This dissertation examines aesthetic strategies and conceptions of the individual’s role in society as they can be observed in a specific group of theater plays by German-speaking dramatist Peter Weiss, written between 1964 and 1971. After having been forced to emigrate to Sweden in 1938 (his father was Jewish), Weiss in this period not only thought intensely about the interrelation between individual biography and socio-political reality from a position at the margins of “German” literature and of Germany, but explored how literature and visual art might provide the individual a space to re-identify and affirm subjectivity and, at the same time, to connect with and negotiate social demands. This complex of questions stands at the center of the 1965 Lessing Prize acceptance speech, where Weiss re-interpreted the antique group sculpture which already served as point of departure for Lessing’s text as allegory of a survivor of the Shoah. Marat/Sade (1964) and Hölderlin (1971) mark the beginning and end point of this period. Both plays share a structural similarity through their focus on a historical individual from a period of social change; whereas the latter takes as starting point the poet Friedrich Hölderlin’s literary writing, the former emanates from the visual depiction of the death of Jacobin politician Jean-Paul Marat by painter Jacques-Louis David in La Mort de Marat (1793), adding as counterpart to the protagonist his contemporary, the writer Marquis de Sade. Analyzing these plays 1) in close readings, 2) against the backdrop of theories of the image and of deixis, and 3) with a particular focus on moments that probe the relation between text and image, I suggest that Weiss’ conception of the biographical drama allows for two simultaneous and related discourses: one about the potential and limits of language and image to adequately represent reality, and the other about the individual’s challenge to reflect (on) its proper subjectivity while negotiating his or her place in so-called reality.