The Diggers, a subversive subset of the broader American counterculture in San Francisco in the 1960s, stood for a unique form of anarchist theater. They presented a form of performance art they referred to as life-acting the game of freedom which was itself a form of what they dubbed guerrilla theater. Drawing on Hakim Bey’s concept of the temporary autonomous zone, Mikhail Bakhtin’s notion of the carnivalesque, and Victor Turner’s idea of anti-structure, the essay examines the Diggers as a unique element within the American counterculture that deserves a critical reappraisal. Analysis of central Digger events and projects provides a view of their distinct perspective, one that critically engages with the politically motivated New Left (including the antiwar and Berkeley Free Speech movements) and spiritually motivated hippies (including unofficial leaders like Timothy Leary). The tactics of guerrilla theater were meant to reveal the contingency of social roles and encourage an anarchistic form of individual responsibility. Digger events provide strategies for subverting normative social structures while providing spaces for the exploration of alternate identities and community structures.