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Billy Joe Shaver
Billy Joe Shaver wrote nearly the entirety of Waylon Jennings's influential 1973 album Honky Tonk Heroes, a record widely credited as one of the foundational albums of the outlaw country movement, giving Shaver significant behind-the-scenes creative importance to the genre's earliest commercial breakthrough. His own recording career, while never achieving the same commercial success as Jennings or Willie Nelson, earned him deep respect within the country music songwriting community for the raw, autobiographical honesty of his lyrics, drawing directly on his own hardscrabble Texas upbringing. Shaver survived a serious heart attack and open-heart surgery in the mid-2000s, and a 2007 shooting incident in which he shot a man in self-defense outside a Texas bar, for which he was later acquitted, added to his genuine outlaw reputation well into his later life. His combination of foundational songwriting contributions to outlaw country's earliest landmark recordings and his own uncompromising, autobiographically honest performing career has made Shaver one of the most respected "songwriter's songwriter" figures within the outlaw country tradition.
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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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