A true country outlaw, Waylon Jennings holds an enviable position as one of the pioneering figures behind contemporary country music. Jennings draws fans from every demographic, young and old, rural and urban, and people from every race, class and geographic location; fans are attracted to his loyalty to true, honky tonk roots .

Waylon Arnold Jennings grew up in Littlefield, Texas, where he began playing guitar at eight years old. By the age of 12, he was DJ'ing for a local radio station, and drumming up interest for his own band. When he was 14, Jennings dropped out of school and worked as a cotton picker, until he moved to Lubbock and found a job at radio station KILL.By chance, he met the legendary Buddy Holly, who took the young Jennings under his wing and taught him everything he could about music. Jennings occasionally played with Holly's band, the Crickets, and it was only a last-minute seat-switch with the Big Bopper that kept him off the plane that crashed and ended Holly's career in 1959. After his mentor died, Jennings continued to work as a DJ, until he moved to Phoenix in 1960, and formed his own band, the Waylors. As the band's local following grew slowly, Jennings worked out a deal with the indie Trend label in 1961, although their releases were only modestly received. By 1963, Jennings had moved again, this time to Los Angeles, where he signed his pure country sound with A&M.

Artistic differences with A&M prompted Jennings to sign with RCA and relocate to Nashville, where he moved in with friend and future fellow Highwayman Johnny Cash. Throughout the next several years, Jennings released a series of albums and singles, on which his country sound became more and more pure. Along the way, he teamed up with several musicians, including Kris Kristofferson and Willie Nelson. Those two men, along with Cash and Jennings, teamed up in the 1980s to form the supergroup, the Highwaymen. In the 1990s, Jennings has retained his superstar status and his concerts continue to draw large crowds and positive reviews.

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