Outlaw Country rose to prominence in the early 1970s, driven by many artists who are considered legends today. Legends have spawned from the vice-filled lives of early Outlaw Country performers. However, they weren’t abusing any more substances or sleeping with any more women than conventional country singers. The movement wasn’t about bringing criminality or drugs into country music. Instead, it was about creative freedom. More than anything, it was an answer to the strictly regimented and pop-leaning Nashville Sound.
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Waylon Jennings, one of the movement’s pioneers defined the term in his autobiography. “For us ‘outlaw’ meant standing up for your rights, your own way of doing things. It felt like a different music, and outlaw was as good a description as any.”
Some fifty years after the beginning of the Outlaw Country movement’s heyday, many of its pioneers have passed away. Today, we’re going to look back at the legends who helped change the face of country music forever.
Willie Nelson—One of the Last Living Outlaw Country Originators
Willie Nelson is one of the only Outlaw Country originators who is still alive and active. The only other high-profile Outlaw artists who are still around are David Allen Coe and Hank Williams Jr. However, they helped to popularize a movement that artists like Nelson, Tompall Glaser, Jerry Jeff Walker, and the other artists on this list helped to shape.
Nelson began his career as a songwriter in the ‘50s and moved to Nashville in 1960 in hopes of finding success. While he did find some success, it wasn’t enough to keep the lights on. However, he pressed on until 1970 when his ranch in Tennessee burned down. Seeing this as a sign, he moved back to Texas, cut ties with Nashville, and retired.
However, Nelson found a growing music scene among the hippies in Austin, Texas. More specifically, at the iconic Armadillo World Headquarters. This reinvigorated his desire to be a recording artist. He became the first country artist signed to Atlantic Records and, in 1973, he released Shotgun Willie, marking his first contribution to the Outlaw Country movement. At the same time, he convinced his friend and fellow Texan, Waylon Jennings to follow in his footsteps, something Jennings was already preparing for, whether he knew it or not.
Waylon Jennings—Remembered As an Outlaw Legend
Waylon Jennings is another artist who jumps immediately to mind when the term Outlaw Country is mentioned. He was more than a decade into a decently successful career when Nelson cut ties with Nashville and went back to Texas. Nelson’s popularity convinced RCA Records to renegotiate Jennings’ contract and gave him creative control. This led to the first two albums masterminded by the man himself—Lonesome On’ry and Mean and Honky Tonk Heroes.
These albums were the beginning of the most influential and commercially successful period in Jennings’ long career. Later, he would team up with his wife Jessi Colter, Nelson, and Tompall Glaser to record the compilation album Wanted! The Outlaws which would go on to be the first country album to obtain Platinum Certification from the RIAA.
A singer, songwriter, and inspiration to countless artists through the years, Jennings passed away on February 13, 2002, at the age of 64.
Billy Joe Shaver—A Largely Unsung Outlaw Country Hero
While Jennings had already started moving away from the Nashville Sound with Ladies Love Outlaws (1972) and Lonesome On’ry and Mean (1973), he truly codified the Outlaw Country sound with his 1973 album Honky Tonk Heroes. Billy Joe Shaver penned or co-penned nine of the ten tracks on that legendary album.
Unfortunately, Shaver never found favor with the mainstream crowd. However, other artists found success with his songs. Most notably, John Anderson had a hit with “I’m Just an Old Chunk of Coal But I’m Gonna be a Diamond Someday.”
Shaver may be the best example of Jennings’ definition of “Outlaw.” He lived life on his own terms, told his stories in his songs, and didn’t seem concerned with who liked them or didn’t at the end of the day. He passed away at the age of 81 on October 28, 2020.
Kris Kristofferson—A Hitmaking Songwriter and Outlaw Country Original
Kris Kristofferson is another largely unsung hero of the Outlaw Country movement. While he garnered more acclaim than Shaver, he didn’t see much more chart success. Instead, Kristofferson found more success as a songwriter. Artists including Nelson, Jennings, Ray Price, Johnny Cash, Elvis Presley, Janis Joplin, and many others had hits with his songs.
He was a member of the Highwaymen with his good friends Nelson, Jennings, and Johnny Cash and a member of the Country Music Hall of Fame. Outside of music, he found fame as an actor, starring in several films including A Star Is Born, Pat Garrett and Billy the Kid, Convoy, and the Blade trilogy.
Kristofferson was also a Rhodes Scholar at Oxford, a celebrated collegiate athlete, a U.S. Army Captain, and a helicopter pilot. Before he found success in Nashville, he worked for a petroleum company, flying helicopters in southern Louisiana. He wrote most of his early songs while sitting in a chopper’s cockpit. He also famously landed a helicopter on Johnny Cash’s lawn in hopes of hand-delivering some demo tapes.
He passed away at the age of 88 on September 28, 2024.
Johnny Paycheck—A Powerful Singer and Real-Life Outlaw
Most know Johnny Paycheck for songs like “Take This Job and Shove It” and “I’m the Only Hell (Mama Ever Raised).” However, like many of the originators of Outlaw Country, his history in the genre is deep. Born Donald Lytle, Paycheck went by a handful of names over the years. The most notable of his early incarnations was Donny Young.
Young was a member of George Jones’ band The Jones Boys in the ‘60s. He played bass and steel guitar and sang harmony alongside Jones. Additionally, he found early success as a songwriter, penning “Apartment No. 9” which was Tammy Wynette’s debut single.
He legally changed his name to Johnny Paycheck in 1964 and began finding success as a solo performer. Songs like “A-11,” “She’s All I Got,” and “Mr. Lovemaker” carried him through the mid-70s. Then, as Jennings and Nelson’s success rose under the banner of Outlaw Country, he changed his image and became part of the movement. He passed away on February 19, 2003.
“To me, an outlaw is a man that did things his own way, whether you liked him or not,” Paycheck said. “I did things my own way.”
Featured Image by Tim Mosenfelder/Getty Images
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