1. Merle Haggard
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Born during the Great Depression, Haggard scratched and clawed his way through the early years of his life. At a young age, he taught himself how to pay a guitar by listening to old records from Lefty Frizzell and Hank Williams. A teenage Haggard was in-and-out of juvenile detention halls and even spent some time in San Quentin Prison. By the 1960s, Haggard had cleaned up his act and began one of the most impressive careers for any musician. Over a 20 year span, Haggard released 38 No. 1 hits including songs like ‘Mama Tried,’ ‘Swinging Doors,’ and ‘Branded Man.’ Up until his death in 2016, Haggard was still producing top tracks. The Hag was enshrined in the Country Music Hall of Fame in 1994 and was awarded the Grammy Lifetime Achievement Award in 2006.