- Was originally named Wayland, but his mother changed the spelling because a preacher assumed she named him after the local college. It was never changed on his birth certificate.
- Started as a disc jockey when he was just 12 years old.
- Gave up his seat on the airplane that would eventually crash and take the lives of the Big Bopper, Buddy Holly and Ritchie Valens in 1959.
- Was a member of the Highwaymen, a band that also consisted of Kris Kristofferson, Johnny Cash and Willie Nelson; they were credited with bringing country back to its roots.
- Sang the theme song for The Dukes of Hazzard and was the off-screen narrator for the show.
- Struggled with a decades-long addiction to cocaine; claimed that he often spent more than $1500 a day to support the habit.
- Earned his GED in 1989 at the age of 52.
- Released a children's album, Cowboys, Sisters, Rascals & Dirt, in 1993.
- His son Shooter Jennings played him in the 2005 movie Walk the Line.
- 1978, Grammy — Best Country Performance by a Duo or Group with Vocal: Winner
- 1969, Grammy — Best Country Performance by a Duo or Group with Vocal: Winner
- William Jennings — Father
- Lynn Mitchell — Ex-wife
- Buddy — Son
- Jessi Colter — Wife
- Jennifer Jennings — Stepdaughter
- Shooter Jennings — Son
- Barbara Rood — Ex-wife
- Deana — Daughter
- Terry — Son
- Maxine Carroll Lawrence — Ex-wife
- Bo Jennings — Brother
- Tommy Jennings — Brother
- James Jennings — Brother
- Tomi Lynn — Daughter
- Phillip Jennings — Brother
- Lorene Beatrice Shipley Jennings — Mother
- Julie — Daughter
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