With a career that lasted half a century and spawned no less than 16 number one singles, few artists have had as important an impact on modern country music as Waylon Jennings. Born in Littlefield, Texas, Jennings dropped out of high school to become a DJ at the age of 15. He moved to Lubbock and became close friends with Buddy Holly, who was also his musical mentor. Holly taught Jennings how to play guitar and bass, and encouraged him to become a writer and singer. Jennings left radio to record for Brunswick Records in 1957, with his first record produced by Holly himself. When Holly needed a new bass player for the Crickets in 1959, he called Jennings, who took the gig. On February 3rd, Jennings gave up his seat on a small private plane that was scheduled to carry himself, Holly, and Ritchie Valens to the next gig. The other star on the tour, the Big Bopper, had the flu, so Jennings infamously let him take his seat on the four-seater plane, which ended up crashing and tragically killing all three stars.
Jennings re-emerged in the 1960s as a country star with the help of Chet Atkins, who signed him to RCA Records, where he would remain for over a decade. He relocated to Nashville during an era of rather strict corporate policies, but determined to have his creative freedom, he began broadening the scope of country music by embracing elements of rock music and using his road band in the studio, both highly discouraged practices in Nashville at the time. This rebellion against Nashville corporate traditions and production formulas (in addition to his well publicized embracement of illegal substances and battles with addiction) became a critical aspect in the development of his "outlaw country" persona. It was Jennings determination to have complete artistic freedom that was also embraced by friends and musical collaborators such as Willie Nelson, Johnny Cash, Kris Kristofferson and Merle Haggard that established the "outlaw country" genre. In time this would have a profound impact on subsequent generations of country songwriters and musicians, creating a new blueprint for much of modern country today.