4 Original Outlaw Country Legends Who Are Still Alive

In the ‘70s and early ‘80s, Billy Sherrill’s Nashville Sound dominated the country music world. Sometimes called “Countrypolitan,” it combined country instrumentation and vocals with background singers, string sections, and slick pop production. While the sound was incredibly popular it wasn’t for everyone. Those who bucked the system, fought for their creative rights, and made the kind of country music they wanted to make were branded Outlaws.

Many listeners have misconceptions about Outlaw Country. They may believe it’s drug-fueled country music or songs about doing illegal things. However, Waylon Jennings, a pioneer of the movement explained what it meant 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.”

Unfortunately, many of the original “outlaws” are gone. Billy Joe Shaver, Waylon, Tompall Glaser, Johnny Cash, and many more left this world after leaving their mark on it. Fortunately, some of the originals remain and are—for the most part—still making music.

Willie Nelson—An Outlaw Country Original

The lineage of Outlaw Country doesn’t go back much further than Willie Nelson. Many credit Waylon Jennings and his albums Ladies Love Outlaws and Honky Tonk Heroes with the codification of the subgenre. However, Nelson was one of the artists who gave him the push he needed to make the transition.

After years of being a clean-cut country singer. Nelson stepped into Outlaw territory when he released Shotgun Willie in 1973 and solidified his transition two years later with Red-Headed Stranger. As many country fans know, Nelson is still making music. His latest album The Border dropped in May 2024.

Jessi Colter—More than Waylon’s Wife

When the outlaw subgenre comes up in conversation, most people talk about the men who spearheaded the movement. After all, the subgenre is just as male-dominated as the wider country music sphere if not more so. However, not all outlaws were men. Jessi Colter, the wife of Waylon Jennings and mother of Shooter, was one of the few women in the movement.

“Waylon’s wife” is the easiest way to introduce Colter to the uninitiated. However, it still feels unfair. Her contributions to the music world go so much deeper than the man to whom she was married. Songs like “I’m Not Lisa” and “What’s Happened to Blue Eyes” are country classics. Additionally, she was heavily featured on the classic album Wanted: The Outlaws which showcased many forerunners of the movement. She also collaborated with Jennings on timeless tracks like “Storms Never Last,” “Wild Side of Life,” and “Suspicious Minds.”

Colter is still making music. She released her most recent album Edge of Forever in October 2023.

Kris Kristofferson—An Unsung Outlaw Country Hero

Many country music fans know Kris Kristofferson as an actor and one-fourth of the Highwaymen. However, his songwriting was an integral part of the Outlaw Country movement. To put things into perspective both Johnny Cash and Willie Nelson—skilled and prolific songsmiths—called Kristofferson one of their favorite songwriters. “Sunday Morning Comin’ Down,” “Help Me Make It Through the Night,” “Me and Bobby McGree, “For the Good Times,” and “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again” were among the many songs he penned.

For an example of Kristofferson’s Outlaw cred, spin his oft-overlooked 1972 album Border Lord.

Kristofferson is no longer performing or making music. He officially retired in January 2021. However, he’s still alive and well. So, there’s still a chance for new music from this criminally underrated outlaw original.

Steve Earle—An Outlaw Mentored by Legends

Many country music fans know Steve Earle for his 1988 hit song “Copperhead Road.” That song alone would give him all the Outlaw Country cred he would need to make this list. It’s rocking sound and subversive lyrics are about as outlaw as it gets. However, his resume is much deeper than that.

Earle was close friends with and mentored by two of the most lauded songwriters in country music history—Guy Clark and Townes Van Zandt. While he doesn’t copy either artist’s style, the lessons he learned from them are clear in the way the stories within his songs unfold.

Waylon Jennings gave the best possible definition of the Outlaw movement in his autobiography. Earle is the perfect example of an artist who does things their way. Over the years, the singer/songwriter has released albums in several styles from country rock to bluegrass and everything in between. Additionally, he has released albums of covers from Jerry Jeff Walker, Guy Clark, Townes Van Zandt, and his late son Justin Townes Earle.

Earle is still alive, well, and active. His latest album, Jerry Jeff, a tribute to his late friend Jerry Jeff Walker, dropped in May 2022.

Featured Image by Rick Diamond/Getty Images for Essential Broadcast Media