This essay analyses the particular appeal of Kleist's work for the filmmakers of the New German Cinema movement in the Federal Republic during the late 1960s and early 1970s. Both Volker Schlöndorff's Kohlhaas – der Rebell (1968) and Hans-Jürgen Syberberg's San Domingo (1970) invite the spectator to view the student movement and the political events of 1968 through the prism of Kleist's Michael Kohlhaas and Die Verlobung in St. Domingo. Although Schlöndorff's film attempts to launch a radical critique of Kohlhaas's individualistic quest, the reluctance to abandon an essentially conservative aesthetic is at odds with Schlöndorff's quasi-Marxist reading of Kleist's novella. By contrast, the avant-garde aesthetic of Syberberg's San Domingo represents an attempt to develop a visual correlate to the distinctive character of Kleist's prose fiction generally, and of his radical treatment of the San Domingan uprising in particular. While San Domingo portrays the rise of such marginalised groups as the Rockers from Am Harras as a logical consequence of an increasing process of alienation from capitalist society, it also articulates a critique of left-wing sentimentality in its portrayal of the central protagonist, Michael König.