Waylon Jennings Photography

After picking up the guitar at age eight and kicking off his performance career at 12, it was only a matter of time before Texan Waylon Jennings became a star. One of his earliest jobs was playing bass for Buddy Holly, and as fate would have it, Jennings gave up his seat on the fatal 1959 plane ride that became “The Day the Music Died.”

Jennings spent much of the 1960s fronting various bands and recording traditional country solo projects, but he truly blossomed in the ’70s as a forerunner in the “Outlaw Country” movement. Some of Jennings’ most enduring hits include “Luckenbach, Texas (Back to the Basics of Love)” “Mammas, Don’t Let Your Babies Grow Up to Be Cowboys” (both with Willie Nelson), and “Good Ol’ Boys” (best known as The Dukes of Hazzard theme).

From 1985 through 1995, Jennings found further fame alongside Willie Nelson, Johnny Cash, and Kris Kristofferson as a member of country’s most decorated supergroup—the Highwaymen. In 2001, Jennings was inducted into the Country Music Hall of Fame, but passed away just a year later from diabetes-related complications.