The Outlaw of Country Music
Waylon Jennings was one of the pioneers of the “outlaw country” movement in the 1970s. Born in 1937 in Littlefield, Texas, Jennings developed a love of music early on, learning to play guitar at age 8. He dropped out of high school to pursue a career in music, landing a spot as Buddy Holly’s bass player just before the singer’s tragic death in a 1959 plane crash.
Jennings moved to Phoenix in the 1960s and soon caught the attention of RCA Records. His early country hits like “Only Daddy That’ll Walk the Line” showcased his rough, rock-influenced sound. But Jennings chafed under the restrictive rules of the Nashville music industry. In the early 70s, he joined forces with Willie Nelson, Jessi Colter, and Tompall Glaser to create what became known as the “outlaw” subgenre of country.
Jennings’ outlaw albums like Honky Tonk Heroes and Dreaming My Dreams contained dark, introspective songs that helped redefine the country genre. Major hits from this era included “Luckenbach, Texas,” “I’ve Always Been Crazy,” and “Are You Sure Hank Done It This Way.” Jennings became known for his gritty baritone and rebellious persona.
Over his long career, Jennings released over 60 albums and earned platinum certifications for classics like Wanted! The Outlaws, Sweet Dream Woman, and Are You Ready for the Country. He won two Grammy awards and numerous Country Music Association awards, including Male Vocalist of the Year in 1975. Jennings was inducted into the Country Music Hall of Fame in 2001, just a year before his death.
Though his hard-living lifestyle took a toll on his health, Jennings’ musical legacy lives on. His outlaw country sound helped shape the genres of alt-country and americana. Artists from Hank Williams Jr. to Sheryl Crow have named Jennings as a major influence. Jennings’ “outlaw” attitude changed Nashville and country music forever.