Waylon Jennings, born on June 15, 1937, in Littlefield, Texas, was an American country music icon known for his rebellious spirit and distinctive outlaw country sound. Emerging in the 1960s, Jennings defied Nashville conventions, opting for a raw and gritty style that set him apart from the polished mainstream. His deep, resonant voice and honky-tonk influences made him a pivotal figure in shaping the outlaw country movement.
Jennings gained widespread recognition for his association with the supergroup The Highwaymen, alongside Johnny Cash, Willie Nelson, and Kris Kristofferson. His remarkable discography includes hits like “Good Hearted Woman,” “Mamas Don’t Let Your Babies Grow Up to Be Cowboys,” and the anthemic “Are You Sure Hank Done It This Way.”
His rebellious image extended beyond his music, as he famously gave up his seat on the ill-fated flight that later claimed the lives of Buddy Holly, Ritchie Valens, and J.P. Richardson. This fateful decision haunted Jennings throughout his life.
Waylon Jennings left an indelible mark on country music, earning him accolades, including multiple Grammy Awards. His legacy endures not only through his chart-topping hits but also as a symbol of authenticity and independence in the world of country music. Jennings passed away on February 13, 2002, but his impact on the genre and his status as an outlaw country pioneer continue to resonate with fans and musicians alike.
1. Luckenbach, Texas (Back to the Basics of Love)
“Luckenbach, Texas (Back to the Basics of Love)” is a classic country song performed by Waylon Jennings. Co-written by Bobby Emmons and Chips Moman, the song was released in 1977 as the title track of Jennings’ album “Ol’ Waylon.” The track, infused with Waylon’s distinctive outlaw country sound, became one of his signature songs.
The lyrics of “Luckenbach, Texas” depict a desire to escape the trappings of modern life and find solace in a simpler, more genuine existence. The reference to Luckenbach, a small Texas town, serves as a metaphor for a place where people can rediscover the fundamentals of love and happiness, away from the complexities of contemporary living.
The song’s catchy melody, Waylon Jennings’ laid-back yet authoritative vocals, and the prominent steel guitar contribute to its timeless appeal. “Luckenbach, Texas” became a major hit, reaching the top of the country charts and solidifying Waylon Jennings’ status as a leading figure in the outlaw country movement.
Decades after its release, “Luckenbach, Texas” remains a beloved country classic, celebrated for its authenticity, its nod to a simpler way of life, and its enduring contribution to the legacy of Waylon Jennings and outlaw country music.
2. 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 recorded by Waylon Jennings and Willie Nelson. The song was written by Ed Bruce and Patsy Bruce and was released in 1978 as a single. It became a hit and won the Grammy Award for Best Country Performance by a Duo or Group with Vocal.
The lyrics offer advice to mothers, suggesting that they shouldn’t let their children grow up to be cowboys. The song portrays the challenges and hardships of the cowboy lifestyle, emphasizing the tough and often unpredictable nature of the profession.
The collaboration between Waylon Jennings and Willie Nelson on this track showcased the chemistry between the two outlaw country icons. Their contrasting yet complementary voices and the authenticity they brought to the performance contributed to the success of the song.
“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” became a country music anthem and is considered one of the definitive songs in the outlaw country subgenre. The song’s popularity endured over the years, and it remains a cherished classic in the country music canon, celebrated for its memorable lyrics, heartfelt delivery, and the collaboration of two legendary artists.
3. Good Hearted Woman
“Good Hearted Woman” is a classic country song written by Waylon Jennings and Willie Nelson. It was originally released as a single by Jennings in 1972 and later appeared on the album of the same name, which was a collaborative effort by Jennings and Nelson.
The song tells the story of a man who appreciates and values the qualities of a “good-hearted woman” in his life. It explores themes of love, loyalty, and the importance of having a supportive partner. The lyrics convey a deep sense of gratitude for the woman’s positive qualities and understanding nature.
Jennings and Nelson’s collaboration on “Good Hearted Woman” became one of the defining moments in outlaw country music. The song’s laid-back and honky-tonk style, coupled with the distinctive voices of both artists, contributed to its success. The catchy chorus and memorable lyrics made it a favorite among country music fans.
“Good Hearted Woman” has endured as a country music classic and has been covered by various artists over the years. The song’s legacy lies not only in its musical appeal but also in its representation of the outlaw country movement, which rebelled against the Nashville establishment and embraced a more raw and authentic approach to country music.
4. Are You Sure Hank Done It This Way
“Are You Sure Hank Done It This Way” is a classic country song written and performed by Waylon Jennings. It was released in 1975 as the first single from his album “Dreaming My Dreams.” The song reflects Jennings’ rebellious attitude and his critiques of the changing landscape of country music during the 1970s.
In “Are You Sure Hank Done It This Way,” Jennings expresses concern about the direction country music was heading and laments the loss of its traditional roots. The lyrics question whether Hank Williams, one of the genre’s pioneers, would have embraced the changing trends. It addresses the commercialization of country music and the shift away from the honky-tonk and outlaw sounds that were characteristic of earlier decades.
Jennings’ delivery, marked by his distinctive voice and assertive style, captures the essence of the outlaw country movement. The song became a hit and is often regarded as one of Waylon Jennings’ signature tracks. Its impact goes beyond its success on the charts, as it became an anthem for those who appreciated the raw, unvarnished style of country music that characterized the outlaw movement.
5. I’ve Always Been Crazy
“I’ve Always Been Crazy” is a song by Waylon Jennings, released in 1978 as the title track of his album of the same name. The song was written by Waylon Jennings himself and reflects his rebellious, free-spirited nature.
