Waylon Arnold Jennings (June 15, 1937 -- February 13, 2002) was a CountryMusic artist. He was known as one of the frontrunners for the "outlaw country" sound of TheSeventies, joining Music/WillieNelson and Music/MerleHaggard in that regard.

Jennings first worked with Music/BuddyHolly 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 Creator/RCARecords 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 ''Series/TheDukesOfHazzard'' (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 Creator/EpicRecords 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.

Jennings was married to singer Jessi Colter, best known for her hit single "I'm Not Lisa". Their son, Shooter, is a fairly well-known alternative-country artist.

!! Tropes present:
* CityShoutOuts: "Luckenbach, Texas" (yes, it's a real town, though neither Jennings nor the song's writers had ever been there).
* TheCityVsTheCountry: "Luckenbach" again.
-->This coat and tie is chokin' me, and in your high society you cry all day
-->We've been so busy keepin' up with the Jones'
-->Four-car garage and we're still buildin' on
-->Baby, it's time we got back to the basics of love... let's go to Luckenbach, Texas...
* ClipShow: His 1983 album ''It's Only Rock & Roll'' ends with a medley of re-recorded versions of eight of his biggest hits.
* ConceptAlbum: ''A Man Called Hoss''.
* DoNotDoThisCoolThing: {{Invoked|Trope}} with "Mamas, Don't Let Your Babies Grow Up To Be Cowboys".
* EarlyInstallmentWeirdness: Jennings always drew from a wide range of influences, which left RCA struggling to figure out how to market him in the 60s. They ended up labeling his style as [[NeoclassicalPunkZydecoRockabilly "folk country"]] (as opposed to "folk rock"), but no one really understood what that was supposed to mean; he even had the original hit version of "[=MacArthur=] Park" (which was made far more famous by disco diva Music/DonnaSummer). His producers tried to fit his eclectic style into standard Nashville formulas with mixed results. It wasn't until the birth of the "outlaw" movement in the early 70s that he found a comfortable fit.
* GenerationXerox: His son Shooter, in 2006, released his first album, titled ''[[AwesomeMcCoolname Put The 'O' Back In]] [[CountryMatters Country]]''. Shooter also played his father in the movie ''Film/WalkTheLine''.
* IWishedYouWereDead: A rather tragic example. After Music/BuddyHolly won a coin flip, Jennings was forced to take a bus to Minnesota while Holly took a plane. Holly joked "Well, I hope your ol' bus freezes up." Jennings joked back "[[FunnyAneurysmMoment Well, I hope your ol' plane crashes.]]" [[SurvivorGuilt He was haunted by those words for the rest of his life.]]
* LampshadeHanging: He released a song titled "Don't You Think This Outlaw Bit's Done Got Out of Hand."
* ListingCities: "I'm a Ramblin Man".
* MurderBallad: "Cedartown, Georgia". The song ends before the actual murder, but you don't doubt that the narrator's going to go through with it.
* NarratorAllAlong: "Good-Hearted Woman". The third singing of the chorus shifts from third to first person.
* PartingWordsRegret / SurvivorGuilt: After "The Day the Music Died", Jennings admitted he felt he shouldn't have jokingly cursed Holly's plane to crash after losing his plane seat to him in a coin flip.
* PossessiveParadise: His 1987 No. 1 hit "Rose in Paradise," where the title character, an incredibly beautiful young woman, marries a rich banker ... and not long after the marriage she becomes a prisoner in their home -- he had sold his promises of a carefree life of luxury to her as "paradise" -- and becomes so possessive of her to the point where he hires a gardener to make sure she never escapes, even when the banker himself is gone on his extended business trips.
* SuperGroup: The Highwaymen with Music/WillieNelson, Music/JohnnyCash, and Music/KrisKristofferson.
* ThreeChordsAndTheTruth: The outlaw sound that Jennings helped forge is known for its simple, raw production and lyrics.