Throughout his illustrious career, Jennings released more than 80 albums and charted over 60 singles. Below, The Boot takes a look at our picks for 10 of Jennings' best tunes.
"Rose in Paradise"From: 'Hangin' Tough' (1987)
Written by Jim McBride and Stewart Harris, "Rose in Paradise" was Jennings' debut single from Hangin' Tough. The song, which became Jennings 12th No. 1 hit, was inspired by a woman named Rose, who, in the 1800s, presumably killed all five of her husbands.
"I was telling him about this house back home, outside of Huntsville, Alabama, where in the 1800s this lady named Rose lived," McBride tells The Boot. "She had five well-to-do husbands, and they all died mysteriously. They took her to trial and they could never prove that she poisoned any of them."
"Rose in Paradise" became Jennings' final No. 1 hit.
"Are You Sure Hank Done It This Way?"From: 'Dreaming My Dreams' (1975)
Jennings paid tribute to Hank Williams with this tune, which questioned the trajectory of country music with lines such as, "Lord it's the same old tune, fiddle and guitar / Where do we take it from here? / Rhinestone suits and new shiny cars / It's been the same way for years / We need to change." The No. 1 hit has been covered by Clint Black, Robert Earl Keen, Jack Ingram and others.
"Highwayman"From: 'Highwayman' (1985)
"Highwayman" was the first single released from the quartet the Highwaymen, and their only single to reach the top of the charts. Written by Jimmy Webb, "Highwayman" was first released by both Webb and Glen Campbell, before Marty Stuart convinced the Highwaymen to record it as well.
"Luckenbach, Texas (Back to the Basics of Love)"From: 'Ol' Waylon' (1977)
"Luckenbach, Texas" stayed on top of the charts for six weeks, becoming one of the most successful songs of Jennings' career. The song, which is about a rich couple whose money is driving them apart, references Jennings himself, as well as Nelson, Williams and Jerry Jeff Walker.
"I've Always Been Crazy"From: 'I've Always Been Crazy' (1978)
"I've Always Been Crazy" is the title track of Jennings' 25th studio album and includes lines such as, "I've always been crazy and the trouble that it's put me through / I've been busted for things that I did, and I didn't do / I can't say I’m proud of all of the things that I’ve done / But I can say I’ve never intentionally hurt anyone." The icon wrote the song as a statement, after yet another drug bust, due to Jennings' lengthy history with cocaine.
"It was a media feeding frenzy, like sharks smelling blood in the water," Jennings later shared in his autobiography, Waylon: An Autobiography. "I couldn't go anywhere without a cluster of reporters swarmin' around me."
"Theme From 'Dukes of Hazzard' (Good Ol' Boys)"From: 'Music Man' (1980)
Jennings sang the theme song for the hit TV show Dukes of Hazzard and also served as the show's narrator, but the TV version of the song was slightly different than its radio version: On Dukes of Hazzard, the song included the lines "Fightin' the system like two modern-day Robin Hoods," while the radio version added "You know my momma loved me, but she don't understand, they keep showing my hands and not my face on TV," in reference to the fact that the show's producers did just that.
"Good Hearted Woman"From: 'Good Hearted Woman' (1972)
"Good Hearted Woman" was the title track of Jennings' 16th studio album. Written by Jennings and Nelson, the song was inspired while Jennings and Nelson were traveling together and saw a sign, advertising Ike and Tina Turner, that said she was a "good-hearted woman loving two-timing men." Jennings and Nelson wrote the song while playing poker, with Nelson's then-wife Connie Koepke writing the lines down as they said them.
"I'm a Ramblin' Man"From: 'The Ramblin' Man' (1974)
Ray Pennington wrote and originally recorded "I'm a Ramblin' Man," and Jennings became a fan of his version. For years, Jennings promised to record "I'm a Ramblin' Man," but it wasn't until Pennington wrote another song that Jennings wanted that he finally made good on that promise.
“I loved Ray’s record of it,” Jennings said, “and when we got into the studio, he had another song I wanted, "Oklahoma Sunshine." That was the one I really wanted, and I said, 'Ray, if you’ll let me do "Oklahoma Sunshine," I’ll record "I’m a Ramblin’ Man," too, and let you produce ‘em.’”
"Amanda"From: 'Greatest Hits' (1979)
"Amanda" was written by Bob McDill and first recorded by Don Williams. Jennings also recorded "Amanda" in 1974, for his The Ramblin' Man album, but he didn't release it as a single until he included it on his Greatest Hits album. The song stayed at the top of the charts for three weeks and was nominated for both a CMA Award and an ACM Award, for Single of the Year.
"Mammas Don't Let Your Babies Grow Up to Be Cowboys"From: 'Waylon & Willie' (1978)
In this song, which was written by husband-and-wife songwriting partners Ed and Patsy Bruce, Jennings and Nelson sing lines such as "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 / Mamas don't let your babies grow up to be cowboys / 'Cos they'll never stay home and they're always alone / Even with someone they love." Jennings originally recorded the song by himself, before deciding it would sound better as a duet. "Mammas Don't Let Your Babies Grow Up to Be Cowboys" stayed in the No. 1 spot for four weeks, helping the Waylon & Willie album stay in the top spot for 10 weeks.