Outlaw country music has never followed the rules. It is raw, real, and filled with rebellion. The artists who shaped this genre stood apart, defining their careers with grit, independence, and a refusal to conform. From the smoky honky-tonks of Texas to sold-out arenas, these musicians lived by their own code, creating a sound that resonated with those who craved authenticity.
Prepare to explore the heart of a movement that defied the norms, stood tall against the grain, and changed country music forever.
Biggest Outlaw Country Stars
- Johnny Cash
- David Allan Coe
- Jessi Colter
- Charlie Daniels
- Steve Earle
- Merle Haggard
- Jason Isbell
- Waylon Jennings
- George Jones
- Kris Kristofferson
- Loretta Lynn
- Willie Nelson
- Johnny Paycheck
- Margo Price
- Charley Pride
- Billy Joe Shaver
- Sturgill Simpson
- Sammi Smith
- Townes Van Zandt
- Hank Williams
1. Johnny Cash
| Best Songs | “Folsom Prison Blues,” “I Walk the Line,” “A Boy Named Sue,” “Ring of Fire” |
| Notable Albums | *At Folsom Prison*, *Bitter Tears: Ballads of the American Indian*, *American Recordings* |
| Awards | Grammy Lifetime Achievement Award, Kennedy Center Honors, Country Music Hall of Fame |
| Key Themes | Rebellion, Justice, Redemption, Hardship |
| Legacy | Defined the outlaw spirit in country music, advocacy for prison reform and Indigenous rights |
Johnny Cash did not just sing about life’s struggles. He lived them. With his deep voice and dark clothes, he stood as a symbol of defiance. He sang for those who felt trapped by the system and the pain of their circumstances.
His prison concerts showed this. They connected him to an audience that understood suffering. Cash never pretended to be perfect. That was his power. He let the rough edges show.
His music was not clean or polished. It carried a rawness that resonated with people who wanted truth, not perfection. “Folsom Prison Blues” and “I Walk the Line” told real stories, not fantasies. He became a voice for the unheard.
Also, check out the best country singers known for their deep voice.
2. David Allan Coe
| Best Songs | “You Never Even Called Me by My Name,” “If That Ain’t Country,” “Willie, Waylon and Me” |
| Notable Albums | *Penitentiary Blues*, *Longhaired Redneck*, *Rides Again* |
| Awards | No major awards, but regarded as a major influence in outlaw country |
| Key Themes | Freedom, Rebellion, Hard Life, Pride |
| Legacy | Uncompromising sound blending country, blues, and rock, known for his independent attitude |
David Allan Coe lived his music in the same way he wrote it—on his own terms. He did not care about fitting into anyone’s mold. With a voice full of grit and stories about hard living, he became an originator of outlaw country.
His songs often cut deep, reflecting the life he lived in and out of prison. Coe never toned things down for the sake of acceptance.
His mix of country, blues, and rock broke barriers. He wasn’t interested in anyone’s approval. His music spoke for itself, loud and raw. Songs like “If That Ain’t Country” made a clear statement. Coe stood outside the lines, and that’s exactly where he wanted to be.
3. Jessi Colter
| Best Songs | “I’m Not Lisa,” “What’s Happened to Blue Eyes,” “Storms Never Last” |
| Notable Albums | *I’m Jessi Colter*, *Mirriam*, *Edge of Forever* |
| Awards | No major awards, but hailed as a pioneering woman in outlaw country |
| Key Themes | Love, Independence, Loss, Resilience |
| Legacy | Known as the First Lady of Outlaw Country, continues to inspire modern artists |
Jessi Colter’s voice stood out in a genre dominated by men. She wasn’t just part of the outlaw country movement, she shaped it. Her chart-topping hit “I’m Not Lisa” reached listeners beyond the genre, showing her wide appeal.
Colter stayed true to her style, never losing her unique blend of vulnerability and strength. Her influence runs deep in country music, and her legacy continues through the next generation of female artists.
Here you can read more about the Best Country Artists of the 90s.