The lyrics convey Jennings’ unapologetic attitude and his refusal to conform to societal norms. The chorus declares, “I’ve always been crazy, but it’s kept me from going insane,” expressing a sense of self-awareness and embracing one’s individuality.
The song features a country-rock sound, showcasing Jennings’ distinct vocal delivery and his signature blend of traditional country elements with a more contemporary edge. The upbeat tempo and energetic instrumentation contribute to the song’s lively and rebellious spirit.
“I’ve Always Been Crazy” became one of Waylon Jennings’ notable hits, reaching high positions on the country charts. The song is often celebrated for its candid lyrics, which resonate with those who appreciate Jennings’ outlaw country persona. The title track, along with the entire album, further solidified Jennings’ status as a pioneer of the outlaw country movement in the 1970s.
6. Amanda
“Amanda” is a power ballad by the rock band Boston, written by band member Tom Scholz. It was released as a single from their third studio album, “Third Stage,” in 1986. The song is known for its emotional lyrics and melodic composition.
“Amanda” became Boston’s most successful single, reaching the top of the Billboard Hot 100 chart. The song’s success was not only attributed to its catchy melody and heartfelt lyrics but also to its timing, as it became a popular slow dance and wedding song.
The lyrics of “Amanda” express themes of love and longing, with the narrator professing deep emotions for the titular character. The chorus features the memorable refrain “Amanda, light of my life, fate should have made you a gentleman’s wife.”
Tom Scholz, known for his meticulous approach to production, created a polished and radio-friendly sound for “Amanda,” contributing to its widespread appeal. The song remains a classic representation of 1980s rock ballads and is a significant part of Boston’s musical legacy.
7. I Ain’t Living Long Like This
“I Ain’t Living Long Like This” is a country song written by Rodney Crowell. It was first recorded by Emmylou Harris for her 1978 album of the same name. However, the song gained significant attention and commercial success when Waylon Jennings recorded and released his version as the title track of his 1979 album.
Waylon Jennings’ rendition of “I Ain’t Living Long Like This” showcases his signature outlaw country sound with a gritty and rebellious edge. The song’s lyrics convey a sense of restlessness and a refusal to conform to societal norms. It became a hit for Jennings, reaching the top of the country charts.
The track has been covered by various artists over the years, reflecting its enduring appeal within the country music genre. Notably, the song has been performed by artists such as Dwight Yoakam and Chris LeDoux, contributing to its status as a classic in outlaw country music.
“I Ain’t Living Long Like This” remains a standout track in Waylon Jennings’ catalog and is celebrated for its gritty sound, rebellious spirit, and its representation of the outlaw movement within country music during the late 1970s.
8. The Wurlitzer Prize (I Don’t Want to Get Over You)
“The Wurlitzer Prize (I Don’t Want to Get Over You)” is a country song performed by Waylon Jennings. Released in 1977 as a single from his album “Ol’ Waylon,” the song is a heartfelt ballad written by Chips Moman and Bobby Emmons.
The lyrics of “The Wurlitzer Prize” convey the emotional struggle of a man who, despite his best efforts, cannot move on from a past love. The Wurlitzer Prize mentioned in the title refers to a jukebox, symbolizing the sentimental power of music and how it can evoke memories and emotions.
Waylon Jennings’ soulful and resonant delivery adds depth to the song, capturing the bittersweet essence of heartbreak and unrequited love. The combination of the evocative lyrics and Jennings’ distinctive vocal style contributes to the enduring appeal of the track.
While not as commercially successful as some of Jennings’ other hits, “The Wurlitzer Prize” has become a favorite among country music enthusiasts. Its poignant portrayal of the lingering pain of lost love and the solace sought through music showcases Jennings’ ability to convey deep emotions through his music.
9. Only Daddy That’ll Walk the Line
“Only Daddy That’ll Walk the Line” is a classic country song written and originally recorded by Waylon Jennings. It was released as a single in 1968 and became one of Jennings’ early hits, marking a significant moment in the development of his outlaw country sound.
The song is characterized by a twangy guitar riff and Jennings’ distinctive vocal delivery. Lyrically, “Only Daddy That’ll Walk the Line” explores themes of independence and nonconformity, with the narrator expressing a willingness to stand out and live life on his own terms. The title phrase suggests a sense of uniqueness and individuality.
Jennings’ version of the song achieved success on the country charts, and it is often considered one of his signature tracks. The song’s raw and rebellious energy contributed to the emerging outlaw country movement, challenging the polished and orchestrated Nashville sound prevalent at the time.
“Only Daddy That’ll Walk the Line” remains a classic example of Waylon Jennings’ influential contribution to country music, showcasing his distinctive style and paving the way for the outlaw country movement that would gain prominence in the 1970s.
10. Just to Satisfy You
“Just to Satisfy You” is a country song performed by Waylon Jennings and Willie Nelson. It was written by Jennings and Don Bowman and was released in 1969 as a single. The song was included on the album of the same name, which featured the collaborative efforts of the two outlaw country legends.
The lyrics of “Just to Satisfy You” explore the theme of a complicated relationship, expressing a willingness to go to great lengths just to please the other person. The narrative touches upon the challenges and sacrifices inherent in romantic relationships.
The chemistry between Waylon Jennings and Willie Nelson shines through in their vocal harmonies and the authenticity they bring to the song. Their partnership was known for blending their distinct voices and styles, creating a unique sound that became a hallmark of outlaw country.
“Just to Satisfy You” achieved success on the country charts, reaching high positions. The song’s enduring popularity is a testament to the musical camaraderie between Jennings and Nelson and their ability to convey the complexities of love through their collaborative efforts.
Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
