Johnny Cash, Waylon Jennings, Willie Nelson, and more come to mind as we list our favorite heavy hitters of the outlaw country genre.
Outlaw country isn’t as much a specific sound as it is a mindset. It’s the belief that no one — not your label, management, fans or foes — defines who you are other than yourself.
An outlaw does what they want when they want and how they want. The following musicians model this ethos to a “T”, painting a picture of the movement and how it has evolved since gaining popularity in the 1970s.
Between “Folsom Prison Blues” and his other prison concerts, the album Bitter Tears: Ballads of the American Indian and his long standing support of Indigenous tribes, and his countless hits including “A Boy Named Sue” and “I Walk The Line”, there’s no doubt that “The Man In Black” was an outlaw through and through.
Photography: Don Hunstein/Sony Music
David Allan Coe
An originator of the movement and as uncompromising an outlaw as any, David Allan Coe is best known for songs like “You Never Even Called Me By My Name,” “If That Ain’t Country,” and “Willie, Waylon And Me”. Signature throughout all of these songs were the artist’s rugged baritone and intermingling of country, blues, and rock that delivered a hard driving, no-holds-barred sound that led to his success throughout the 70’s and 80’s.
Often referred to as the First Lady of Outlaw Country, Jessi Colter is best known for her chart-topping hit “I’m Not Lisa” and collaborations with husband Waylon Jennings like “What’s Happened To Blue Eyes.” Her legacy continues to live on with the release of Edge Of Forever — her first album since 2017’s The Psalms — in October of this year as well as through modern day outlaws like Nikki Lane and Margo Price, the latter of whom produced her latest project.
Best known for his No. 1 hit “The Devil Went Down To Georgia,” Charlie Daniels was one of country and southern rock’s most respected artists for over a half century. The “Drinkin’ My Baby Goodbye” singer also held an Elvis Presley songwriting credit (“It Hurts Me”) and played on studio recordings for Bob Dylan’s Nashville Skyline, Ringo Starr’s Beaucoups of Blues, and Leonard Cohen’s Songs of Love and Hate, further cementing his outlaw and cross-genre status.
Photography: Erick Amderson
Bursting onto the scene in the 80’s with hits like “Guitar Town,” “Copperhead Road,” and “The Devil’s Right Hand,” Steve Earle has become a mainstay in the modern day outlaw movement through his songs, political views, collaborations with artists like the Del McCoury Band and son Justin Townes Earle, novels and other creative endeavors.
A Depression-era youth who was incarcerated several times growing up, Merle Haggard eventually cleaned up his act, going on to produce 38 No. 1 hits from 1960 to 1980 like “Working Man Blues,” “Think I’ll Just Stay Here And Drink,” and “The Bottle Let Me Down” that championed blue collar work and more.
From rowdy days shredding with Drive By Truckers (“Goddamn Lonely Love”) to his poetic, socially conscious present as bandleader of The 400 Unit, Jason Isbell’s bluntness (“White Man’s World”) and relentless introspection (“Cover Me Up”) make him one of today’s most celebrated — yet, still somehow underrated — songwriters. If his thought-provoking songs and online trolling wasn’t enough, he also appears in Martin Scorsese’s latest film Killers Of The Flower Moon.
A Highwaymen and pioneer of the outlaw movement, Waylon Jennings’ songs like “I’ve Always Been Crazy,” “Luckenbach, Texas,” and “Waymore’s Blues” remain country music staples to this day. The artist is also largely responsible for launching the outlaw movement with 1976’s Wanted! The Outlaws, a compilation album featuring Willie Nelson, Jessi Colter, and Tompall Glaser that went on to become country music's first platinum album.
Frequently referred to as the “greatest living country singer” prior to his death in 2013, George Jones is known just as much for hits like “He Stopped Loving Her Today,”“Golden Ring,” and “Tender Years” as he is for his battle with substance abuse, which infamously culminated in him riding a lawnmower to town to get his liquor fix in the late 60’s. The artist is also revered for his collaborations with one-time wife Tammy Wynette depicted on Showtime’s biographical drama George & Tammy.
