Playlist: Outlaw Country
Outlaw country is as much a movement as it is a genre. It began as a rebellion against the mainstream country sound and has since produced some of the most beloved and distinctive artists in the genre, all united by a disdain for the establishment.
Written by Joseph Gonzalez
Illustrated by Luke Rathburn
Outlaw country was an inevitable reaction to the constraints of mainstream country music. Emerging as an outcry from rebellious country musicians starving for authenticity, the genre produced an uncompromising, rough-edged sound that continues to reverberate today, pioneered by renegades like Merle Haggard, Willie Nelson, Kris Kristofferson, John Prine, and Townes Van Zandt.
Influenced as much by soul, Tejano, and rock and roll music as much as traditional country and folk, outlaw country often blends styles in ways that transcend regional or cultural boundaries. Culturally, it resembles the counterculture of Haight-Ashbury, the San Francisco headquarters of 1960s hippiedom, as much as it does the rural South.
Whether driven by lively, funk-based horns and keys, or the plaintive, longing strums of an acoustic guitar, outlaw country is defined by its unabashed rejection of the establishment and its uncompromising sincerity.
The Roots: Johnny Cash and Merle Haggard
The genre’s earliest musical manifestations began in the mid-1950s with Johnny Cash’s “Folsom Prison Blues,” a rockabilly song infused with Cash’s signature country twang. The song’s remorseful narrator, a man serving time for murder in Folsom State Prison, reflects on the choices that left him to his fate.
The narrator’s disregard for authority, represented by his mother, leads him to his inevitable fate of confinement. He bitterly longs for his escape as he imagines the “rich folks eatin’ in a fancy dining car,” his mind plagued with fantasies of boarding a train and being free again.
Despite the melancholic themes, the song is anything but sad, as Cash enthusiastically sings and carries the fast-paced rhythm with his staccato guitar strums. The lead guitarist punctuates the lyrically sullen verses with upbeat guitar solos. The almost celebratory and contradictory tone of the music serves as a rebellion against the narrator’s situation — a conscious choice to maintain his character and humanity rather than wallow in self-defeat.
Cash’s live performance at Folsom Prison in 1968, immortalized in the live album, At Folsom Prison, cemented his role as a pioneer in the genre. The recording, in which “Folsom Prison Blues” stood as an obvious highlight, was a radical act — performing for a crowd of inmates — and a key moment of solidarity with society's outcasts.
Cash performed at several prisons dating back to 1958 — when he famously performed in front of future country legend, Merle Haggard, at San Quentin — and would go on to release three more live albums recorded in prisons. Cash lent humanity to people who are often dehumanized, unafraid to portray a morally complicated outlaw, which inspired Haggard. In 1968, Haggard released “Mama Tried,” a heartbreakingly honest anthem about a prisoner lamenting his choices. Unlike Cash’s more defiant outlaw, Haggard’s character in this track is tragic in his remorseful acknowledgment of his mistakes. The song carries extra weight because Haggard had the lived experience of serving prison time, though not the life sentence the narrator receives:
“And I turned twenty-one in prison, doing life without parole / No one could steer me right, but Mama tried,” Haggard sings, supported by a buoyant bassline and folksy guitar lines
The Rise: Willie Nelson and Waylon Jennings
As the 1960s gave way to the 1970s, two rising country stars, Willie Nelson and Waylon Jennings, decided to break away from the artistically constraining Nashville music scene, despite their modest commercial success. In 1972, Nelson left Nashville for the less corporate scene of Austin, and Jennings rejected a major record deal from RCA Records. They decided that if they kept making music, it would be on their own terms.
With the help of manager Neil Geshen, Jennings and Nelson gained creative control and signed record deals that gave them the creative control they desired and allowed them to fully express their outlaw spirits. Nelson’s Shotgun Willie (1973) marked a new chapter in his career, blending country, soul, and funk with unapologetic lyricism.
“You can’t make a record if you ain’t got nothin’ to say,” Nelson sings in the album’s title track, which was inspired by an incident where the singer threatened his daughter’s abusive husband with a shotgun.
The song is an eclectic mix of sounds, featuring a steel pedal guitar with a horn-like effect, actual horns, flourishes of grand piano, and solos from both electric and acoustic guitars. Together, these elements create a groovy, slightly wacky version of Nelson’s singular vision. Nelson’s voice in the song is wry and spoken, rather than musical. It doesn’t sound like he’s imitating anyone else. His distinctiveness is stark because he’s not trying to be a traditionally good singer or fit himself into a box — he simply imbues his own plainspoken style into the track.
