The essence of outlaw country—hard living, broken hearts, and a life led rambling, among other things—is distilled in Waylon Jennings’ booming baritone. Born in Texas in 1937, Jennings dropped out of school at 16 with the dream of becoming a musician, and got his chance when rock ‘n’ roll pioneer Buddy Holly tapped him to play bass in his band. After giving up his seat for the infamous 1959 plane ride that would end the lives of Holly, The Big Bopper, and Ritchie Valens, Jennings established the honky-tonk roots of what would become his signature sound in the ‘60s with songs like the toe-tapping “Only Daddy That’ll Walk the Line.” But it wasn’t until the ‘70s that Jennings became the outlaw icon—a scruffy, towering cowboy in a wide-brimmed hat—of legend. Jennings made this version of himself known with 1973’s Honky Tonk Heroes, a record dense with electrifying twang and hardcore country that stood in stark contrast to the genre’s mainstream offerings in Nashville. While Music City might’ve had its issues with Jennings, he was in good company with songwriters, including fellow Texan Willie Nelson, a longtime collaborator he eventually joined in country supergroup Highwaymen—alongside Johnny Cash and Kris Kristofferson—in the ‘80s and ‘90s. Jennings passed away in the early 2000s, but his influence looms large over country music, particularly in its 2010s outlaw resurgence through artists like Sturgill Simpson and Chris Stapleton.