This article tracks various twentieth-century figural appropriations—in the realm of artistic theory and practice—of a controversial method of treating the mentally ill. In the first section, I revisit Walter Benjamin’s canonical speculation on the importance of a shock aesthetic, underscoring the functional imperatives informing his model. For him, shock was the aesthetic cornerstone of cultural undertakings designed to enable persons to inhabit urban-industrial modernity in a socially empowered fashion. In the second section, I apply this notion to two products of the American underground: Marie Menken’s Go! Go! Go! (1962–1964) and Jonas Mekas’s Walden (1969). Here, my argument is that it was in experimental film that the purposefulness or “mission” that Benjamin detected in Charles Baudelaire’s poetry was realized. I then conclude with some reflections on the pertinence of the model in question to two related avant-garde cinematic endeavors: Stan Vanderbeek’s collage works and Ken Jacobs’s Nervous System performances.