Back in Time Today
Outlaw country was more than a sound—it was a way of life. Born from rebellion, independence, and a refusal to play by Nashville’s rules, the movement brought raw truth, grit, and swagger to country music.
These 27 songs capture the spirit of the outlaws who changed the genre forever.
1. Mama Tried – Merle Haggard
Merle Haggard’s “Mama Tried” is a semi-autobiographical anthem that echoes with regret and rebellion. The song’s straightforward honesty and rich storytelling pull you into a world where a mother’s love fights against a life of crime.
Haggard’s voice, gravelly yet tender, paints a vivid picture of a man reflecting on choices that led him down a wayward path. With a melody that sticks and lyrics that linger, it’s a song that resonates well beyond its outlaw origins. It’s not just a tale of personal failure; it’s a universal story of human struggle.
2. Luckenbach, Texas (Back to the Basics of Love) – Waylon Jennings
Waylon Jennings takes us to the laid-back, nostalgic world of “Luckenbach, Texas,” where simplicity and genuine connections matter more than material wealth. The gentle strumming of guitars and Jennings’ soothing drawl invite listeners to escape the chaos of modern life and embrace a simpler existence.
This song isn’t just a call back to basics; it’s a reminder to cherish love and authenticity. As the chorus swoons, you can almost feel the warm Texas breeze and the camaraderie of small-town life. It’s a timeless invitation to slow down and savor life’s true pleasures.
3. Whiskey River – Willie Nelson
“Whiskey River” by Willie Nelson is a boozy, unfiltered staple of outlaw country that flows with raw emotion and intoxicating rhythm. The song’s swirling melodies and powerful vocals capture the essence of escapism and heartache.
Nelson’s iconic voice, rich and full of character, draws you down into the depths of sorrow and redemption. With every note, you can almost taste the whiskey and feel the haze of a honky-tonk night. This track embodies all the grit and passion that define the outlaw spirit. It’s a musical journey worth getting lost in.
4. Are You Sure Hank Done It This Way – Waylon Jennings
Waylon Jennings’ “Are You Sure Hank Done It This Way” boldly critiques the polished Nashville sound with unflinching honesty. With biting lyrics and a driving beat, Jennings questions the direction of modern country music, invoking the spirit of Hank Williams as a beacon of authenticity.
The song’s rebellious tone and catchy melody make it a standout anthem of defiance. Jennings challenges listeners to embrace real, raw music over commercial polish. This track isn’t just a critique; it’s a call to honor the roots and soul of country music.
5. Good Hearted Woman – Waylon Jennings & Willie Nelson
“Good Hearted Woman” by Waylon Jennings & Willie Nelson is an ode to the strong women behind the men, celebrating their loyalty and love amidst the chaos of the outlaw lifestyle. The upbeat tempo and heartfelt lyrics convey a story of admiration and gratitude.
Jennings and Nelson’s harmonies weave together seamlessly, creating a powerful tribute that resonates with anyone who’s ever loved or been loved despite imperfections. It’s a song that honors the unsung heroes who stand by their partners through thick and thin, capturing the spirit of enduring devotion.
6. If That Ain’t Country – David Allan Coe
David Allan Coe’s “If That Ain’t Country” paints a gruff and gritty portrait of rural life, filled with authenticity and raw emotion. The song’s vivid imagery and Coe’s rugged voice transport listeners to a world where hard work and simple pleasures define existence.
Each verse tells a story, from childhood memories to lessons learned on the road. Coe’s unapologetic attitude and genuine storytelling make this song a hallmark of the outlaw genre. It’s a musical journey through the heartland, rich with tradition and unyielding spirit.
7. Ride Me Down Easy – Billy Joe Shaver
Billy Joe Shaver’s “Ride Me Down Easy” is a road-weary ballad imbued with quiet defiance and a longing for peace. With simple yet poignant lyrics, Shaver captures the essence of a life lived on the edge but yearning for solace.
The melody flows like a gentle breeze, carrying with it tales of hardship and endurance. Shaver’s voice, weathered and wise, offers a tender reflection on the journey of life. This song embodies the outlaw spirit’s resilience and desire for contentment amidst chaos and uncertainty.
8. Copperhead Road – Steve Earle
Steve Earle’s “Copperhead Road” is a bootlegging tale turned country-rock anthem, filled with gritty realism and a rebellious edge. The driving beat and Earle’s raw vocals create an intense atmosphere as the story unfolds.
Earle takes listeners on a wild ride through generations of moonshiners and outlaws, weaving a narrative that’s both thrilling and cautionary. The powerful imagery and unforgettable chorus make it a staple of the outlaw genre. It’s a song that resonates with anyone who’s ever dared to defy the norm.
9. Pancho and Lefty – Townes Van Zandt / Willie Nelson & Merle Haggard
“Pancho and Lefty,” originally by Townes Van Zandt, takes on new dimensions with Willie Nelson & Merle Haggard’s rendition. This mysterious folk story is infused with deep outlaw soul, exploring themes of betrayal and loss.
