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The country singer is mostly known for his musical mix of pop, country and Christian which came from his background as a church choir singer in his youth. His single, “I’m So Lonesome I Could Cry” which was a cover of the hit Hank Williams song gained over a million sales and launched Thomas’ career. He has won several Grammy Awards and was recently inducted into the Grammy Hall of Fame for his iconic song, “Raindrops Keep Fallin’ on My Head”, which was featured in many films and video-games.
Jo Dee Messina
Net Worth: $9 million
Venture: Bigger Than This
Two-time Grammy award nominee Jo Dee Messina is a perfect example of a country singer taking the music industry in a perfect sequence of events. From a young age, Dee Messina was proving herself to be a very talented musician. She would tour her state of Massachusetts with her brother and play music in various local clubs. She was discovered eventually and signed a label deal with Curb in the early ‘90s. Her career skyrocketed from there and resulted in her releasing six hit singles in a short time span.