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Waylon Arnold Jennings (1937-2002) was a Country Music artist. He was known as one of the frontrunners for the "outlaw country" sound of The Seventies, joining Willie Nelson and Merle Haggard in that regard.

Jennings first worked with Buddy Holly in the 1950s, nearly losing his life prematurely in the notorious airplane crash that killed Holly et al. (He gave his seat to The Big Bopper.) After a failed single for A&M Records, he recorded for RCA from 1965 through 1986, first reaching #1 in 1974 with "This Time." A guest appearance on Wanted! The Outlaws -- a multi-artist album which was the first country music album ever to earn a platinum certification -- kicked his career into high gear.

Many of his songs, including "I'm a Ramblin' Man," "Are You Sure Hank Done It This Way," "Luckenbach, Texas (Back to the Basics of Love," are considered cornerstones of country music. His biggest crossover hit was the "Theme from The Dukes of Hazzard (Good Ol' Boys)." By the mid-eighties, the hits started to MCA Records brought only a handful of hits, including his last #1, "Rose in Paradise." He moved again to Epic Records in 1990, managing the #5 "Wrong," the last big hit of his career, but he continued to record consistently until complications of diabetes brought his career to an end.

Tropes present:

  • Generation Xerox: His son, Shooter, in 2006, released his first album, titled Put The 'O' Back In Country.
  • I Wished You Were Dead: A rather tragic example. After Buddy Holly won a coin flip, Jennings was forced to take a bus to Minnesota while Holly took a plane. When Holly joked "I hope your bus freezes!", Jennings joked back "I hope your damn plane crashes!". Jennings was haunted by those words for years.
  • Lampshade Hanging: He released a song titled "Don't You Think This Outlaw Bit's Done Got Out of Hand."
  • Three Chords and the Truth: The outlaw sound that Jennings helped forge is known for its simple, raw production and lyrics.
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