Was briefly a member of Buddy Holly's band as the bass player.
He was married and divorced three times before marrying Jessi Colter.
Was supposed to be on the flight that killed Buddy Holly, Ritchie Valens and The Big Bopper. The Big Bopper was sick and wanted to fly rather than ride the tour bus, so Jennings gave him his seat on the plane.
Ended a 20-year cocaine addiction in 1984. At times, he was spending $1500 a day on the drug.
High school dropout who got his General Educational Development (GED) in 1989.
Had have his left foot amputated due to diabetes in December 2001.
He made occasional forays into television movies, including Stagecoach (1986) and The Oklahoma City Dolls (1981), plus the Sesame Street movie Follow That Bird (1985) and a low-budget country/western musical, Nashville Rebel (1966).
In the mid-1980s, he joined with Willie Nelson, Johnny Cash and Kris Kristofferson to form the quartet The Highwaymen, which recorded together and did concert tours.
"I'd like to be remembered for my music-- not necessarily by what people see when they see us-- but what they feel when they talk about you," he said in 1984.
His "Greatest Hits" album in 1979 sold four million copies--a rare accomplishment in country music for that era.
His other hit singles included "I'm a Ramblin' Man", "Amanda", "Lucille", "I've Always Been Crazy" and "Rose in Paradise".
Named Male Vocalist of the Year by the Country Music Association in 1975.
Won a Grammy Award for a version of "MacArthur Park" recorded with The Kimberleys.
He sold more than 40 million albums and singles worldwide, including 16 #1 country hits.
Survived by Jessi Colter, his fourth wife, and seven children.
When he was told by doctors to quit touring, he auctioned off much of his equipment. Less than a year later, though, he was back playing concerts.
He often refused to attend music awards shows on the grounds that performers should not compete against each other. Despite those sentiments, he won two Grammy Awards and four Country Music Association Awards. He did not attend his induction into the Country Music Hall of Fame in 2001.
Son (with Jessi Colter) Shooter Jennings (b. Waylon Albright Jennings, 1979) sings with the Los Angeles band Stargunn.
Worked as a disc jockey at a Lubbock, Texas radio station.
Jokingly told his friend Buddy Holly that he hoped his plane crashed, after he gave up his own seat, but was said to be extremely remorseful of the light-hearted comment and for years felt somehow responsible for his friend's death.
Stevie Nicks wrote her 1981 hit "Leather & Lace" at Jennings' request, as a song for he and wife Jessi Colter. It was his intent that they would record the song at a future time. However, by the time Nicks finished penning the song, Waylon and Jessi had split. Nicks recorded it with Don Henley (of Eagles). The Nicks/Henley version was included on her 1981 LP "Bella Donna" and went to #6 on the US charts. Waylon and Jessi never made a studio recording of the song.
He claimed that his guitarist Jimmy Byrd was the only other man who could perform his trademark "Chicken Picking" style of guitar playing and often called him "Abe Lincoln" due to his resemblance to former president Abraham Lincoln.
He was usually regarded as the unifying, central force of "The Highwaymen", as he brought together Johnny Cash, Willie Nelson and Kris Kristofferson, all of whom he had been friends with since the 1960s.
Is portrayed by his son Shooter Jennings in Walk the Line (2005).
His former home in Brentwood, Tennessee, is named "Southern Comfort".
Inducted into the Nashville Songwriters Hall of Fame in 1995 and the Country Music Hall of Fame in 2001.
Smoked six packs of cigarettes a day until undergoing triple heart bypass surgery in December 1988.
Narrated the trailer for Moonrunners (1975), a film about moonshine runners in which he also stars as the storyteller.
Is one of the Four Horsemen of the Country Music Apocalypse along with Willie Nelson, Kris Kristofferson and Johnny Cash.