Waylon Jennings was an influential American country music singer, songwriter, and musician, often credited with helping to popularize the outlaw country movement. Born on June 15, 1937, in Littlefield, Texas, Jennings began his career as a disc jockey and performer, eventually joining Buddy Holly’s band, The Crickets, shortly before Holly’s tragic plane crash. Jennings’s career took off in the 1970s with hits like “Good Hearted Woman,” “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” and “Luckenbach, Texas (Back to the Basics of Love).” Known for his deep, resonant voice and rebellious image, Jennings pushed against the Nashville establishment, favoring a rawer, more authentic sound. His collaborations with fellow outlaws like Willie Nelson and Johnny Cash further solidified his legacy as a country music icon.
1. Good Hearted Woman
“Good Hearted Woman” is a classic country song by Waylon Jennings, co-written with Willie Nelson. Released in 1972 on Jennings’ album of the same name, the song became one of his signature hits. It tells the story of a devoted woman who loves a wayward man despite his flaws and wild lifestyle. The song blends traditional country music with the outlaw country movement’s rebellious spirit, featuring Jennings’ rich baritone voice and a distinctive honky-tonk rhythm. “Good Hearted Woman” exemplifies Jennings’ ability to convey deep emotion and real-life storytelling, making it a timeless piece in country music history.
2. Luckenbach, Texas (Back to the Basics of Love)
“Luckenbach, Texas (Back to the Basics of Love)” is a renowned country song by Waylon Jennings, featuring Willie Nelson. Released in 1977 as part of Jennings’ album “Ol’ Waylon,” the song became a major hit and a defining anthem of the outlaw country movement. Written by Bobby Emmons and Chips Moman, the lyrics nostalgically evoke a simpler, more authentic way of life, urging a return to the basics of love and contentment away from materialism and societal pressures. Set against the backdrop of the small town of Luckenbach, Texas, the song features Jennings’ smooth vocals and a laid-back, acoustic-driven melody, capturing the essence of traditional country music and the desire for a return to roots.
3. Mammas Don’t Let Your Babies Grow Up to Be Cowboys
“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” is a classic country song popularized by Waylon Jennings and Willie Nelson. Originally written by Ed Bruce and Patsy Bruce, it was first recorded by Ed Bruce in 1975. The Jennings and Nelson version, released in 1978 on their duet album “Waylon & Willie,” became a major hit. The song advises mothers to steer their children away from the hard and lonely life of a cowboy, highlighting the difficulties and uncertainties of the lifestyle. With its memorable chorus, heartfelt lyrics, and the distinctive voices of Jennings and Nelson, the song encapsulates the spirit of the outlaw country genre and remains an enduring favorite in country music.
4. I’m a Ramblin’ Man
“I’m a Ramblin’ Man” is a hit song by Waylon Jennings, released in 1974 on his album *The Ramblin’ Man*. Written by Ray Pennington, the song features Jennings’s signature blend of honky-tonk and outlaw country styles. The lyrics tell the story of a restless man who is always on the move, warning potential lovers of his inability to settle down. The song’s upbeat tempo, driving rhythm, and Jennings’s distinctive voice contributed to its success, reaching number one on the Billboard Hot Country Singles chart. “I’m a Ramblin’ Man” remains one of Jennings’s most well-known and beloved tracks, epitomizing his image as a country music rebel.
5. Are You Sure Hank Done It This Way
“Are You Sure Hank Done It This Way” is a classic song by Waylon Jennings, released in 1975 as part of his album *Dreaming My Dreams*. The song, written by Jennings himself, reflects on the changes in the country music industry and pays homage to Hank Williams, one of country music’s greatest legends. With its straightforward lyrics and Jennings’s rugged vocal delivery, the song critiques the commercialization of the genre and questions whether modern practices align with the authentic spirit of traditional country music exemplified by Hank Williams. The track became a hit, reaching number one on the Billboard Hot Country Singles chart, and is celebrated for its introspective look at the music industry and its tribute to Hank Williams’s enduring influence.
6. I’ve Always Been Crazy
“I’ve Always Been Crazy” is a classic country song by Waylon Jennings, released in 1978 as the title track of his album. Written by Jennings himself, the song reflects his rebellious persona and free-spirited attitude towards life. It’s an anthem of self-acceptance and defiance against societal norms, celebrating individuality and personal freedom. Musically, the song blends traditional country elements with Jennings’ distinctive voice and rock-inspired instrumentation, showcasing his unique blend of outlaw country and honky-tonk styles. “I’ve Always Been Crazy” became one of Jennings’ signature songs, resonating with fans who appreciated its honesty, authenticity, and unapologetic approach to life.
7. Don’t You Think This Outlaw Bit’s Done Got Out of Hand
“Don’t You Think This Outlaw Bit’s Done Got Out of Hand” is a poignant country song by Waylon Jennings, released in 1978 as a single from his album of the same name. Written by Billy Joe Shaver, the song reflects on the consequences and complexities of the outlaw country movement that Jennings and others were part of. It explores themes of fame, rebellion, and the struggles of staying true to oneself amidst changing times. Musically, the song features Jennings’ deep, soulful vocals and a blend of traditional country and rock influences, characteristic of his outlaw country style. It remains a significant piece in Jennings’ discography, showcasing his introspective songwriting and powerful storytelling.
8. Honky Tonk Heroes
*Honky Tonk Heroes* is a seminal album by Waylon Jennings, released in 1973. Widely regarded as a cornerstone of the outlaw country movement, the album features songs primarily written by Billy Joe Shaver, whose raw, authentic songwriting resonated with Jennings’s own rebellious spirit. The title track, “Honky Tonk Heroes,” sets the tone with its gritty depiction of barroom life and hard-living characters. The album’s blend of honky-tonk, rock, and traditional country elements marked a departure from the polished Nashville sound, emphasizing a more stripped-down and genuine approach. *Honky Tonk Heroes* solidified Jennings’s reputation as a leading figure in the outlaw country genre and remains a landmark in country music history.
9. Only Daddy That’ll Walk the Line
“Only Daddy That’ll Walk the Line” is a classic country song performed by Waylon Jennings. Released in 1968, it became one of his early hits and a signature song in his career. Written by Ivy J. Bryant, the song features a strong, assertive vocal delivery from Jennings and a distinctive blend of country and rockabilly influences. The lyrics convey a sense of independence and nonconformity, with Jennings portraying a man who lives life on his own terms, unwilling to settle down or conform to societal expectations. “Only Daddy That’ll Walk the Line” solidified Jennings’ reputation as a pioneering figure in the outlaw country movement, known for his gritty, rebellious style and distinctive voice.
10. Amanda
“Amanda” is a heartfelt country ballad originally written and recorded by Bob McDill in 1973. It gained widespread popularity when Waylon Jennings released his version in 1979 on the album “Greatest Hits.” The song tells the story of a man reflecting on his deep love for a woman named Amanda, expressing regret over past mistakes and longing for reconciliation. With its tender melody and emotional lyrics, “Amanda” became a major hit for Jennings, reaching the top of the country charts and becoming one of his most iconic songs. It showcases Jennings’ ability to convey raw emotion and sincerity through his rich baritone voice.