This essay considers a tradition of writing and theory that links perversion, utopia, and the philosophical critique of modern forms of rationality. Stimulated by the eighteenth and early nineteenth-century writings of the Marquis de Sade and Charles Fourier, whose works were rediscovered and reinterpreted in the twentieth-century, the Frankfurt School theorists Walter Benjamin, Max Horkheimer, Theodor Adorno, and Herbert Marcuse, as well as the French writers Georges Bataille and Pierre Klossowski, confronted the challenge put forward by Sade’s work, sometimes in tandem with the explicitly utopian writings of Fourier. This essay explores various configurations of perversion, utopia, and the critique of reason these writers advance, and also considers the implicit and explicit theories of perverse/utopian reading these positions adumbrate. I trace a trajectory of mid-twentieth-century debate from positions that at first tend to affirmatively treat the utopian potentials of Sade’s perverse texts, but later seek to sublimate or otherwise redeem perversion from the destructive implications of Sade’s vision. Lastly, extrapolating beyond the immediate textual examples I examine, I view these various thinkers as grappling with the definition of the perverse/utopian text and the relation it establishes with the pleasure of its readers. How, in other words, through an encounter with textual images and narratives of perversion, might readers be hailed into a not yet assembled utopian community of pleasure?