lot of people on this list, he started out in the business as a song-writer, before getting his own recording contract later. Beginning with a very traditional style, he had off and on hits throughout his early years. But a few things happened in the later 2000’s: he connected up with Miranda Lambert (soon after, they became an “it couple” in Nashville), he switched to adding more pop sounds to his songs, and he gained significant national attention by becoming a coach on the singing competition “The Voice”. These things all allowed him to continue getting hits and becoming one of the biggest names in the country genre. He is still in the midst of his radio career right now, and the longer that goes on the better shot he has of entering the Hall Of Fame in the future.