Outlaw country, with its rebellious spirit, raw storytelling, and gritty sound, has produced some legendary hits. However, beyond the well-known tracks of icons like Willie Nelson, Waylon Jennings, and Johnny Cash, there exists a treasure trove of songs that haven’t received the attention they deserve. This collection highlights 20 such gems, capturing the essence of the outlaw movement and showcasing the depth and diversity of its musical offerings.
1. “Black Rose” – Waylon Jennings (1973)
“Black Rose” by Waylon Jennings is a standout track from 1973. This song weaves its magic with a dark, bluesy vibe, making it a must-listen for any outlaw country aficionado. In the first verse, Jennings captivates with his gravelly voice, drawing listeners into a world of melancholy and introspection. The chorus is a masterclass in songwriting, showcasing Waylon’s ability to blend traditional country elements with a rebellious edge. It’s a perfect representation of his signature sound. Each note and lyric tells a story, inviting listeners to explore the depths of human emotion.
2. “Ride Me Down Easy” – Billy Joe Shaver (1973)
“Ride Me Down Easy” by Billy Joe Shaver is a beautifully crafted piece from 1973 that tugs at the heartstrings. Shaver, known for his storytelling prowess, delivers a narrative full of longing and reflection. The song’s gentle melody is complemented by lyrics that speak to life’s transient nature and the desire for a peaceful journey. In the chorus, Shaver’s voice resonates with sincerity, offering comfort and understanding. Each verse unfolds like a chapter in a book, rich in emotion and introspection. The simplicity of its arrangement enhances its timeless appeal, making it unforgettable.
3. “The Real Me” – Shooter Jennings (2005)
“The Real Me” by Shooter Jennings from 2005 brings a modern touch to the outlaw genre. The track’s introspective lyrics and rebellious spirit resonate with both new and seasoned fans. From the opening riff, Jennings sets the tone with a hard-hitting sound that commands attention. His voice, raw and unfiltered, explores themes of identity and authenticity. Within the verses, he navigates personal struggles, offering a glimpse into his world. The energy of the music mirrors the intensity of the lyrics, creating a captivating experience. Its boldness and honesty make it a standout in contemporary outlaw country.
4. “Me and Paul” – Willie Nelson (1971)
“Me and Paul” by Willie Nelson is a heartfelt ode to friendship and life on the road. Released in 1971, the song chronicles Nelson’s adventures with his drummer, Paul English. The storytelling is vivid, painting a picture of camaraderie and the challenges of touring. In the chorus, Nelson’s voice carries warmth and nostalgia, reflecting on shared memories. Each verse offers a snapshot of their journey, highlighting both triumphs and trials. The simplicity of the instrumentation complements the song’s narrative, allowing the lyrics to shine. It’s a tribute to enduring friendship, capturing the essence of their bond.
5. “Slow Rollin’ Low” – Jerry Jeff Walker (1974)
“Slow Rollin’ Low” by Jerry Jeff Walker is a soulful ballad from 1974 that exudes a sense of melancholy and reflection. The song’s gentle rhythm and soothing melody create an atmosphere of introspection. Walker’s vocals are tender, delivering lyrics that speak to the passage of time and the longing for a simpler life. The chorus is a blend of wistfulness and hope, resonating with listeners on a personal level. Throughout the track, the instrumentation enhances its emotional depth, weaving a tapestry of sound that lingers in the mind. It’s a testament to Walker’s artistry and storytelling.
6. “I Had to Get Drunk Last Night” – Gary Stewart (1978)
“I Had to Get Drunk Last Night” by Gary Stewart is a poignant honky-tonk lament from 1978 that captures raw emotion. Stewart’s powerful vocals convey a sense of vulnerability, drawing listeners into a world of heartache and regret. The song’s melody is both haunting and captivating, perfectly complementing the narrative. In the verses, Stewart reflects on the pain of lost love, each word resonating with authenticity. The chorus, filled with longing, leaves a lasting impression, inviting empathy and understanding. Its emotional intensity and honest storytelling make it a standout track in Stewart’s discography.
