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Go back and check out his early recordings for RCA, and you will find some work that is astonishing in scope and talent. In this discussion of Waylon Jennings songs, we keep the focus on his solo work. And, as you can imagine, the majority of the selections on this list are from onward, when he began to capture lightning in a bottle. But, there are a few of his early hits that deserve a mention as well! Critics have been mixed of his recorded output there, but he did take a few musical chances that were worth noting. By , Jennings had his sound down almost to an exact science, and this No. This top ten is noteworthy for his vocal performance, which is one of his more restrained in his catalog. Vocally, the singer held back just a little bit on this gem of a song, and the result was one of his early moments that gave fans a hint at the style in which he was seeking to establish.
"Rose in Paradise"
Throughout his career, however, he remained an honest artist fighting to record the music inside him the way he wanted to hear it. Jennings' career began in , when he became a member of Buddy Holly's Crickets. After Holly's death one year later, on Feb. Below, Taste of Country has compiled a list of songs that best represent the career of this legendary outlaw, from popular Willie Nelson duets to the theme from The Dukes of Hazard to final chart toppers including "Wrong" and "Rose in Paradise. In , Jennings proved that he still had a few hits left in him, even though he was already considered a legend. The Class of '89 -- Garth Brooks , Clint Black , Alan Jackson and Travis Tritt -- were starting to control the charts with the new, young country movement, leaving less room for the veterans of the genre. The humorous single accompanied by a comical video gave Jennings the final Top 5 hit of his career. Not only was it a No. It would be no more a surprise to hear a family singing this song around a campfire than it would be to hear it blaring in a crowded honky-tonk. In , Jennings earned the final No.
Below, The Boot takes a look at our picks for 10 of Jennings' best tunes. The song, which became Jennings 12th No. They took her to trial and they could never prove that she poisoned any of them. 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. Ray Pennington wrote and originally recorded "I'm a Ramblin' Man," and Jennings became a fan of his version.