While many rock artists explored the compositional possibilities of the concept album in the 1960s and 1970s, Nashville's country music community largely ignored the format. But a few artists working on the fringes of country music – and who, notably, aligned themselves with the countercultural images and attitudes of the time – did begin to experiment with the format in the first years of the 1970s. Chief among them was country songwriter and recording artist Willie Nelson who, by the dawn of the 1970s, was on the verge of breaking away from Music Row to seek more lucrative opportunities in Texas. This article explores the role that Nelson's experimentation with the concept album played in his efforts to adopt a countercultural image, develop a younger audience and challenge the hegemony of the country music industry. Moreover, close examination of Nelson's compositional approach to three albums – Yesterday's Wine (1971), Phases and Stages (1974) and Red Headed Stranger (1975) – reveals that Nelson consciously blended the singles-based approach to songwriting that predominated in 1960s and 1970s Nashville and the extended narrative and musical forms of contemporaneous rock music to create musical products that suited the needs of country radio and rock fans alike.