His big break came when he was tapped by Holly to play bass in Holly’s new band on a tour through the Midwest in late 1958 and early 1959. In an oft-told tale, Jennings gave up his airplane seat to the Big Bopper, J. P. Richardson, for an ill-fated flight that would claim the lives of Holly, the Bopper, and singer Ritchie Valens. After the plane crashed, Jennings’s musical world crashed around him. Holly had been his mentor, producing his first record (“Jole Blon,” Brunswick, 1958), and Jennings felt responsible, because his last words to Holly had been the joking refrain, “I hope your ole plane crashes” (in response to Holly’s “I hope your damned bus freezes up again”).

It took Jennings years to regain some career equilibrium. He first went back to radio in West Texas, then began performing again, ending up at a bar in Phoenix, Arizona, called J. D.’s. Jennings became a local celebrity there, and when Nashville performer Bobby Bare passed through Phoenix and heard Jennings, Bare headed for a pay phone to tell his producer, Chet Atkins at RCA in Nashville, about this raw young talent out in Arizona.

Jennings had already cut some songs in a country-folk vein for then-fledgling A&M Records in Los Angeles, but A&M demurred to Atkins, who signed Jennings to RCA. The singer’s first session for RCA was held March 16, 1965.

Jennings moved to Nashville and, by sheer chance, became roommates with Johnny Cash; their legends as hellraisers soon became cemented. Jennings starred in the 1966 movie Nashville Rebel, scored Top Ten hits with songs such as “The Chokin’ Kind” (#8, 1967) and “Only Daddy That’ll Walk the Line” (#2, 1968), and his 1969 collaboration with the Kimberlys on “MacArthur Park” won a Grammy. But Jennings chafed under RCA’s tight rein, and at one point he also took a dramatic stand against the status quo: When Chet Atkins turned him over to staff producer Danny Davis, Jennings pulled out a pistol in the studio to protest Davis’s practice of what Jennings felt was studio bullying.

By the early 1970s Jennings was getting frozen out of country’s mainstream. He retaliated by hiring jazz musician Miles Davis’s maverick manager from New York City, who put him into such high profile venues as the rock-retro Max’s Kansas City in New York. Gradually, Jennings began to win his war in the studio. He stayed true to his musical instincts and recorded a gallery of landmark recordings, most notably the 1973 albums Lonesome, On’ry and Mean and Honky Tonk Heroes. He also staged an alternative show at the 1973 disc jockey convention in Nashville, with Willie Nelson, Sammi Smith, and Troy Seals joining him in an Outlaw program.

Jennings was dubbed an Outlaw in Nashville for demanding and eventually getting what rock groups had been used to having for years—namely, the right to record what material he wanted, in what studio he wanted, and with what musicians he wanted to use. (His friend Willie Nelson won his own independence by moving back to Texas and recording there.) It was, as Jennings later said, a simple matter of artistic freedom.

Jennings won CMA’s Male Vocalist of the Year Award in 1975, but what finally won the battle for Jennings and the Outlaws was the ultimate weapon in corporate wars: sales. Wanted! The Outlaws, an RCA package of songs by Jennings, Nelson, Jennings’s wife Jessi Colter, and Tompall Glaser, was released in January 1976, with only Jennings’s name credited on the album spine (since he was the only one of the four artists still under contract to RCA). The album flew out of record stores and soon became the first album in country music history to be certified platinum. The Jennings-Nelson duet “Good Hearted Woman” became a major crossover hit in 1976, as did Jennings’s “Luckenbach, Texas (Back to the Basics of Love)” the following year. Jennings and Nelson won a 1978 Grammy (Best Country Vocal Performance by a Duo or Group) for their hit “Mamas Don’t Let Your Babies Grow Up to Be Cowboys.” They (forever linked as “Waylon and Willie”) began selling records in numbers previously associated with rock album sales, and the Nashville system gradually moved away from a producer-dominated order to one in which the artist shares power.

Sadly, for the short term at least, Jennings’s excesses also paralleled those of the rock world. He was soon spending $1,500 a day on a cocaine habit that eroded his career. He eventually faced his addiction, beat it, and returned to a career much scaled down through stints on MCA and Epic through the late 1980s and early 1990s. He also became a bit of a role model by going back to earn his GED, or high school equivalency diploma. Jennings had dropped out of school in the tenth grade and felt he owed it to his young son to prove his resolution about the importance of education by finishing high school himself.

Jennings stopped touring in 1997 and died in 2002, shortly after his election to the Country Music Hall of Fame the year before. – Chet Flippo

– Adapted from the Country Music Hall of Fame® and Museum’s Encyclopedia of Country Music, published by Oxford University Press.