This essay develops an understated argument in Stuart Scheingold's The Political Novel (2010), namely, how narratives of estrangement serve to empower re-imagination without reinforcing the false promises of modernism. I argue that Scheingold's earlier work in The Politics of Rights and on cause lawyering provides guidance for understanding the character of empowerment to which Scheingold points in his latest work. In addition, I examine three film narratives that treat the “mournful legacy of the twentieth century”—Pan's Labyrinth, Life Is Beautiful, and Everything Is Illuminated. Emergent in these narratives, I suggest, is a way that storytellers point to empowerment by highlighting the largely overwhelming constraints that limit the agency promised by modernism and the strategic, though contingent, choices characters make to confront and cope with their own estrangement.