Waylon Jennings was an American country music singer, songwriter, and musician, born on June 15, 1937, in Littlefield, Texas. He was a pivotal figure in the outlaw country movement that arose in opposition to the polished and highly produced Nashville sound that dominated mainstream country music. Jennings began his music career at a young age, initially gaining some fame as a bassist for Buddy Holly. He fortuitously gave up his seat on the ill-fated flight that killed Holly, J.P. “The Big Bopper” Richardson, and Ritchie Valens in 1959, a decision that haunted him but also gave him a sense of urgency about his career.
In the 1960s, Jennings signed with RCA Records and started working with producer Chet Atkins, who was instrumental in shaping the Nashville sound. While Jennings had some success during this period with songs like “Only Daddy That’ll Walk the Line” and “The Taker,” he grew increasingly dissatisfied with the creative restrictions imposed by the Nashville system. It wasn’t until the 1970s that he gained full control over his records, including the selection of songs and musicians and the choice of producer. This creative freedom led to seminal albums like Honky Tonk Heroes and Dreaming My Dreams, which crystallized the rugged, independent style of outlaw country. During this period, he also teamed up with Willie Nelson, Jessi Colter (his wife), and Tompall Glaser to record the groundbreaking album Wanted! The Outlaws, which was the first country album to be certified Platinum.
Jennings’ music often dealt with themes of rebellion, individualism, and a relentless quest for authenticity. His iconic songs like “Good Hearted Woman,” “Luckenbach, Texas,” and “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” serve as milestones in country music history, blending elements of rock and roll into the country genre. Known for his deep, resonant voice and charismatic stage presence, he also made significant contributions to television, notably through the theme song and narration for the series The Dukes of Hazzard.
Waylon Jennings struggled with drug addiction for a portion of his life, but eventually, he overcame his issues and continued to perform until his health began to decline. He was inducted into the Country Music Hall of Fame in 2001. Sadly, he passed away on February 13, 2002, due to complications from diabetes, but his influence on country music remains indelible. His anti-establishment ethos, combined with his immense musical talent, makes him one of the most enduring and fascinating figures in the history of American music.
Top 10 Waylon Jennings Songs
#10 – Theme from The Dukes of Hazzard (Good Ol’ Boys)
The song “Theme from The Dukes of Hazzard (Good Ol’ Boys)” was performed by Waylon Jennings and served as the theme song for the television show The Dukes of Hazzard, which aired from 1979 to 1985. Jennings, who also narrated the TV series, recorded the song at Moman’s American Studios in Nashville, Tennessee. The track was produced by Richie Albright, Waylon Jennings’ longtime drummer and producer. While details on all the musicians involved in the recording session might not be readily available, Jennings himself played guitar and provided the lead vocals.
Upon its release as a single in 1980, the song became a massive hit, reinforcing Jennings’ prominence in the country music scene. It reached the number one spot on the Billboard Hot Country Singles chart and crossed over to pop charts, peaking at number 21 on the Billboard Hot 100. The song resonated with fans of both the television show and country music in general, largely because it encapsulated the show’s themes of southern pride, family, and anti-establishment sentiments. Its mainstream success helped blur the lines between country and popular music, further illustrating the broad appeal of the outlaw country genre that Jennings had helped pioneer.
#9 – Rose in Paradise
The first single “Rose in Paradise” comes from the 1987 album “Hangin’ Tough” and spent nineteen weeks on the US Billboard Hot Country Songs chart and peaked at number one for one week. It also ranked first on the Canadian RPM Country Tracks chart. It is among one of seventeen number one hits Waylon Jennings would realize as a singer-songwriter of the country music genre. What makes this song stand out, mainly among women, is how some perhaps related to the heroine in the song whose marriage to a rich banker should have been paradisic but fell short due to his possessiveness.
