Renowned country music icon Waylon Jennings passed away on February 12, 2002, but his profound influence on the genre will forever remain. Not only did Jennings achieve numerous chart-topping hits as a solo artist, but he also found great success as a member of the esteemed supergroup, the Highwaymen, alongside fellow legends Willie Nelson, Kris Kristofferson, and Johnny Cash.
During his remarkable journey in the music industry, Jennings released an impressive catalogue of over 80 albums and had more than 60 singles make their way onto the charts. Now, let’s delve into The CountryMusiX‘s selection of 10 of Jennings’ finest musical gems, each representing a pinnacle in his illustrious career.
10. “Rose in Paradise,”
“Rose in Paradise,” released in 1987 as the lead single from Jennings’ album “Hangin’ Tough,” holds a special place in his discography. Penned by Jim McBride and Stewart Harris, this captivating song tells the tale of a woman named Rose, who allegedly had a dark history of losing all five of her husbands under mysterious circumstances during the 1800s.
The inspiration for the song came from McBride’s personal encounter with the intriguing story of Rose. He recounts a house located outside of Huntsville, Alabama, where this enigmatic figure once resided. McBride shares, “She had five husbands who were all financially well-off, and each one of them met an untimely demise. Despite being taken to trial, Rose managed to escape any charges of poisoning her spouses, and the truth remained elusive.”
“Rose in Paradise” stands as a significant milestone in Jennings’ career, as it marked his twelfth and final No. 1 hit on the charts. With its mesmerizing storytelling and haunting melodies, the song encapsulates the essence of Jennings’ remarkable musical journey.
09. “Are You Sure Hank Done It This Way?”
“Are You Sure Hank Done It This Way?” is a captivating track featured on Jennings’ album “Dreaming My Dreams,” released in 1975. With this song, Jennings pays homage to the legendary Hank Williams while also raising thought-provoking questions about the direction of country music.
The lyrics of the song express Jennings’ contemplation on the state of the genre, challenging its conventional path. Lines like “Lord it’s the same old tune, fiddle and guitar” and “Where do we take it from here?” shed light on his desire for change and innovation within country music. The song addresses the prevalence of rhinestone suits and flashy cars, suggesting that the industry has remained stagnant for far too long.
With its heartfelt message and powerful delivery, “Are You Sure Hank Done It This Way?” became a chart-topping hit. The song’s impact extends beyond Jennings’ rendition, as it has been covered by notable artists such as Clint Black, Robert Earl Keen, Jack Ingram, and many others. Its enduring popularity is a testament to the timeless appeal of Jennings’ music and the universal resonance of his message.
“Highwayman” holds a significant place in the discography of the iconic quartet known as the Highwaymen. Released in 1985, it served as their debut single and the only one to achieve chart-topping success. The song, written by the talented Jimmy Webb, initially found its way into the music world through renditions by Webb himself and the renowned Glen Campbell. However, it was Marty Stuart’s persuasion that convinced the Highwaymen to record their own version of this timeless track.
“Highwayman” embodies the spirit of adventure and the allure of the open road. It tells the captivating tale of a reincarnating soul that traverses through different time periods and identities, experiencing various historical events and challenges. The song’s powerful narrative resonates with listeners, taking them on an imaginative journey through history and the mysteries of existence.
With its captivating storytelling and the collective talents of Waylon Jennings, Willie Nelson, Kris Kristofferson, and Johnny Cash, the Highwaymen’s rendition of “Highwayman” struck a chord with audiences worldwide. It swiftly climbed to the top of the charts, solidifying its place as a beloved classic.
The song’s enduring popularity and the group’s distinctive harmonies have made “Highwayman” an iconic anthem that continues to captivate listeners, reminding us of the timeless allure of the highway and the timeless talent of the Highwaymen.
07. “Luckenbach, Texas (Back to the Basics of Love)”
“Luckenbach, Texas (Back to the Basics of Love)” is an iconic track from Jennings’ album “Ol’ Waylon,” released in 1977. This chart-topping hit holds a special place in Jennings’ illustrious career, spending an impressive six weeks at the top of the charts. It stands as one of his most successful songs to date.
The song’s narrative revolves around a wealthy couple whose abundance of money is creating a divide between them. With heartfelt lyrics, it explores the notion that material wealth does not always equate to happiness and fulfillment in relationships. In a clever twist, the song references not only Jennings himself but also pays homage to fellow music legends Willie Nelson, Hank Williams, and Jerry Jeff Walker.
“Luckenbach, Texas (Back to the Basics of Love)” captures the essence of Jennings’ musical style and storytelling prowess. Its relatable theme and catchy melodies resonated deeply with audiences, propelling it to great heights of success.
Decades after its release, the song continues to be celebrated for its timeless message and the soulful performances by Jennings and his fellow musicians. It serves as a reminder that love and genuine connections are the true foundations of happiness, taking us back to the core values that truly matter.
