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 Records 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.
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.
- City Shout Outs: "Luckenbach, Texas" (yes, it's a real town, though neither Jennings nor the song's writers had ever been there).
- The City vs. the Country: "Luckenbach" again.This coat and tie is chokin' me, and in your high society you cry all dayWe've been so busy keepin' up with the Jones'Four-car garage and we're still buildin' onBaby, it's time we got back to the basics of love... let's go to Luckenbach, Texas...
- Also "Where Corn Don't Grow" (later covered by Travis Tritt), where the lead singer asks why his dad never thought about moving to the city. His dad basically gives him a "grass is always greener" Aesop. The third verse reveals the singer decided to go to the city anyway, finding it just as hard if not worse than the country.
- Clip Show: His 1983 album It's Only Rock & Roll ends with a medley of re-recorded versions of eight of his biggest hits.
- Concept Album: A Man Called Hoss.
- Do Not Do This Cool Thing: Invoked with "Mamas, Don't Let Your Babies Grow Up To Be Cowboys".
- Early Installment Weirdness: 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 "folk country" (as opposed to "folk rock"), but no one really understood what that was supposed to mean; he even had a Grammy Award-winning version of "MacArthur Park" (which was made far more famous by disco diva Donna Summer). 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.
- Generation Xerox: His son Shooter, in 2006, released his first album, titled Put The 'O' Back In Country. Shooter also played his father in the movie Walk the Line.
- Gratuitous French: His first single was a 1958 version of the Cajun standard "Jole Blon", sung in Cajun French, even though neither Jennings nor producer Buddy Holly knew the language. Jennings just learned the lyrics phonetically.
- I Wished You Were Dead: A rather tragic example. Buddy Holly chartered a plane to fly Jennings and himself to Fargo, but Jennings graciously gave up his seat to an ailing Big Bopper. When Holly found out Jennings was going on the bus instead, he joked "Well, I hope your ol' bus freezes up." Jennings joked back "Well, I hope your ol' plane crashes." He was haunted by those words for the rest of his life.
- Lampshade Hanging: He released a song titled "Don't You Think This Outlaw Bit's Done Got Out of Hand."
- Listing Cities: "I'm a Ramblin Man".
- Murder Ballad: "Cedartown, Georgia". The song ends before the actual murder, but you don't doubt that the narrator's going to go through with it.
- Narrator All Along: "Good-Hearted Woman". The third singing of the chorus shifts from third to first person.
- Parting Words Regret / Survivor Guilt: 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.
- Possessive Paradise: 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.
- "Sesame Street" Cred: Appeared in Sesame Street Presents: Follow That Bird as a turkey truck driver who gives Big Bird a ride and sings "Ain't No Road Too Long" with him. He also made an appearance on the show in The '90s.
- Super Group: The Highwaymen with Willie Nelson, Johnny Cash, and Kris Kristofferson.
- Three Chords and the Truth: The outlaw sound that Jennings helped forge is known for its simple, raw production and lyrics.