Transgression - understood as the crossing of normatively set boundaries of knowledge, experience, and identity - has been both a motive and a method in subversive art and critical cultural analysis since the Enlightenment. Using the example of the writer Kathy Acker, Florian Zappe's study, situated in the interdisciplinary borderland between literary studies, cultural studies, and philosophy, reflects on the possibilities of radical art as a medium of cultural criticism, while also providing a cultural history of the concept of transgression in modern and postmodern avant-gardes.