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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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Jessi Colter
Jessi Colter was the only woman featured on the landmark 1976 compilation album Wanted! The Outlaws, giving her a foundational role in outlaw country's formal commercial establishment as the genre's most significant early female representative. Her 1975 song "I'm Not Lisa" became a number-one country hit and a top-five pop crossover success, establishing Colter as a significant commercial success in her own right beyond her marriage to fellow outlaw country pioneer Waylon Jennings. Colter's more introspective, ethereal vocal and songwriting style distinguished her from the more overtly rebellious, hard-living outlaw persona associated with many of her male outlaw country contemporaries, giving the movement a genuinely different stylistic register within its broader commercial identity. Her combination of genuine chart success and her foundational role as the outlaw country movement's most significant female artist has made Colter one of the most historically important women in the development of country music's broader outlaw tradition.
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