06. “I’ve Always Been Crazy”
“I’ve Always Been Crazy” serves as the title track of Jennings’ 25th studio album, released in 1978. This powerful song encompasses the essence of Jennings’ tumultuous life and the struggles he faced. With poignant lyrics such as “I’ve always been crazy and the trouble that it’s put me through,” the song reflects on his rebellious nature and the consequences he has endured.
The lyrics acknowledge the ups and downs of Jennings’ life, admitting to being caught in situations he both deserved and didn’t deserve. Despite his flaws, he emphasizes that he has never intentionally caused harm to others. It is a raw and honest statement of self-reflection and acceptance of his past actions.
Jennings wrote this song as a personal declaration, inspired by a particular incident involving yet another drug bust related to his long-standing battle with cocaine. The media frenzy that ensued during that time deeply affected him. He vividly described the overwhelming presence of reporters swarming around him, comparing it to sharks detecting blood in the water.
“I’ve Always Been Crazy” showcases Jennings’ ability to confront his inner demons through music, laying bare his vulnerabilities for all to see. It serves as a testament to his resilience and willingness to acknowledge his imperfections.
The song’s raw honesty and Jennings’ undeniable talent resonated with audiences, cementing its status as a fan favorite. It remains an iconic anthem that captures the spirit of self-reflection and personal growth in the face of adversity.
05. “Theme From ‘Dukes of Hazzard’ (Good Ol’ Boys)”
“Theme From ‘Dukes of Hazzard’ (Good Ol’ Boys)” was a significant contribution by Jennings to the immensely popular TV show, Dukes of Hazzard. Not only did he lend his powerful vocals to the theme song, but he also took on the role of the show’s narrator. However, it’s worth noting that there were slight variations between the TV and radio versions of the song.
In the TV version, the lyrics included the line “Fightin’ the system like two modern-day Robin Hoods,” which highlighted the show’s central theme of the Duke boys standing up against injustice. On the other hand, the radio version featured an additional line: “You know my momma loved me, but she don’t understand, they keep showing my hands and not my face on TV.” This line cleverly alluded to the producers’ tendency to focus on the actors’ hands during certain scenes, rather than showing their faces.
Jennings’ involvement in both the musical and narrative aspects of the show solidified his connection to the beloved Dukes of Hazzard series. His distinct voice and engaging storytelling made him an integral part of the show’s success.
“Theme From ‘Dukes of Hazzard’ (Good Ol’ Boys)” became synonymous with the adventurous spirit and rebellious charm of the Duke boys. The song’s catchy melodies and relatable lyrics resonated with audiences, propelling it to great popularity.
Decades later, the song continues to evoke nostalgia and fond memories for fans of the show. It remains an enduring anthem that represents the spirit of friendship, resilience, and standing up for what is right, just like the iconic characters of the Dukes of Hazzard.
04. “Good Hearted Woman”
“Good Hearted Woman” holds a special place as the title track of Jennings’ 16th studio album, released in 1972. This remarkable song came to life through a collaborative effort between Jennings and his dear friend Willie Nelson. The inspiration struck them while they were on the road together and encountered a sign advertising Ike and Tina Turner. The sign described Tina Turner as a “good-hearted woman loving two-timing men.” This intriguing phrase sparked their creative minds.
The two talented musicians found themselves engaged in a friendly game of poker when the lyrics began to flow. As Jennings and Nelson shared their thoughts and ideas, Nelson’s then-wife, Connie Koepke, skillfully transcribed the words, capturing the essence of their spontaneous creation.
“Good Hearted Woman” captures the essence of a resilient and compassionate woman who finds herself entangled in relationships with men who may not be entirely faithful. The song praises her loving nature and her ability to endure through challenging circumstances. Its heartfelt lyrics and infectious melody resonated with listeners, making it a memorable addition to Jennings’ repertoire.
The collaboration between Jennings and Nelson, two legendary figures in the world of country music, resulted in a timeless anthem that showcases their songwriting prowess and musical chemistry. “Good Hearted Woman” remains an enduring favorite, loved by fans for its relatable themes and captivating storytelling.
The song’s creation story adds a layer of intrigue, emphasizing the spontaneous and organic nature of its inception. It stands as a testament to the power of collaboration and the magic that can happen when talented artists come together to create something truly special.
03. “I’m a Ramblin’ Man”
“I’m a Ramblin’ Man” is a timeless track from Jennings’ album “The Ramblin’ Man,” released in 1974. The song’s original version was written and recorded by Ray Pennington, and Jennings was an admirer of Pennington’s rendition. Jennings had always promised to record his own version of “I’m a Ramblin’ Man,” but it wasn’t until Pennington wrote another song that caught Jennings’ attention that he fulfilled that promise.