#8 – Just to Satisfy You (featuring Willie Nelson)
With the US Hot Country Songs chart, “Just to Satisfy You” peaks at number one while peaking as high as second with RPM Canada. The duet comes from the album “Black on Black,” which was released in 1982. This version proved to be considerably more successful than when it was first recorded and released in 1963 by Waylon Jennings and Don Bowman.
#7 – MacArthur Park (featuring The Kimberleys)
During the 1969 Grammy Awards, the hit single “MacArthur Park” earned Waylon Jennings the win for Best Country Performance by a Duo or Group with Vocals. While the single didn’t reach number one on the big music charts, it still performed well enough to rank at #11 with Canada’s RPM, #23 on the US Billboard Hot Country Songs chart. The Jimmy Webb song has been recorded by many artists over the years with Richard Harris and Donna Summer having the most success with the song.
#6 – Amanda
The first time Waylon Jennings recorded and released his cover of “Amanda” was in 1974 and received moderate chart success. The new and improved version in 1979 came out with his “Greatest Hits” album, realizing far greater chart success by peaking at number one with the US Billboard Hot Country Songs and Canada’s RPM.
#5 – Highwayman
Collaborating as Highwaymen with fellow country music outlaws, Johnny Cash, Kris Kristofferson, and Willie Nelson, the single “Highwayman” stems from the 1984 album of the same name. On the charts, it peaked at number one with the US Billboard Hot Country Songs and with Canada’s RPM. It also won Single of the Year in 1985 by the Academy of Country Music.
#4 – Good Hearted Woman (featuring Willie Nelson)
Whether it be strictly Waylon Jennings performing “Good Hearted Woman” or is paired up with Willie Nelson, the song is a solid favorite among country music fans. The duet version received a Single of the Year in 1976 from the Country Music Association. On the music charts, the singular performance by Jennings saw Good Hearted Woman peak at number one with Canada’s RPM chart while placing third with the US Billboard Hot Country Songs. The duet performance including Willie Nelson, saw this song peaking at number one with the US Billboard Hot Country Songs chart while placing fifth with Canada’s RPM. The duet version of this song also realized crossover success by charting at #25 on the US Billboard Hot 100, as well as #16 on the US Billboard Adult Contemporary chart.
#3 – I’m a Ramblin’ Man
Peaking at number one with the US Billboard Hot Country Songs chart and in second with Canada’s RPM, the 1974 single “I’m a Ramblin’ Man” comes from the album of the same name. Among country music fans, this song continues to be something of a self-proclamation of their own as they find themselves relating to Jennings.
#2 – Luckenbach, Texas (Back to the Basics of Love)
The album “Ol’ Waylon” was released in 1977 with the single “Luckenbach, Texas (Back to the Basics of Love).” With the music charts, it peaked at number one with the US Billboard Hot Country Songs and Canada’s RPM. It was also a crossover hit, charting at #16 on the US Billboard Adult Contemporary charts, and at #25 on the US Billboard Hot 100.
#1 – Mammas Don’t Let Your Babies Grow Up to Be Cowboys (featuring Willie Nelson)
Between the US Billboard Hot Country Songs and Canada’s RPM chart, the duet performance of “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” charted at number one. It also won Best Country Vocal Performance By a Duo or Group during the 1978 edition of the Grammy Awards. It is also one of the most commercially successful country music hits that still receives many requests by music fans of the country music genre.
Updated October 31, 2023
Top 10 Waylon Jennings Songs article published on Classic RockHistory.com© 2023
Classicrockhistory.com claims ownership of all its original content and Intellectual property under United States Copyright laws and those of all other foreign countries. No one person, business, or organization is allowed to re-publish any of our original content anywhere on the web or in print without our permission. All photos used are either public domain Creative Commons photos or licensed officially from Shutterstock under license with ClassicRockHistory.com. All photo credits have been placed at the end of the article. Album Cover Photos are affiliate links and the property of Amazon and are stored on the Amazon server. Any theft of our content will be met with swift legal action against the infringing websites.