Nelson and Haggard’s voices blend perfectly, creating a haunting narrative that captures the imagination. The song’s melancholy tone and vivid storytelling leave listeners pondering the fate of its enigmatic characters. It’s a timeless piece that embodies the essence of the outlaw tradition, where legends are born, and mysteries remain unsolved.
10. The Ride – David Allan Coe
David Allan Coe’s “The Ride” is a ghostly encounter with Hank Williams that sets the tone for this eerie classic. The song’s haunting melody and Coe’s evocative vocals transport listeners to a metaphysical journey.
As the spectral ride unfolds, Coe receives wisdom and insight from the legendary Hank Williams, creating a bridge between past and present. The blend of mystery and nostalgia makes this track a standout in the outlaw genre. It’s a chilling reminder of the legends who shaped country music’s rebellious spirit.
11. I’m the Only Hell (Mama Ever Raised) – Johnny Paycheck
Johnny Paycheck serves up bad-boy swagger wrapped in a mama’s warning with “I’m the Only Hell (Mama Ever Raised).” The song’s rollicking rhythm and Paycheck’s gritty voice deliver a tale of wild living and maternal disappointment.
With a twinkle in his eye, Paycheck embraces his reputation, reveling in the defiance that defines him. The catchy chorus and rebellious spirit make it a quintessential outlaw anthem. It’s a playful yet poignant reflection on living life on one’s own terms, no matter the consequences.
12. Ramblin’ Man – Hank Williams Jr.
Hank Williams Jr.’s “Ramblin’ Man” is a declaration of inherited wildness and a life lived on the road. The song’s driving rhythm and Williams’ powerful voice encapsulate the restless spirit of an eternal traveler.
With vivid lyrics and a catchy melody, Williams pays homage to his father’s legacy while carving his own path. The song’s energy and passion make it a rallying cry for those who embrace freedom and adventure. It’s an anthem for anyone who’s ever felt the call of the open road.
13. My Heroes Have Always Been Cowboys – Willie Nelson
Willie Nelson’s “My Heroes Have Always Been Cowboys” is reflective, romantic, and heartbreakingly honest. The song’s gentle melody and Nelson’s tender vocals paint a picture of admiration for the rugged, independent spirit of cowboys. As the verses unfold, Nelson explores themes of heroism and solitude, capturing the essence of a lifestyle that’s both noble and isolating.
It’s a song that resonates with those who value freedom and authenticity above all else. A timeless tribute to the cowboy ethos, it’s a melody filled with longing and reverence.
14. Long Haired Country Boy – Charlie Daniels Band
The Charlie Daniels Band’s “Long Haired Country Boy” is an anthem of nonconformity and good ol’ boys doing it their way. The song’s upbeat tempo and Daniels’ spirited performance create a lively celebration of individuality.
With lyrics that embrace a carefree lifestyle, the track invites listeners to shrug off societal expectations and live authentically. The fiddle-driven melody adds a playful touch, making it impossible not to tap your feet. It’s a joyful reminder to embrace who you are, no matter what others think.
15. Lonesome, On’ry and Mean – Waylon Jennings
Waylon Jennings’ “Lonesome, On’ry and Mean” presents a defiant portrait of a life lived rough and on the edge. The song’s gritty lyrics and driving beat paint a vivid picture of rebellion and solitude.
Jennings’ commanding voice and relentless energy make this track an anthem for those who march to the beat of their own drum. It’s a celebration of the outlaws who refuse to conform, even when facing adversity. This song captures the essence of the outlaw spirit, where freedom and defiance reign supreme.
16. I Think I’ll Just Stay Here and Drink – Merle Haggard
Merle Haggard’s “I Think I’ll Just Stay Here and Drink” is barroom blues in peak outlaw form. The song’s laid-back rhythm and Haggard’s smooth voice create a perfect backdrop for a night spent in quiet contemplation.
With lyrics that speak to the heart of anyone who’s ever sought solace in a bottle, it’s a track filled with both melancholy and comfort. Haggard’s storytelling shines through, making it an unforgettable tune that resonates with anyone who’s ever embraced the barroom refuge.
17. You Never Even Called Me by My Name – David Allan Coe
David Allan Coe’s “You Never Even Called Me by My Name” is a satirical, self-aware tribute to classic country tropes. The song’s witty lyrics and Coe’s charismatic delivery poke fun at the clichés that define country music.
With its catchy chorus and playful tone, the song invites listeners to enjoy the humor and charm of storytelling. Coe’s ability to balance sarcasm and sincerity makes this track a standout in the outlaw genre. It’s a delightful reminder not to take life—or music—too seriously.
18. Honky Tonk Heroes – Waylon Jennings
Written by Billy Joe Shaver, “Honky Tonk Heroes” became a blueprint for outlaw country through Waylon Jennings’ rendition. The song’s raw energy and Jennings’ commanding voice capture the essence of the honky-tonk lifestyle.
