Top 10 Waylon Jennings Songs list looks at a country music artist for bringing a grittier personality toward the country music genre. Born out of Littlefield, Texas on June 15, 1937, Jennings grew up during the post-WWII era where Americans were recovering from the aftermath of a world war while still venturing forward with new discoveries. This includes the genre of country music where a then twelve-year-old Jennings worked as a disc jockey for a local radio station, as well as playing guitar among different bands. Over time, Jennings developed a country music style that saw a heavy influence of bass instrumentation. At one point, after befriending and performing with Buddy Holly, Jennings was supposed to board a private plane with Holly and Ritchie Valens but gave up his seat to J.P. “The Big Bopper” Richardson. This is the same private plane that would crash and claim their lives on February 3, 1959.
Outlaws and Highwaymen
Since moving to Lubbock, Texas as of the mid-1950s, which he returned to after the infamous plane crash, Jennings focused on his country music. Jennings and country musicians were often considered outlaws within the industry for often challenging the traditional style of country music by integrating rock-and-roll accents into their performances. One challenge in particular that stands out had Jennings depart from A&M Records after they attempted to have him focus on the rock music genre instead of country. This prompted him to leave, not wanting to conform to the commercialistic expectations that would take him away from his own identity.
Waylon Jennings, along with his fellow outlaws, were also notorious for their party-hard ways, which became a costly habit he finally learned to kick to the curb in 1984. In 1985, Jennings co-founded the country music band Highwaymen alongside Johnny Cash, Kris Kristofferson, and Willie Nelson. While the first album “Highwayman” they released together was a commercial success when it came out in 1985, the follow-up album “Highwayman 2” was not when it came out in 1990.
Despite the diagnosis of diabetes in the early 1990s, plus the lack of radio time his more recently recorded music was receiving at one point, this didn’t stop Waylon Jennings from performing. Between touring and recording, he continued until his ailing body wasn’t able to keep up anymore. On February 13, 2002, Waylon Jennings passed away in his home in Chandler, Arizona. The music legacy Jennings leaves behind a total of 45 studio albums, five live albums, 28 compilation albums, 16 collaborated albums, as well as a grand total of 96 singles.
Top 10 Waylon Jennings Songs
#10 – Theme from The Dukes of Hazzard (Good Ol’ Boys)
Fans of the television series “The Dukes of Hazzard” will remember best how the start of each episode featured the performance of Waylon Jennings’s “Theme from The Dukes of Hazzard (Good Ol’ Boys)” It was the second single from his 1980 album “Music Man.” which charted to number one with the US Billboard Hot Country Songs. It also achieved second place with the Canadian RPM Country Tracks chart. The series ran from 1970 until 1985, featuring what is among the most beloved theme songs to a television show of all time.
#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 records and releases 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 with US Billboard Adult Contemporary, and at #25 with 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.