4. Charlie Daniels
| Best Songs | “The Devil Went Down to Georgia,” “Long Haired Country Boy,” “Drinkin’ My Baby Goodbye” |
| Notable Albums | *Fire on the Mountain*, *Million Mile Reflections*, *Simple Man* |
| Awards | Grammy Award for “The Devil Went Down to Georgia” |
| Key Themes | Southern Pride, Rebellion, Humor, Good vs. Evil |
| Legacy | Pioneered blending country with southern rock, known for his high-energy performances |
Charlie Daniels brought a fiery edge to outlaw country with his blend of southern rock and traditional country. “The Devil Went Down to Georgia” became a defining song for both him and the genre. Daniels was known for his powerful performances and his ability to mix humor and intensity.
He spent over 50 years delivering music that spoke to southern roots, rebellion, and deep pride.
5. Steve Earle
| Best Songs | “Guitar Town,” “Copperhead Road,” “The Devil’s Right Hand” |
| Notable Albums | *Guitar Town*, *Copperhead Road*, *Train A Comin’* |
| Awards | Multiple Grammy Awards |
| Key Themes | Politics, Rebellion, Hardship, Freedom |
| Legacy | Strong political voice in country, pioneer of modern outlaw sound |
Steve Earle brought political sharpness and raw storytelling to outlaw country. His breakout hit “Guitar Town” in the 80s launched a career full of songs that went deeper than most. Earle wasn’t afraid to tackle tough topics, whether in “Copperhead Road” or later works.
His music combined grit, rebelliousness, and a drive for truth. He remains a force in the modern outlaw country scene, inspiring countless artists with his unapologetic approach.
6. Merle Haggard
| Best Songs | “Mama Tried,” “Okie from Muskogee,” “The Bottle Let Me Down,” “Working Man Blues” |
| Notable Albums | *Sing Me Back Home*, *If We Make It Through December*, *Back to the Barrooms* |
| Awards | Country Music Hall of Fame, Grammy Lifetime Achievement Award |
| Key Themes | Blue Collar Life, Redemption, Patriotism, Struggle |
| Legacy | Defined the working-class voice in country music, pioneer of the Bakersfield sound |
Merle Haggard’s voice captured the spirit of the working man. His rough upbringing and time spent in prison gave his music an authenticity few could match. Songs like “Mama Tried” and “Okie from Muskogee” struck a chord with everyday people.
Haggard’s blend of personal hardship and social commentary made him an iconic figure in both country music and American culture.
7. Jason Isbell
| Best Songs | “Cover Me Up,” “If We Were Vampires,” “Something More Than Free” |
| Notable Albums | *Southeastern*, *The Nashville Sound*, *Something More Than Free* |
| Awards | Multiple Grammy Awards |
| Key Themes | Introspection, Recovery, Social Commentary, Love |
| Legacy | Modern voice of outlaw country, blending personal and political in his lyrics |
Jason Isbell’s music brings a thoughtful and emotional depth to modern outlaw country. His songs explore personal struggles, social issues, and the complexities of love and recovery.
Isbell’s transition from rowdy band member in Drive-By Truckers to introspective solo artist has made him one of the most respected voices in contemporary country music.
8. Waylon Jennings
| Best Songs | “Luckenbach, Texas,” “Are You Sure Hank Done It This Way,” “I’ve Always Been Crazy” |
| Notable Albums | *Honky Tonk Heroes*, *Dreaming My Dreams*, *Are You Ready for the Country* |
| Awards | Country Music Hall of Fame, Grammy Award |
| Key Themes | Rebellion, Independence, Outlaw Life, Freedom |
| Legacy | Father of outlaw country, his music inspired generations of independent artists |
Waylon Jennings became the face of outlaw country. His refusal to conform to Nashville’s expectations set him apart. With songs like “Luckenbach, Texas,” Jennings stood for independence.
He worked alongside other legends to create an entirely new sound. Jennings was instrumental in the rise of the outlaw movement, and his influence continues today.
9. George Jones
| Best Songs | “He Stopped Loving Her Today,” “The Grand Tour,” “Golden Ring” |
| Notable Albums | *I Am What I Am*, *Bartender’s Blues*, *The Battle* |
| Awards | Country Music Hall of Fame, Grammy Lifetime Achievement Award |
| Key Themes | Love, Heartbreak, Struggle, Redemption |
| Legacy | Known as one of the greatest voices in country music, revered for emotional delivery |
George Jones was often called the greatest voice in country music. His heartfelt delivery made songs like “He Stopped Loving Her Today” legendary. Jones lived a turbulent life, and it showed in his music.