7. “T for Texas (Blue Yodel No. 1)” – Waylon Jennings (1976)
Waylon Jennings’ rendition of “T for Texas (Blue Yodel No. 1)” is a masterful homage to Jimmie Rodgers. Released in 1976, Jennings infuses the classic with his outlaw-country flair, offering a fresh take that honors the original. His commanding vocals and powerful guitar work create a dynamic sound that captivates audiences. The song’s energy is infectious, drawing listeners into its lively rhythm. Throughout the track, Jennings showcases his musical prowess, blending traditional elements with modern sensibilities. It’s a celebration of the genre’s roots and a testament to Jennings’ ability to reinterpret classics with authenticity.
8. “Ain’t No God in Mexico” – Billy Joe Shaver (1973)
“Ain’t No God in Mexico” by Billy Joe Shaver is a gritty, road-worn tune that exemplifies his storytelling mastery. Released in 1973, this song delves into themes of disillusionment and survival. Shaver’s voice, raw and compelling, draws listeners into a narrative rich with imagery and emotion. The verses paint a vivid picture of life’s challenges, while the chorus offers a poignant reflection on faith and resilience. The simplicity of the arrangement allows the lyrics to shine, creating a powerful connection with the audience. It’s a testament to Shaver’s ability to craft songs that resonate deeply.
9. “Living on the Losin’ End” – Jessi Colter (1975)
“Living on the Losin’ End” by Jessi Colter is a soulful track from 1975 that showcases her unique blend of vulnerability and strength. Colter’s expressive vocals convey a sense of longing and introspection, inviting listeners into her world. The song’s melody, gentle yet powerful, underscores the emotional depth of the lyrics. Each verse unfolds with grace, offering insights into love and loss. The chorus, filled with poignant reflection, lingers in the mind long after the song ends. Colter’s artistry shines through, making this an essential listen for fans of outlaw country and beyond.
10. “Honky Tonk Heroes” – Waylon Jennings (1973)
Written by Billy Joe Shaver, “Honky Tonk Heroes” is a cornerstone of the outlaw country movement. Released in 1973, Waylon Jennings’ rendition is a celebration of the genre’s rebellious spirit. Jennings’ powerful vocals and gritty guitar work bring the song to life, creating an anthem for a generation of outsiders. The verses unfold with a raw honesty, capturing the essence of life on the fringes. In the chorus, Jennings’ voice resonates with defiance and pride, embodying the heart of the outlaw ethos. It’s a timeless track that continues to inspire and connect with listeners today.
11. “Lonesome On’ry and Mean” – Steve Young (1972)
Steve Young’s “Lonesome On’ry and Mean” is a quintessential outlaw anthem released in 1972. This original version, later popularized by Waylon Jennings, captures the raw, untamed spirit of the genre. Young’s vocals, gritty and emotive, convey a sense of wandering and defiance. The song’s melody, both haunting and invigorating, underscores the intensity of the lyrics. Each verse tells a story of resilience and survival, resonating with those who live outside conventional norms. The chorus, filled with determination, echoes the timeless struggle for freedom and authenticity. It’s a landmark track that defines the outlaw movement.
12. “Omaha” – Waylon Jennings (1973)
“Omaha” by Waylon Jennings is a deep cut from 1973 that showcases his storytelling prowess. This track delves into themes of longing and escape, painting a vivid picture of life’s trials and triumphs. Jennings’ voice, rich and commanding, draws listeners into the narrative, offering a glimpse into the protagonist’s journey. The song’s melody, a blend of traditional country and modern influences, creates a captivating soundscape. In the chorus, Jennings’ vocals soar, embodying the yearning for something more. It’s a testament to his ability to craft songs that resonate deeply, leaving a lasting impact on audiences.
13. “We Had It All” – Kris Kristofferson (1973)
Kris Kristofferson’s “We Had It All” is a deeply emotional ballad from 1973 that explores themes of love and loss. Kristofferson’s soulful vocals convey a sense of nostalgia and longing, drawing listeners into the story. The song’s melody, both haunting and beautiful, enhances the emotional depth of the lyrics. Each verse unfolds with grace, capturing the essence of a relationship that once was. In the chorus, Kristofferson’s voice resonates with sincerity, offering a poignant reflection on what’s been lost. It’s a timeless track that speaks to the heart, leaving a lasting impression on all who listen.
