Eric Bentley is arguably one of the most prominent theatre scholar-critics of the twentieth century. He is perhaps best known for translating and advocating for Brecht’s plays in English-speaking countries. In books such as The Playwright as Thinker, he makes the case for non-commercial theatre as a political force and valuable form of cultural expression. In his later career, he turned his attention towards playwriting, which he identifies as his most worthwhile pursuit. His transition from critic to playwright is just one of many major shifts in his life and career, which I argue is defined by doubleness. Bentley even describes himself as living several double lives. These shifts involve politics, sexuality, culture, and artistic expression. In this study, I analyze various writings from throughout Bentley’s career in order to examine the sociopolitical energies at play in his work. Early in this study, I establish post-structural analysis as my overarching theoretical frame. I specifically employ the writings and theories of Michael Foucault, Stephen Greenblatt and the new historicists. Leftist politics and Marxism provide another broad arc to my study of Bentley’s work. My theoretical approach allows me to examine his position within a constantly shifting field of power relations as it relates to public and private social, political, cultural, and artistic issues. Specifically, I look at the circular effects of the relations between Bentley and socialism, anticommunism, the New Left, the counterculture movement, and gay liberation. Throughout my analysis, I view artistic and social performance as a vital cultural expression and a valuable way of exercising power. I look to the House Un-American Activities Committee hearings, Vietnam War protests, the Radical Theatre Movement, and gay liberation as examples of how performance was at the foundation of various major social and political conflicts during the twentieth century. I believe that Bentley was very much aware of performance’s role in these struggles and actively used his capacities as critic, playwright, and public intellectual to draw attention to this, despite his tendency to be caught between opposing sides.