A true songwriter with penned songs like “Me and Bobby McGee,” “For the Good Times,” “Sunday Mornin’ Comin’ Down,” and “Help Me Make It Through the Night,” all finding success with other artists. Kris Kristofferson was thrust into the mainstream with his starring role in the film A Star Is Born in 1976 and later as a member of the Highwaymen in the 80’s.
Everyone’s favorite “Coal Miner’s Daughter,” Loretta Lynn made it out of Butcher Hollow, Kentucky, to become one of the most successful, beloved, and influential country music artists of all time. A sweet southern belle, Lynn was also never afraid to speak her mind on everything from abortion (“The Pill”) to women who pursued her husband while she was touring (“Fist City”) to the stigma of divorce (“Rated X”) and more.
Willie Nelson isn’t just one of the most recognizable artists in country music, he’s one of the most recognizable artists in all of music. Songs like “On The Road Again,” “Seven Spanish Angels,” “Mamas Don’t Let Your Babies Grow Up To Be Cowboys,” and countless others have gone on to become part of the fabric of American music and culture. Even at 90 years old, Nelson continues to perform to gigantic crowds of gleeful listeners excited to catch a glimpse of the living legend doing what he does best.
Although David Allan Coe’s “Take This Job And Shove It” was arguably his biggest hit, Johnny Paycheck went on to have some certified twangers of his own like “Mr. Lovemaker” and “Me And The IRS”. Over the years, Paycheck had several run-ins with the law, further adding to his polarizing persona and demeanor.
From songs like “Hurtin’ (On The Bottle)” and “Twinkle Twinkle” to her outspoken stances on everything from weed to abortion, Margo Price is a an expert at making waves, turning heads, and keeping people guessing as to what she’ll do next.
The first Black performer on the Grand Ole Opry since founding member DeFord Bailey, Charley Pride’s rise in the 60’s and 70’s came with great strife. The “Snakes Crawl at Night,” “Kiss an Angel Good Mornin,’” and “Mississippi Cotton Picking Delta Town” singer battled with racism and depression throughout his career while also collecting 30 No. 1 hits and cementing himself at the center of the country universe.
Billy Joe Shaver
Countless past and present outlaws trace their musical lineage back to Billy Joe Shaver, making him one of the most influential outlaws on this list. Following the “Live Forever,” “Wacko From Waco,” and “Georgia On A Fast Train” writer’s death in 2020, artists like Willie Nelson, Miranda Lambert, George Strait, Allison Russell, Margo Price, Rodney Crowell, and Steve Earle came together to honor his legacy with Live Forever: A Tribute To Billy Joe Shaver, which highlights his biggest hits while also casting them in a new light.
His Merle Haggard and Buck Owens-infused vocals, paired with a genre-defying sound that he refused to “Keep It Between The Lines,” make Sturgill Simpson outlaw to the bone. The Kentucky born artist is as versatile as they come with Grammy nominations across four genres — Americana, country, rock and bluegrass — in the past decade alone as he continues to make top notch music with no barriers.
One of the few women in the early days of the outlaw country movement, Sammi Smith first found success in 1970 with a cover of Kris Kristofferson’s “Help Me Make It Through The Night” followed by more charting success with originals like “I’ve Got To Have You,” “The Rainbow in Daddy's Eyes,” and “Long Black Veil” later in the 70’s.
Townes Van Zandt
You’d be hard-pressed to find an outlaw country show that doesn’t include a cover of “Pancho and Lefty,” “For the Sake of the Song,” or “If I Needed You,” all three of which you can thank Townes Van Zandt for. The native Texan and adopted Tennessean was the epitome of an outlaw, regularly playing dive bars, staying in cheap motels, and battling with drug and alcohol addiction throughout his illustrious career prior to his death in 1997.
Country music wouldn’t be the same if Hank Williams wasn’t around to help lay its foundation. One of the most influential artists of the 20th century, Williams’ songs like “Your Cheatin' Heart,” “Hey, Good Lookin,’” and “I’m So Lonesome I Could Cry” were among his 55 Top 10 hits that all came in the span of 15 years prior to his tragic and unexpected death on New Years Day 1953 in the back seat of a car traveling to a show in Canton, Ohio.