Waylon Jennings (1937-2002) was an influential American country music singer, songwriter, and musician. Born on June 15, 1937, in Littlefield, Texas, Jennings played a crucial role in the Outlaw Country movement, challenging the conventions of the Nashville sound and reshaping the landscape of country music.
Jennings began his musical career as a radio DJ and played bass guitar for Buddy Holly during the late 1950s. After Holly’s tragic death in 1959, Jennings became a prominent figure in the country music scene. He signed with RCA Records in the 1960s and released a series of successful albums.
In the early 1970s, Jennings, along with Willie Nelson, Tompall Glaser, and others, helped pioneer the Outlaw Country movement, which sought to move away from the polished Nashville sound and embrace a more rebellious, authentic approach to country music. Jennings’s album “Honky Tonk Heroes” (1973) is often considered a landmark in the Outlaw Country genre.
Some of Waylon Jennings’s most well-known songs include “Good Hearted Woman,” “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (with Willie Nelson), “Are You Sure Hank Done It This Way,” and “Luckenbach, Texas (Back to the Basics of Love).” His deep, resonant voice and distinctive style made him a beloved figure in country music.
Waylon Jennings continued to enjoy success throughout his career and received numerous awards, including Grammy Awards and the Country Music Association Awards. He passed away on February 13, 2002, leaving a lasting legacy as one of the key figures in the evolution of country music.
1. “Good Hearted Woman”
“Good Hearted Woman” is a classic country song performed by Waylon Jennings. Co-written by Jennings and Willie Nelson, the song was first released in 1972 as the title track of Jennings’ album “Good Hearted Woman.”
The lyrics tell the story of a man who appreciates and cherishes the qualities of a “good-hearted woman” despite the challenges and hardships he may face. The song reflects a genuine and enduring love, celebrating the virtues of loyalty and commitment.
In 1976, Jennings and Willie Nelson recorded a new version of “Good Hearted Woman” as a duet, which became the title track of their collaborative album. This version was released as a single and became a major hit, reaching the top of the country charts. The success of the song further solidified the partnership between Jennings and Nelson and their impact on the Outlaw Country movement.
“Good Hearted Woman” has remained one of Waylon Jennings’ signature songs, praised for its heartfelt lyrics, Jennings’ distinctive voice, and the enduring appeal of its classic country sound. The song continues to be celebrated as a defining example of the Outlaw Country genre.
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 country song written by Ed Bruce and Patsy Bruce. It was first recorded by Ed Bruce and his wife Patsy Bruce for Ed Bruce’s 1976 self-titled album. However, the song gained widespread recognition when it was covered by Willie Nelson and Waylon Jennings as a duet.
Nelson and Jennings recorded their version of the song for their duet album “Waylon & Willie,” released in 1978. The album became a major success, and “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” was one of its standout tracks. The song won the Grammy Award for Best Country Performance by a Duo or Group with Vocal in 1979.
The lyrics of the song humorously advise mothers not to let their children become cowboys, as it’s a tough and rugged life. Despite the warning, the song celebrates the cowboy spirit and the freedom associated with that lifestyle.
The duet between Willie Nelson and Waylon Jennings, two iconic figures in country music, added to the song’s appeal, and it became a country classic. The track is known for its catchy melody, straightforward lyrics, and the chemistry between Nelson and Jennings in their vocal delivery.
3. “Luckenbach, Texas (Back to the Basics of Love)”
“Luckenbach, Texas (Back to the Basics of Love)” is a country song performed by Waylon Jennings. It was written by Bobby Emmons and Chips Moman and was released in 1977 as the title track of Jennings’ album “Ol’ Waylon.” The song became one of Waylon Jennings’ signature hits and is considered a classic in the country music genre.
The lyrics of “Luckenbach, Texas” humorously reference the small town of Luckenbach as a place where people can go to get away from the pressures of modern life and find simplicity and love. The song suggests that sometimes returning to the basics of love and relationships is the key to happiness.
The chorus famously mentions:
“Let’s go to Luckenbach, Texas
With Waylon and Willie and the boys
This successful life we’re livin’
Got us feudin’ like the Hatfields and McCoys.”
The mention of “Waylon and Willie and the boys” refers to Waylon Jennings and Willie Nelson, two influential figures in outlaw country music, who collaborated on various projects.
“Luckenbach, Texas” became a chart-topping hit, reaching No. 1 on the Billboard Hot Country Singles chart. The song’s popularity has endured over the years, and it remains a beloved and often-covered classic in the country music canon.
4. “Amanda”
“Amanda” is a country song written by Bob McDill and popularized by Waylon Jennings. It was released as a single in 1979 and became one of Jennings’ most successful and well-known songs. The song was included on his album “Greatest Hits.”
The lyrics of “Amanda” tell the story of a man expressing his love and devotion to a woman named Amanda. The song captures the emotions of longing and the deep connection between two people. The narrator reflects on the impact Amanda has had on his life and expresses a sense of gratitude and appreciation for her presence.
“Amanda” reached No. 1 on the Billboard Hot Country Singles chart in 1979, becoming Waylon Jennings’ eighth No. 1 hit on the country charts. The song’s success helped it cross over to the pop charts, making it one of his most commercially successful songs.
Jennings’ heartfelt delivery and the timeless appeal of the song’s theme have made “Amanda” a classic in the country music genre. The song remains a fan favorite and is often remembered as one of Waylon Jennings’ signature hits.
5. “Are You Sure Hank Done It This Way”
“Are You Sure Hank Done It This Way” is a song by American country music artist Waylon Jennings. It was written by Jennings and released as a single in 1975. The song appears on his album “Dreaming My Dreams.”