His battles with addiction and heartbreak became central themes. Despite personal struggles, his voice and emotional depth made him an icon.
10. Kris Kristofferson
| Best Songs | “Me and Bobby McGee,” “Sunday Mornin’ Comin’ Down,” “Help Me Make It Through the Night” |
| Notable Albums | *Kristofferson*, *The Silver Tongued Devil and I*, *Jesus Was a Capricorn* |
| Awards | Country Music Hall of Fame, Golden Globe Award |
| Key Themes | Love, Despair, Freedom, Social Issues |
| Legacy | Influential songwriter and key figure in both outlaw country and American music |
Kris Kristofferson brought a poetic depth to outlaw country. He wasn’t just a singer, he was a storyteller. His lyrics captured the pain, freedom, and complexity of life. Songs like “Me and Bobby McGee” became anthems, not just for country, but for American music.
Kristofferson’s career went beyond music as he also found success in acting. His artistry continues to influence both songwriters and performers.
11. Loretta Lynn
| Best Songs | “Coal Miner’s Daughter,” “Fist City,” “The Pill,” “You Ain’t Woman Enough (To Take My Man)” |
| Notable Albums | *Coal Miner’s Daughter*, *Don’t Come Home A-Drinkin’ (With Lovin’ on Your Mind)*, *Van Lear Rose* |
| Awards | Country Music Hall of Fame, Grammy Lifetime Achievement Award, Kennedy Center Honors |
| Key Themes | Women’s Rights, Struggles, Love, Independence |
| Legacy | Pioneered female independence in country music, outspoken about social issues |
Loretta Lynn’s voice resonated with women everywhere. Her songs were honest reflections of a life filled with struggle and resilience. She wasn’t afraid to tackle taboo subjects, making her one of the most daring figures in country music.
“Coal Miner’s Daughter” told her personal story, while songs like “The Pill” challenged societal norms. Lynn’s fierce independence and determination helped pave the way for future generations of female artists in country music.
12. Willie Nelson
| Best Songs | “On the Road Again,” “Always on My Mind,” “Blue Eyes Crying in the Rain,” “Mamas Don’t Let Your Babies Grow Up to Be Cowboys” |
| Notable Albums | *Red Headed Stranger*, *Stardust*, *Shotgun Willie* |
| Awards | Grammy Lifetime Achievement Award, Country Music Hall of Fame, Kennedy Center Honors |
| Key Themes | Freedom, Love, Heartache, Life on the Road |
| Legacy | A true legend in country music, known for his unique voice and rebellious spirit |
Willie Nelson is more than a musician; he is an American icon. His smooth, laid-back voice carried stories of love, freedom, and life on the road. Nelson’s blend of traditional country with jazz, blues, and folk set him apart.
“On the Road Again” became a signature anthem for his free-spirited lifestyle. Even at 90, Nelson continues to perform, inspiring generations with his unmatched charisma and timeless music.
13. Johnny Paycheck
| Best Songs | “Take This Job and Shove It,” “Mr. Lovemaker,” “Me and the IRS” |
| Notable Albums | *Take This Job and Shove It*, *Slide Off of Your Satin Sheets*, *Mr. Lovemaker* |
| Awards | No major awards, but known for his rebellious persona |
| Key Themes | Work Struggles, Rebellion, Heartache |
| Legacy | Known for his rough and defiant attitude, became a working-class hero with “Take This Job and Shove It” |
Johnny Paycheck’s name became synonymous with rebellion. His biggest hit, “Take This Job and Shove It,” became an anthem for workers fed up with their bosses. Paycheck’s music often reflected the struggles of the everyday man.
His rough-around-the-edges persona only added to his appeal. He didn’t shy away from trouble, both in life and in music, cementing his place as a key figure in outlaw country.
