Toby Keith
An Oklahoma boy at heart, Toby Keith, entered the scene in 1993 with his hit single, Should’ve Been A Cowboy. This track landed at number one on the Billboard Hot Country Songs chart. Keith wasn’t happy to just be a singer, though, so he opened up a bar and girl in his home town of Oklahoma City. The bar was a smashing success and has since opened multiple locations. He is the wealthiest country star.
Josh Turner
Josh Turner is a country star that isn’t afraid to confess his faith and famously said that he doesn’t need to sing gospel to be a Christian musician. His debut album, Long Black Train, was launched following a successful deal signing with MCA Nashville Records back in 2003. It was actually his second album that contained two number one hits, Your Man and Would You Go With Me. His latest album was released in 2017.