The lyrics of the song reflect on the changing landscape of country music and the evolving trends in the industry during the 1970s. Waylon Jennings, known for his outlaw country style, questions the direction of the genre and whether it has strayed from the traditional sound and values associated with country music.
The title of the song references Hank Williams, one of the most influential figures in the history of country music. Jennings contemplates whether Hank Williams, if he were alive, would approve of the contemporary developments in the genre.
“Are You Sure Hank Done It This Way” became one of Waylon Jennings’ notable hits and is often cited as a representative song of the outlaw country movement. The track showcases Jennings’ distinctive vocal style and his willingness to challenge established norms within the country music industry.
6. “I’m a Ramblin’ Man”
“I’m a Ramblin’ Man” is a classic country song performed by Waylon Jennings. Written by Ray Pennington, the song was released as a single in 1974 and became one of Jennings’ signature hits. It was included on his album of the same name.
The lyrics of “I’m a Ramblin’ Man” reflect the life of a free-spirited and nomadic individual who prefers a life on the road, moving from place to place. The narrator acknowledges his wandering nature and the challenges it presents in forming lasting relationships, but he expresses a commitment to remaining true to his own way of life.
The song became a major success for Waylon Jennings, reaching No. 1 on the Billboard Hot Country Singles chart in 1974. “I’m a Ramblin’ Man” is often cited as one of the defining tracks of the Outlaw Country movement, with Jennings’ distinctive voice and the song’s lively, honky-tonk sound contributing to its popularity.
The timeless theme of a free-spirited wanderer resonated with country music audiences, and the song remains a classic in Waylon Jennings’ discography, showcasing his outlaw image and musical style.
7. “Honky Tonk Heroes”
“Honky Tonk Heroes” is a song written by Billy Joe Shaver, and it became the title track of Waylon Jennings’ 1973 album. The album, “Honky Tonk Heroes,” is considered a landmark in the outlaw country music movement and features Shaver’s songs performed by Jennings.
The lyrics of “Honky Tonk Heroes” celebrate the gritty and rebellious spirit of the honky-tonk lifestyle. The song pays homage to those who live on the fringes of society, finding solace and identity in honky-tonk bars. Shaver’s lyrics resonate with themes of resilience, survival, and the authenticity of the honky-tonk experience.
Waylon Jennings’ rendition of “Honky Tonk Heroes” is widely praised for its raw and unpolished sound, reflecting the outlaw country ethos. The album marked a departure from the polished Nashville sound, embracing a more rugged and individualistic approach to country music production.
The song “Honky Tonk Heroes” and the album of the same name played a pivotal role in defining the outlaw country movement. It showcased a departure from the conventions of mainstream country music and emphasized a more rebellious and authentic approach. The album is often regarded as a classic in the outlaw country genre.
8. “Lonesome, On’ry and Mean”
“Lonesome, On’ry and Mean” is a song by Waylon Jennings, released in 1973 as the title track of his album of the same name. The song was written by Steve Young and reflects the Outlaw Country sound that Jennings helped popularize during the 1970s.
The lyrics of “Lonesome, On’ry and Mean” capture the essence of a rebel, an individual who is solitary, tough, and not easily swayed by societal norms. The term “lonesome, on’ry, and mean” describes the narrator’s rugged and independent nature, emphasizing his resilience and refusal to conform.
The song became one of Waylon Jennings’ notable hits and is often regarded as a quintessential example of Outlaw Country music. It resonated with audiences who appreciated the authenticity and rebellious spirit conveyed in the lyrics and the performance.
“Lonesome, On’ry and Mean” is considered an important contribution to the Outlaw Country movement, and it remains a well-loved and enduring track in Waylon Jennings’ catalog. The song’s impact extends beyond its initial release, as it continues to be celebrated by fans of classic country and Outlaw Country music.
9. “Rainy Day Woman”
“Rainy Day Woman” is a country song by Waylon Jennings, released in 1974 as part of his album “This Time.” The song explores themes of heartache and the emotional impact of a failed relationship.
The lyrics of “Rainy Day Woman” depict a narrator who is heartbroken and unable to move on from a lost love. The rainy day serves as a metaphor for the emotional turmoil and sadness he feels. Waylon Jennings’ soulful vocals capture the depth of emotion in the song.
Musically, the song features a melancholic and introspective sound, with acoustic guitar and emotional steel guitar solos. The song’s arrangement creates a somber atmosphere that complements the lyrics.
“Rainy Day Woman” is a poignant country ballad that resonates with anyone who has experienced the pain of heartbreak. Waylon Jennings’ emotive delivery and the song’s relatable themes have made it a timeless addition to his catalog.
10. “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 and captures the Outlaw Country sound for which he became known during the 1970s.
The lyrics of “I’ve Always Been Crazy” reflect Jennings’ rebellious and independent spirit. The narrator acknowledges his unconventional lifestyle, embracing his wild and free nature. The chorus features the memorable line “I’ve always been crazy, but it’s kept me from going insane,” expressing a sense of self-awareness and acceptance.
The song became a hit for Waylon Jennings, reaching the top of the Billboard Hot Country Singles chart in 1978. Its success further solidified Jennings’ reputation as a leading figure in the Outlaw Country movement. The accompanying album, “I’ve Always Been Crazy,” continued to showcase Jennings’ unique blend of country, rock, and outlaw sensibilities.
“I’ve Always Been Crazy” remains one of Waylon Jennings’ signature songs and is celebrated for its energetic performance, straightforward lyrics, and the defiant attitude that defined the Outlaw Country genre.
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.