14. Margo Price
| Best Songs | “Hurtin’ (On the Bottle),” “Hands of Time,” “Tennessee Song” |
| Notable Albums | *Midwest Farmer’s Daughter*, *That’s How Rumors Get Started*, *All American Made* |
| Awards | Americana Music Awards Emerging Artist of the Year |
| Key Themes | Hardship, Resilience, Social Justice, Rebellion |
| Legacy | One of the most influential modern outlaw country artists, unapologetic and outspoken |
Margo Price brings a fresh voice to outlaw country. Her music covers a range of topics, from personal hardships to social justice. Price’s raw honesty and refusal to fit into the mainstream mold make her a key figure in the modern outlaw movement.
Songs like “Hurtin’ (On the Bottle)” reflect both vulnerability and strength, traits that define her growing legacy.
15. Charley Pride
| Best Songs | “Kiss an Angel Good Mornin’,” “Is Anybody Goin’ to San Antone,” “Mississippi Cotton Picking Delta Town” |
| Notable Albums | *The Best of Charley Pride*, *Just Plain Charley*, *Sings Heart Songs* |
| Awards | Country Music Hall of Fame, Grammy Lifetime Achievement Award |
| Key Themes | Love, Heartache, Struggle, Identity |
| Legacy | First Black country music star, broke racial barriers in the industry |
Charley Pride’s journey in country music was groundbreaking. He overcame racial barriers to become one of the genre’s most beloved voices. With hits like “Kiss an Angel Good Mornin’,” Pride captured hearts with his smooth vocals and heartfelt lyrics.
His career spanned decades, and he remained a trailblazer for Black artists in country music. Pride’s contributions went beyond music, opening doors for those who came after him.
16. Billy Joe Shaver
| Best Songs | “Live Forever,” “Georgia on a Fast Train,” “Honky Tonk Heroes” |
| Notable Albums | *Old Five and Dimers Like Me*, *Honky Tonk Heroes*, *Tramp on Your Street* |
| Awards | Academy of Country Music Poet’s Award |
| Key Themes | Resilience, Hardship, Redemption, Freedom |
| Legacy | Songwriting legend, revered by outlaw country artists for his authentic storytelling |
Billy Joe Shaver’s songs embodied the true outlaw spirit. His simple yet powerful lyrics told stories of hard times and redemption. Shaver’s influence on outlaw country runs deep, with his songs often being covered by other legendary artists.
“Honky Tonk Heroes” is considered one of the key albums that helped define the genre. Despite his personal struggles, Shaver’s music lives on, inspiring countless musicians with its raw honesty.
One of the most surprising stories involved him shooting a man in the face outside a bar in Lorena, Texas, in 2007.
17. Sturgill Simpson
| Best Songs | “Turtles All the Way Down,” “Keep It Between the Lines,” “Brace for Impact (Live a Little)” |
| Notable Albums | *Metamodern Sounds in Country Music*, *A Sailor’s Guide to Earth*, *Sound & Fury* |
| Awards | Grammy Award for Best Country Album |
| Key Themes | Existentialism, Rebellion, Freedom, Self-Reflection |
| Legacy | Genre-defying artist, blending outlaw country with rock and psychedelic elements |
Sturgill Simpson is a modern voice for the outlaw country movement. His refusal to stay within the boundaries of traditional country makes him stand out. Simpson’s mix of country, rock, and psychedelic influences brings a fresh and unique sound to the genre.
Albums like Metamodern Sounds in Country Music challenged expectations, while his Grammy-winning A Sailor’s Guide to Earth showcased his range as both a musician and storyteller.
18. Sammi Smith
| Best Songs | “Help Me Make It Through the Night,” “I’ve Got to Have You,” “The Rainbow in Daddy’s Eyes” |
| Notable Albums | *Help Me Make It Through the Night*, *Lonesome*, *The Toast of ’45* |
| Awards | Grammy Award for Best Country Vocal Performance |
| Key Themes | Love, Heartache, Vulnerability |
| Legacy | One of the few women in the outlaw country movement, known for emotional depth in her songs |
Sammi Smith’s sultry voice and heartfelt delivery made her stand out in the early days of outlaw country. Her rendition of “Help Me Make It Through the Night” became an instant classic. Smith’s ability to convey raw emotion helped define her career.
She was one of the few women who broke into the male-dominated outlaw country scene, leaving a lasting mark with her haunting performances and deep vulnerability.
