21. Mary Chapin Carpenter

After being born in New Jersey and living in Japan for a couple years, her family settled in Washington D.C. and Mary had a regular suburban high school experience there. Although she enjoyed playing music, she never considered it as a career option. She would just play a couple gigs around her area and got a University degree in American Civilization. Once she got more involved in the Washington music scene, she met John Jennings (who would go on to be a friend and producer for her). Once John convinced her to play her original songs instead of covers, it would only be a couple years until she got a recording contract with Columbia. Her first album got some play on small college stations, but once Columbia advertised her as a country artist, that is when popularity came for her. She enjoyed a run of successful songs, in which she incorporated various sounds and unique lyrics. Once her radio career winded-down, she switched her musical style from radio-friendly tunes to a more calm and political direction. Her variety of work has gained her 5 Grammy awards and 17 Grammy nominations, as well as 2 ACM award wins and 2 CMA award wins.