Waylon Jennings had a long career on the country music charts and he's a member of the Country Music Hall of Fame, but he made his name as a Nashville outsider. A radio DJ and guitarist since his teens, he moved to Lubbock, Texas and joined Buddy Holly
's band in 1958. (Jennings was schedule to go on the plane that crashed and killed Holly in 1959, but gave up his seat to J.P. "The Big Bopper" Richardson.) Jennings formed his own band in 1963, and Chet Atkins
brought him to RCA in 1965 to become a mainstream country artist. He had a hit and won a Grammy for his version of "MacArthur Park" (1969), but his career really took off in the 1970s, after he developed a more rock-influenced, stripped down sound and cast himself as an "outlaw" of the Nashville music scene. Doing things his own way, he had success on the pop and country charts in the late 1970s, thanks in part to his 1976 album Wanted: The Outlaws
, a collaboration with Willie Nelson
, Tompall Glaser and Jennings's wife, Jessie Colter. By 1980 Jennings had five platinum LPs and a string of hits including "Luckenbach, Texas," "Amanda" and the Nelson duets "Good Hearted Woman" and "Mammas Don't Let Your Babies Grow Up to Be Cowboys." He went on to work with Nelson, Kris Kristofferson and Johnny Cash
as The Highwaymen, and in the '90s he performed at rock venues and worked with the likes of Sting
and Sheryl Crow
. He died of diabetes-related complications in 2002.