Nelson’s embracement of the soul and funk sound he’d only briefly and more timidly explored in the past is exemplified in songs like “Shotgun Willie”, and “Whiskey River.” These songs are given room to groove with their rollicking bass lines and background singers.” He also showcases his talent for the traditional country ballads he is familiar with in songs like, “So Much to Do” and “Sad Songs and Waltzes.”
Shotgun Willie’s cover art also marked a turning point in Nelson’s public image, as it is the first to feature a bearded Willie Nelson, with the musician flashing a smile through both barrels of a shotgun — an image he would carry for the rest of his career.
With the influence of Nelson and music venues like the Armadillo World Headquarters, Austin became a hub for the outlaw country movement, attracting emerging outlaw singer-songwriters like Guy Clark, Jerry Jeff Walker, Doug Sahm, Billie Joe Shaver, Steve Earle, and Townes Van Zandt. These musicians, along with bands like Commander Cody and His Lost Planet Airmen and the New Riders of the Purple Sage, captured the spirit of outlaw country by embodying the unruly, unserious, drug-using, and self-loathing vagabond character of the outlaw archetype.
The spirit ran in direct contrast to the polished image of artists associated with the “Nashville Sound” and Countrypolitan genres, who geared their music towards pop and mainstream appeal, playing it safe to avoid upsetting anyone and jeopardizing radio play.
Outlaw musicians made music knowing it probably wouldn’t top the charts. They cared less about commercial success and more about artistic integrity.
The Storytellers: Kris Kristofferson and John Prine
Around the same time, in Nashville, Johnny Cash’s endorsement of Kris Kristofferson helped the artist reach a wider audience. Kristofferson’s self-titled 1970 debut album would become a masterclass in introspective storytelling, bound together by catchy choruses and diverse instrumentation, covering themes of carnality, police brutality, and isolation.
In the unforgettable album closer, “Sunday Mornin’ Comin’ Down,” the lyrics depict a depressed man who decides to wander the lonely city streets on a Sunday morning.
“Well, I woke up Sunday morning / With no way to hold my head that didn't hurt / And the beer I had for breakfast wasn't bad / So I had one more for dessert,” Kristofferson begins, his anguished voice backed by a melancholic chord progression and soft percussion.
The chorus kicks up the energy, adding a fuller drum beat and loud percussive keys. “On the Sunday morning sidewalks / Wishing, Lord, that I was stoned / ‘Cause there's something in a Sunday / That makes a body feel alone,” he sings, his voice growing louder but still carrying the same anguish from the beginning.
With this song, Kristofferson helped popularize the “wanderer” character in this new age of country music. Reflecting the life of many struggling singer-songwriters, the narrator is lost and lonely — both mentally and physically. He attempts to escape by using drugs and aimless wandering until he rediscovers the “somethin' / That [he’d] lost somehow, somewhere along the way.”
Meanwhile, with the support of Kristofferson, 24-year-old country singer-songwriter John Prine released his first album, John Prine, in 1971. Prine represented a political rebellion, with many of his songs carrying a politically charged tone, with songs like “Sam Stone” serving as a direct response to the presidency of Richard Nixon and the Vietnam War. This track depicts a Vietnam veteran suffering from major psychological and physical injuries, failed by the American system.
“But life had lost its fun and there was nothing to be done / But trade his house that he bought on the G.I. Bill / For a flag-draped casket on a local hero’s hill / There's a hole in Daddy's arm where all the money goes / Jesus Christ died for nothin', I suppose,” Prine dejectedly laments, his voice accompanied by a strange and melodic organ-like melody layered atop the subdued picking of an acoustic guitar.
Though many early outlaw country albums were commercial failures, the movement continued to expand.
An Emerging Community of Rebels
By the mid-1970s, outlaw country saw an influx of new singular talents like Joe Ely, Ray Wylie Hubbard, Terry Allen, Emmylou Harris, and David Allan Coe.
These artists continued to rebel against the guarded and refined sound of the mainstream country scene, creating expressive songs that personified the reckless and revolutionary spirit of the movement, both in their music and personal lives.
David Allen Coe played on the streets of Nashville after spending time in prison. Terry Allen was an accomplished visual artist before his unique piano-centric and satirical sound, surreally detailing the quirks of rural Texas.
The scene thrived on collaboration and community. The musicians knew each other, played together, and covered one another, often popularizing lesser-known songs. For instance, Nelson and Haggard legitimized Van Zandt’s “Pancho and Lefty” with their 1983 cover. While their version is less intimate and starts with a mildly out-of-place disco-like intro, Nelson and Haggard’s voices blend harmoniously with the melody of the song, telling the story of a cowboy and a Mexican bandit.