With vivid storytelling and unforgettable melodies, this track pays tribute to the renegades who shaped the genre. It’s a celebration of the music and the people who dared to be different, leaving an indelible mark on country history. This song embodies the heart and soul of the outlaw movement.
19. Ride Through the Country – Colt Ford feat. John Michael Montgomery
Colt Ford’s “Ride Through the Country,” featuring John Michael Montgomery, offers a modern twist on outlaw spirit and country grit. The song’s infectious beat and lively vocals create a fun-filled journey through rural landscapes.
With lyrics celebrating the joys of country living, it’s a track that resonates with anyone who loves the outdoors and the simple life. Ford and Montgomery’s collaboration brings a fresh perspective to the genre, honoring traditions while embracing contemporary influences. It’s a joyful ride worth taking.
20. Ain’t Livin’ Long Like This – Rodney Crowell
Rodney Crowell’s “Ain’t Livin’ Long Like This” is a high-octane rejection of the good life gone wrong. The song’s fast-paced rhythm and Crowell’s fiery delivery capture the urgency of breaking free from a destructive path.
With lyrics that tell a tale of misadventure and redemption, it’s a powerful anthem for those who refuse to be trapped by circumstance. Crowell’s passionate performance makes it a standout in the outlaw genre, filled with grit and determination. This track embodies the restless spirit of rebellion.
21. Guitars, Cadillacs – Dwight Yoakam
Dwight Yoakam’s “Guitars, Cadillacs” exudes neo-traditionalist swagger with a Bakersfield bite. The song’s twangy guitar riffs and Yoakam’s distinctive voice create a sound that’s both fresh and timeless.
With lyrics that explore themes of heartbreak and resilience, the track offers a classic country vibe with a modern twist. Yoakam’s ability to blend tradition with innovation makes this song a hallmark of the genre. It’s a musical journey that resonates with anyone who appreciates authenticity and style.
22. Trucker’s Speed – Fred Eaglesmith
Fred Eaglesmith’s “Trucker’s Speed” is a dark, frenetic dive into desperation and movement. The song’s relentless pace and Eaglesmith’s gritty vocals create an atmosphere of urgency and tension.
With vivid storytelling and intense energy, the track captures the chaos of life on the road and the relentless pursuit of freedom. Eaglesmith’s unique style and powerful delivery make it a standout in the outlaw genre. It’s a thrilling ride through the underbelly of country life, full of grit and raw emotion.
23. Outlaw Women – Hank Williams Jr.
Hank Williams Jr.’s “Outlaw Women” celebrates the tough and independent women of the outlaw world. The song’s upbeat tempo and Williams’ bold delivery pay tribute to those who defy societal norms with grace and grit.
With lyrics that highlight strength and resilience, the track is a powerful anthem for women who live life on their terms. Williams’ energetic performance and catchy melody make it a standout in the genre. It’s a song that honors the spirit of freedom and individuality.
24. Ain’t No God in Mexico – Waylon Jennings
Waylon Jennings’ “Ain’t No God in Mexico” is a dusty, grimy tale full of tension and existential reflection. The song’s haunting melody and Jennings’ deep voice create a sense of unease and introspection.
With lyrics that explore themes of disillusionment and searching, it’s a track that resonates with those who question the world around them. Jennings’ unique storytelling and atmospheric sound make it a standout in the outlaw genre. It’s a captivating journey through the heart of uncertainty.
25. Mama’s Don’t Let Your Babies Grow Up to Be Cowboys – Waylon & Willie
Waylon & Willie’s “Mama’s Don’t Let Your Babies Grow Up to Be Cowboys” is a weary but proud anthem of life on the edge. The song’s heartfelt lyrics and harmonies capture the rugged, independent spirit of cowboy life.
With a touch of nostalgia and a hint of warning, it’s a track that resonates with both dreamers and realists. Jennings and Nelson’s performance is a masterful blend of emotion and storytelling, making it an enduring classic in the outlaw genre. It’s a song that speaks to the heart of rebellion and freedom.
26. The Road Goes on Forever – Robert Earl Keen
Robert Earl Keen’s “The Road Goes on Forever” is a modern outlaw epic of crime, love, and legend. The song’s vivid storytelling and Keen’s engaging delivery create a captivating narrative that pulls listeners in.
With twists and turns that keep you on the edge of your seat, it’s a track that embodies the spirit of adventure and unpredictability. Keen’s ability to weave complex characters and plots makes this song a standout in the genre. It’s a thrilling journey through the highs and lows of outlaw life.
27. Choctaw Bingo – James McMurtry
James McMurtry’s “Choctaw Bingo” offers Southern storytelling at its most twisted and gripping. The song’s intricate lyrics and McMurtry’s commanding voice create a vivid tapestry of eccentric characters and wild escapades.
With a driving beat and dark humor, it’s a track that invites listeners into a world that’s both familiar and strange. McMurtry’s unique perspective and storytelling prowess make this song a standout in the outlaw genre. It’s an unforgettable ride through the quirks and chaos of Southern life.