14. “Ramblin’ Man” – Hank Williams Jr. (1979)
Hank Williams Jr.’s “Ramblin’ Man” from 1979 is a testament to the restless spirit of the outlaw ethos. This rebellious anthem, with its bluesy groove and powerful lyrics, captures the essence of life on the road. Williams Jr.’s distinctive voice conveys a sense of freedom and adventure, inviting listeners to embrace the journey. The song’s melody, both dynamic and infectious, enhances its storytelling power. Each verse offers a glimpse into the wanderer’s life, filled with challenges and triumphs. The chorus, resonating with determination, embodies the heart of the outlaw country movement and its enduring appeal.
15. “L.A. Freeway” – Guy Clark (1975)
“L.A. Freeway” by Guy Clark is a poetic masterpiece from 1975 that speaks to the desire for freedom and authenticity. Clark’s storytelling is vivid, painting a picture of escape from the city’s confines in search of something real. His vocals, heartfelt and genuine, resonate with those yearning for a simpler life. The song’s melody, gentle yet powerful, underscores the narrative’s emotional weight. In the chorus, Clark’s voice evokes a sense of hope and determination, capturing the listener’s imagination. It’s a timeless track that continues to inspire those seeking to break free from life’s constraints.
16. “Misery and Gin” – Merle Haggard (1980)
Merle Haggard’s “Misery and Gin” from 1980 is a poignant exploration of heartache and resilience. Haggard’s voice, rich with emotion, draws listeners into a world of longing and reflection. The song’s melody, both haunting and comforting, complements the lyrical depth. Each verse unfolds with honesty, revealing the struggles and triumphs of life. In the chorus, Haggard’s vocals resonate with a sense of acceptance and understanding, offering solace to those who listen. The simplicity of the arrangement allows the song’s message to shine, creating a powerful connection with the audience. It’s a timeless classic that continues to resonate.
17. “Whiskey River” – Johnny Bush (1972)
Johnny Bush’s “Whiskey River” from 1972 is an energetic anthem that later became famous through Willie Nelson’s rendition. Bush’s version, however, possesses a raw energy and authenticity that captivates listeners. His commanding vocals and dynamic instrumentation create a lively sound that draws listeners in. The song’s melody is infectious, with a rhythm that compels movement and engagement. Each verse unfolds with enthusiasm, celebrating life’s ups and downs. In the chorus, Bush’s voice resonates with passion, embodying the spirit of the outlaw country movement. It’s a track that demands attention, leaving a lasting impression on all who hear it.
18. “Trudy” – Charlie Daniels (1974)
Charlie Daniels’ “Trudy” from 1974 is a groovy, swampy tune that blends outlaw country with blues influences. Daniels’ energetic performance and skillful musicianship bring the song to life, creating a captivating experience. His vibrant vocals, paired with dynamic instrumentation, offer a rich tapestry of sound that draws listeners in. The song’s melody is infectious, with a rhythm that invites movement and engagement. In the verses, Daniels weaves a narrative filled with intrigue and adventure, captivating the audience’s imagination. The chorus, lively and engaging, embodies the spirit of the outlaw movement, making it a standout track in his discography.
19. “Women Do Know How to Carry On” – Waylon Jennings (1982)
Waylon Jennings’ “Women Do Know How to Carry On” from 1982 is a hidden gem that balances grit with tenderness. Jennings’ vocals, both powerful and soothing, deliver a message of resilience and strength. The song’s melody, a blend of traditional country elements and modern influences, creates a captivating soundscape. Each verse unfolds with grace, offering insights into the complexities of love and life. In the chorus, Jennings’ voice resonates with sincerity, embodying the song’s heartfelt message. It’s a testament to his ability to craft songs that resonate deeply, leaving a lasting impact on listeners.
20. “Rough and Rowdy Days” – Waylon Jennings (1998)
Waylon Jennings’ “Rough and Rowdy Days” from 1998 is a testament to his enduring outlaw spirit. Despite being a late-career track, it captures the essence of Jennings’ rebellious ethos. His vocals, seasoned and powerful, convey a sense of wisdom and reflection. The song’s melody, both dynamic and introspective, underscores the narrative’s emotional depth. Each verse tells a story of a life lived fully, filled with challenges and triumphs. In the chorus, Jennings’ voice resonates with determination, embodying the spirit of the outlaw movement. It’s a fitting tribute to his legacy, celebrating a life of authenticity and resilience.