This chapter examines Gil Scott-Heron as an exemplar of the socio-political manifestation of the contrarianism in funk aesthetics. Combining biographical information from Scott-Heron’s memoir and interviews, critical methods from literary scholarship, and insights from philosophy, the chapter highlights Scott-Heron’s understanding of the blues as a locus of black aesthetics and political philosophy. In doing so, the chapter illuminates Scott-Heron’s prescience, and examines many of his multiple talents, including poetry, songwriting, singing, and playing keyboards. Unlike most recording artists, however, Scott-Heron was influenced by writers, especially the Black Arts writers who generally believed that artists should create primarily for working-class African Americans. Consequently, he curtailed his budding career as a novelist and shifted his concentration to performing and recording songs and poems in the early 1970s. The chapter includes textual analyses of key recordings as well as discussions of Scott-Heron’s satire and social criticism. Additionally, Bolden highlights musical aspects of Scott-Heron’s appeal, especially the timbre of his voice but also the musicianship of the Midnight Band, which he co-led with longtime collaborator Brian Jackson.