(1937----) Birthplace: Littlefield Genre: Country Western Other Sites: Waylon Jennings Official Webpage

Waylon Jennings was the original outlaw of country, and the first to tire of posing as a bad boy. But the outlaw image served to make Waylon Jennings a media personality and star, just as it did Willie Nelson. His record sales skyrocketed with the release of Wanted: The Outlaws and made possible a lengthy career that continued into the nineties until ill health forced him into semi-retirement.

Jennings was no newcomer to the music scene when he led the so-called Outlaw rebellion against the Nashville country music establishment in the early seventies. In fact, although Ernest Tubb was his boyhood hero as he was growing up in Littlefield and Lubbock, Buddy Holly was the friend who produced Jennings' first recording, "Jole Blon," in 1958. Son of a dancehall guitarist, Jennings was hired to play bass with Buddy Holly's Crickets on the ill-fated tour that ended Holly's promising career. Jennings gave up a seat on the doomed plane to the Big Bopper.

For a time after the crash, Jennings went back to Lubbock and took a job broadcasting but soon returned to music. He moved to Phoenix and formed a group, the Waylors, which played regularly at the Phoenix Club for two years, starting in 1964. The gig led to a first album, Waylon Jennings at J.D.'s and a second unfocused folk, pop, country, rock album titled after the Bob Dylan song "Don't Think Twice" it contained that was just good enough to get the attention of producer Chet Atkins at RCA.

Waylon's luck -- and experience -- paid off with his first country music recording for the label, "That's the Chance I'll Have to Take," which made the country charts. With 1971's Singer of Sad Songs, the melancholy tendency in his voice was used to good effect. But as he continued to have hits in the heavily arranged style of Nashville in that period -- "Love of the Common People" and "Only Daddy That'll Walk the Line" -- he grew dissatisfied. He was living a lifestyle, complete with long hair, which was a disputed option for a country star at the time. But the main issue was over control of production, which included the selection and arrangement of music. Jennings discovered the songs of Kris Kristofferson and included them on The Taker/Tulsa (1971). He also liked Billy Joe Shaver's songs, putting them on Honky Tonk Heroes (1973).

By some accounts, the persona Jennings projected in such songs as "Ladies Love Outlaws," and "Lonesome, On'ry and Mean," combined with album jacket photos of Jennings' dark clothing and deeply lined face, led directly to the outlaw image of the RCA collection Wanted: The Outlaws. Others see it all as a marketing ploy. Whatever the truth of the matter, the 1976 album went platinum, a first for a country music album. Featuring the talents of Willie Nelson, Jessi Colter and Tompall Glaser, it also represents a turning point from Jennings' driven career to a more relaxed period of music-making among friends. A series of Waylon and Willie collaborations was followed by further collaborations with Kris Kristofferson, and that other man in black, Johnny Cash -- all of which sold well. Other projects that might not otherwise have been possible under the old Nashville restraints include the autobiographical A Man Called Hoss (1987), The Eagle (1990), and the wonderfully funny, Too Dumb for New York City -- Too Ugly for L.A. But if Waylon was an outlaw, he also had a gentler side, which came out in such songs as "Luckenbach, Texas," and the song that questioned, "Don't You Think This Outlaw Bit's Done Got Out of Hand?"

In 1993 both Johnny Cash and Jennings had heart attacks and arranged to recuperate in adjacent hospital beds. They also announced that they would not be working together as the Highwaymen in the future.