Jennings expressed his admiration for Pennington’s record, stating, “I loved Ray’s version of it.” However, it was another song called “Oklahoma Sunshine” that truly captured Jennings’ interest. He made a deal with Pennington, proposing that if he could record “Oklahoma Sunshine,” he would also record “I’m a Ramblin’ Man” and let Pennington produce both tracks.
This agreement led to Jennings’ remarkable rendition of “I’m a Ramblin’ Man,” which resonated deeply with audiences. The song embodies the spirit of adventure and the restless nature of a wandering soul. Its catchy melodies and Jennings’ distinct vocals captured the essence of the rambling lifestyle, portraying the excitement and challenges that come with it.
The story behind the song’s production adds an intriguing layer to its legacy. The mutual admiration between Jennings and Pennington, along with their collaborative effort, resulted in a remarkable recording that showcases Jennings’ artistic integrity and Pennington’s production skills.
“I’m a Ramblin’ Man” remains a fan favorite, cherished for its spirited lyrics and captivating musical arrangement. It stands as a testament to Jennings’ ability to bring life to a song and make it his own while honoring the talent and contributions of fellow musicians.
“Amanda” holds a special place in Jennings’ discography as a timeless classic. The song, originally penned by Bob McDill, was first recorded by Don Williams. However, Jennings recognized the beauty and emotional depth of “Amanda” and decided to include his own rendition on his album “The Ramblin’ Man” in 1974. Interestingly, it wasn’t until his “Greatest Hits” album that he released “Amanda” as a single.
Upon its release, “Amanda” soared to the top of the charts, captivating listeners with its heartfelt lyrics and Jennings’ soulful delivery. The song’s popularity and universal appeal led to its nomination for both a CMA Award and an ACM Award in the coveted category of Single of the Year.
The enchanting tale of “Amanda” explores the complexities of love and the profound impact one person can have on another’s life. McDill’s masterful songwriting and Jennings’ powerful interpretation evoked a deep emotional connection with audiences, propelling it to the pinnacle of success.
The inclusion of “Amanda” on Jennings’ “Greatest Hits” album solidified its status as an enduring favorite among fans. Its recognition and accolades further validate its significance in the country music landscape.
Decades later, “Amanda” continues to resonate with listeners, reminding us of the timeless power of love and the profound influence it can have on our lives. Jennings’ rendition of this heartfelt ballad remains a testament to his musical prowess and ability to evoke genuine emotions through his performances.
01. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys”
“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” is an iconic song that showcases the collaboration between Jennings and Nelson on their album “Waylon & Willie” released in 1978. The heartfelt lyrics were crafted by talented songwriting duo Ed and Patsy Bruce, who skillfully captured the essence of a mother’s plea.
Within the song, Jennings and Nelson deliver powerful lines that resonate with both parents and listeners alike. The lyrics advise, “Mamas, don’t let your babies grow up to be cowboys / Don’t let ’em pick guitars or drive them old trucks / Let ’em be doctors and lawyers and such.” The words convey a desire for children to pursue professions that provide stability and security.
Originally, Jennings recorded the song as a solo track, but he later realized the potential for something even greater. With the belief that the song would truly shine as a duet, Jennings invited Nelson to join him in bringing “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” to life. This decision proved to be a stroke of genius, as their combined voices and chemistry elevated the song to new heights.
The remarkable duet captured the hearts of listeners and stayed at the coveted No. 1 spot on the charts for an impressive four weeks. Its success not only propelled the song to new heights but also contributed to the overall triumph of the “Waylon & Willie” album, which held the top position for an impressive 10 weeks.
“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” resonates with audiences because it touches on the universal theme of parental concern and the desire to guide children towards a stable and fulfilling future. Its enduring popularity is a testament to the lasting impact of Jennings and Nelson’s collaboration and the song’s timeless message.
Decades later, the song remains a beloved classic, reminding us of the enduring bond between parents and their children, and the hope for a bright future ahead.
We all know that Waylon Jennings has left an indelible mark on the world of country music with his incredible body of work. It’s no easy task to choose just ten of his songs as the absolute best. So, here’s where you come in! We want to hear from you and discover your favorite Waylon Jennings songs that you believe deserve a spot on this list.
In the comments section below, share your top picks and let us know which songs have touched your heart, made you tap your feet, or simply become the soundtrack to your life. It’s a chance for us to celebrate the diverse musical journey that Waylon Jennings took us on and to explore the different songs that resonated with each of us in a unique way.
Whether you’re drawn to his rebellious anthems, heartfelt ballads, or foot-stomping classics, we want to hear it all. So, don’t hold back! Share your favorite Waylon Jennings songs and join the discussion with fellow fans. Together, let’s honor the incredible legacy of this country music legend and keep the spirit of his music alive for generations to come.