In 1985, The Highwaymen — a supergroup composed of Cash, Jennings, Nelson, and Kristofferson — formed and recorded its first of three albums, where it explored a bigger, ‘80s-inspired stadium sound.
Its biggest hit, “Highwaymen,” a cover of a Jimmy Webb song, became an anthem about the eternal souls of four outlaws. Each member sang a verse, the melody of their voices accompanied by the sustained strings and synth chords.
“Perhaps I may become a highwayman again / Or I may simply be a single drop of rain / But I will remain / And I'll be back again,” Cash sings in the last verse, foreshadowing the idea of his spirit persisting after his death.
1990s and Beyond: Outlaw Country Persists
Going into the ‘90s, even more outlaw-inspired artists rose to prominence as the original scene aged. Artists like Robert Earl Keen and Lucinda Williams carried the torch, while the original outlaw icons of the ‘60s and ‘70s were still creating new music. Keen released his defining song, “The Road Goes on Forever,” which encapsulates the storytelling quality of outlaw country. The track tells the tale of two lovers breaking the law, “Where a lawman tackled Sonny and was readin’ him his rights / She stepped out in the alley with a single-shot .410 / The road goes on forever and the party never ends.” Lucinda Williams, a well-respected songwriter, broke into commercial success with her album, Car Wheels on a Gravel Road, which received critical acclaim for its “evocations of rural rootlessness — about juke joints, macho guitarists, alcoholic poets, loved ones locked away in prison,” as music critic Robert Christgau reviewed in Rolling Stone in 1998.
Keen’s and Williams’ raw voices and frank lyricism endeared them to both existing fans and artists within the scene.
As the original generation of outlaw country artists aged, often becoming more introspective at the same time, their influence. lives on in artists like Sturgill Simpson, Jason Isbell, Margo Price, and Tyler Childers. The original outlaw country ethos continues to inspire a new generation.
The movement has also been passed down directly from parent to offspring. Tommy Prine, the son of John Prine, released his first album in 2023. Steve Earle’s son, Justin Townes Earle (named after Steve Earle’s good friend Townes Van Zandt) released seven albums before tragically passing away in 2020. Lukas Nelson, the son of Willie Nelson, continues to build his legacy and status with his band, Promise of the Real, and duets with his father. In duets like “Just Outside of Austin,” the father-son duo flawlessly encapsulates a multi-generational example of the sentimentality often found in the genre.
“Just outside of Austin / High as I've ever been / Just outside of Austin / I think I fell in love with you again,” Lukas sings, accompanied by the iconic flourishes of Willie’s aging guitar, Trigger. Lukas Nelson’s voice, alongside Willie’s, speaks to the cyclical nature of life and music, capturing the timelessness of the outlaw spirit.
Emerging artists continue to push back against the mainstream sound, but with a more modern twist. They maintain the essence of those on the outer edges of society, unafraid to offend those who might be upset with their expression.
Sturgill Simpson draws on traditional country and rock, expanding his own sound with spacey production to comment on topics like psychedelics and spirituality. His presence as an outsider in popular country music was most poignantly exemplified when he stood outside the 2017 Country Music Awards raising funds for the ACLU by busking.
The year prior, when the Academy of Country Music Awards created a “Spirit Award” in honor of the late Merle Haggard, Simpson responded in a Facebook post, “If the ACM wants to actually celebrate the legacy and music of Merle Haggard, they should drop all the formulaic cannon fodder bull — they’ve been pumping down rural America’s throat for the last 30 years.”
Margo Price channels her authentic experiences as a woman and mother into her songs, touching on potentially divisive subjects like female beauty standards and abortion. She’s not afraid to write about vulnerable and personal topics, from motherhood and postpartum depression to the grief of losing her son. Her mission of fearlessly portraying authenticity in the form of country music sets her apart from artists who trade hollow messaging for career safety, and connects her with the pioneers of outlaw country.
Whether it’s Simpson’s strong endorsement of psychedelics and social justice or Price’s feminist messaging, current outlaw artists continue to challenge the status quo. While the sound may evolve with the times, the heart of the genre pushes eternally forward as generations come and go.
Legacy
The outlaw country movement is an unstoppable and necessary force both musically and sociopolitically. It brought together artists and musical styles that were previously diametrically opposed, creating a sound and scene that perfectly characterized the complicated American South.
The movement will endure as long as there’s something to rebel against, somewhere to escape to, and something to long for. (And, of course, a Pedal steel guitar.)
So, dive into this disobedient playlist, and remember the words of Robert Earl Keen: "The road goes on forever and the party never ends.”