... he died on February 13, 2002 at the age of 64.
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Jennings escaped death in the February 3, 1959, plane crash that took the lives of Buddy Holly, Ritchie Valens, and J.P. "The Big Bopper" Richardson, when he gave up his seat to Richardson who had been sick with the flu. According to folklore, Jennings and The Big Bopper flipped a coin for the last seat on the plane, with Jennings losing. It was Tommy Allsup who flipped the coin for the fated plane trip, losing his seat to Valens.
In his 1996 autobiography, Jennings admitted that he suffered guilt and responsibility for the crash for decades. After Jennings had given up his seat, Holly jokingly told Jennings, "I hope your ol' bus freezes up!"
Jennings shouted back, "Well, I hope your ol' plane crashes!"
Waylon Arnold Jennings was born in Littlefield, Texas. When he was eight, his mother bought him his first guitar, and taught him how to play. Waylon formed his first band two years later. Waylon was kicked out of music class at school for lack of musical ability; he never learned to read music.
During his time working as a DJ, he befriended Buddy Holly. When he was twenty-one, Jennings was tapped by Holly to play bass in Holly's new band on a tour through the Midwest in early 1959. Holly also hired guitarist Tommy Allsup and drummer Carl "Goose" Bunch for the "Winter Dance Party" tour.
After several years of inactivity following Holly's death, Jennings moved from Texas to Arizona and continued working in radio, Jennings began performing and recording again. He signed a contract with Herb Alpert's newly-formed A&M Records, and he had a few hit singles on local radio in Phoenix, including "Four Strong Winds" and "Just To Satisfy You."
He also recorded an album on the BAT label, called simply JD's. He also played lead guitar for Patsy Montana on a record album that she recorded in Arizona in 1964.
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-----Duane Eddy and Bobby Bare recommended Jennings to producer Chet Atkins, who signed Waylon to RCA Victor. Bobby Bare did his own cover of "Four Strong Winds" after he heard Jenning's version. Still under contract to A&M, Alpert released him which allowed him to sign with RCA Records. Jennings packed up and moved to Nashville, Tennessee in 1965.
Jennings was accustomed to performing and recording with his own band, The Waymores; this was a practice that was not encouraged by Nashville producers who controlled nearly every aspect of recording. Over time, however, Jennings felt limited by the Nashville sound and the lack of artistic freedom that came with it, in the 1960s country music industry.
Jennings had grown more frustrated with the Nashville recording scene and a 1972 bout with hepatitis almost killed him. With his recording contract nearing an end, RCA had already lost another creative force that year: Jennings had met Willie Nelson, who had likewise felt frustrated by the lack of freedom in the studio and by the Nashville scene which led him to relocate his base to Texas, two years earlier.
Jennings seriously considered returning to a broadcasting career in Phoenix. By the 1970s, Jennings had become associated with so-called "outlaws," an informal group of musicians who worked outside of the Nashville music establishment.
A series of duet albums with Willie Nelson in the late '70s culminated in the 1978 crossover hit, "Mammas Don't Let Your Babies Grow Up to Be Cowboys." In 1979, he recorded the theme song for the hit television show The Dukes of Hazzard, and also served as the narrator ("The Balladeer") for all seven seasons of the show.
He continued to be active in the recording industry, forming the group The Highwaymen with Nelson, Johnny Cash, and Kris Kristofferson. Jennings released his last solo studio album in 1998.
In 1999, Jennings assembled what he referred to as his "hand-picked dream team" - and formed Waylon & The Waymore Blues Band. Consisting primarily of former Waylors, the thirteen-member group performed a limited number of concerts at select venues, from 1999 to 2001. The highlight of this period was the January 2000 recording, at Nashville's historic Ryman Auditorium, of what would become Jennings' final album, Never Say Die: Live.
An abbreviated album, composed of 14 tracks, was released in October 2000. A special edition box set, including all twenty-two tracks on two audio CDs, as well as a DVD with the complete concert and bonus features, was released on July 24, 2007 from Legacy Recordings.
In 2001, he was inducted into the Country Music Hall of Fame. On June 20, 2007, Jennings was posthumously awarded the Cliffie Stone Pioneer Award by the Academy of Country Music.