She was deeply involved in the Native American community and worked to preserve Indigenous culture and rights.
19. Townes Van Zandt
| Best Songs | “Pancho and Lefty,” “If I Needed You,” “For the Sake of the Song” |
| Notable Albums | *Townes Van Zandt*, *Our Mother the Mountain*, *Live at the Old Quarter* |
| Awards | No major awards, but revered as one of the greatest songwriters in country music |
| Key Themes | Loneliness, Despair, Freedom, Redemption |
| Legacy | Known for his poetic songwriting, deeply influential on country and folk musicians |
Townes Van Zandt’s songwriting set him apart as a legend in outlaw country. His lyrics, often filled with melancholy and loneliness, spoke to the deeper emotions many tried to hide. Songs like “Pancho and Lefty” and “If I Needed You” became staples in country music.
Though Van Zandt’s career was marked by struggles with addiction, his music lives on, inspiring countless artists across genres with its timeless beauty and emotional depth.
He once brought a small TV on stage during a performance so he could watch Perry Mason during his set.
20. Hank Williams
| Best Songs | “Your Cheatin’ Heart,” “I’m So Lonesome I Could Cry,” “Hey, Good Lookin'” |
| Notable Albums | *Hank Williams Sings*, *Moanin’ the Blues*, *Ramblin’ Man* |
| Awards | Country Music Hall of Fame, Grammy Lifetime Achievement Award |
| Key Themes | Love, Heartbreak, Loneliness, Struggle |
| Legacy | One of the most influential figures in country music history, credited with laying the foundation for modern country |
Hank Williams is often considered one of the greatest country music artists of all time. His songs, marked by heartbreak and loneliness, became timeless anthems for the genre. “Your Cheatin’ Heart” and “I’m So Lonesome I Could Cry” are just two examples of his ability to tap into deep emotions.
Though his life was cut short at 29, Williams’ influence on country music remains unmatched. His legacy continues to inspire generations of artists and fans alike.
Hank Williams is widely recognized for his iconic contributions to country music, but something truly unique about him is his connection to the “Luke the Drifter” pseudonym. Williams would release more gospel and moralistic songs under this name, separate from his mainstream releases.
FAQs
How did Billy Joe Shaver get his start in songwriting?
Billy Joe Shaver started his career as a songwriter after landing a job at a songwriting studio in Nashville. He wrote hits for other artists, including Waylon Jennings’ Honky Tonk Heroes, which became a cornerstone of outlaw country. Shaver’s writing was raw and honest, drawing from his own life experiences, making him a significant influence in the genre.
What inspired Sturgill Simpson to make his album A Sailor’s Guide to Earth?
Sturgill Simpson wrote A Sailor’s Guide to Earth as a letter to his newborn son. Having served in the Navy himself, the album’s themes revolve around life lessons and reflections. It was also his way of exploring fatherhood while incorporating his diverse musical influences, including country, rock, and even Motown.
What was Sammi Smith’s relationship with Kris Kristofferson?
Sammi Smith is best known for her version of “Help Me Make It Through the Night,” written by Kris Kristofferson. Kristofferson once said that Sammi’s interpretation of his song was so powerful that it became the definitive version. They remained close friends throughout their careers.
Why was Townes Van Zandt considered so influential despite limited commercial success?
Townes Van Zandt’s music, particularly his songwriting, is revered by musicians across many genres, even though he never achieved major commercial success during his lifetime. His influence comes from his lyrical depth and raw emotional storytelling. Artists like Bob Dylan and Willie Nelson have cited him as one of the greatest songwriters ever.
What made Hank Williams’ final performance so memorable?
Hank Williams’ last performance, in December 1952, was filled with tension as he was reportedly in poor health and unable to complete his set. It was an emotional night, as fans witnessed one of the final moments of Williams’ troubled but legendary career. He died just weeks later on New Year’s Day 1953.
Last Words
Outlaw country music has always been more than just a genre. It is a way of life marked by independence, rebellion, and raw honesty. The artists who shaped this movement lived hard, sang from the soul, and left legacies that extended far beyond their music. From Billy Joe Shaver’s wild life and legendary songwriting to Hank Williams’ untimely end, each figure added something unique to the outlaw country legacy.
