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Kris Kristofferson
Kris Kristofferson, a Rhodes Scholar and former US Army helicopter pilot before turning to songwriting, brought an unusually literary sophistication to country songwriting, and his songs "Me and Bobby McGee" and "Help Me Make It Through the Night" became major hits for other artists before Kristofferson established his own recording career. His decision to abandon a stable military career and enroll as a janitor at a Nashville recording studio specifically to be near working songwriters reflected an unusually deliberate and risky commitment to pursuing songwriting professionally, a choice that initially alarmed his more conventionally successful military family. Kristofferson's willingness to address themes of drug use, sexuality, and personal disillusionment with unusual directness for country music of his era gave his songwriting a more literary, less conventionally moralistic perspective than much of mainstream Nashville country at the time. His combination of genuinely sophisticated literary songwriting and his significant catalog of songs later popularized by other major artists has made Kristofferson one of the most critically respected songwriters within the broader outlaw country movement, even relative to his own more modest commercial success as a performer.
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Waylon Jennings
Waylon Jennings was originally scheduled to fly on the small plane that crashed in 1959 and killed Buddy Holly, Ritchie Valens, and the Big Bopper, but Jennings gave up his seat to the Big Bopper, who was ill, a decision that haunted Jennings for the rest of his life and became one of the most significant near-misses in rock and roll history. His 1976 compilation album Wanted! The Outlaws, featuring Jennings alongside Willie Nelson, Jessi Colter, and Tompall Glaser, became the first country album certified platinum and helped formally establish "outlaw country" as a recognized commercial genre distinct from mainstream Nashville production. Jennings's insistence on creative control over his own recordings, rejecting Nashville's typically producer-driven studio system in favor of using his own touring band and choosing his own material, became a defining principle of the outlaw country movement's broader rebellion against the industry's established conventions. His combination of genuine creative independence from Nashville's studio system and his central role in outlaw country's commercial breakthrough has made Jennings one of the most historically foundational figures in the genre's development as a recognized commercial and artistic movement.
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