This essay traces the significance of Maya Deren in Annette Michelson’s thinking about what she termed film’s “radical aspiration.” Deren offers Michelson a number of appealing coordinates that mirror, to some extent, Michelson’s own biography and intellectual interests: Deren’s formation included attachments to both socialist politics and Anglo-American high modernism; she embraced ethnographic theory and research; she had an interest in modern choreography. Perhaps most important for Michelson was Deren’s status as filmmaker and theorist. This distinction was one she shared with other figures also important to Michelson, chief among them Sergei Eisenstein and Stan Brakhage. In fact, Deren frequently appears (or seemingly can appear) in much of Michelson’s writing only insofar as she mediates the distance between the Soviet montage artist and the American romantic experimentalist. Michelson’s ambivalent emphasis on Deren as a specifically “woman artist” also points to Michelson’s ambivalent relationship to second-wave feminism, which was itself the context for the renewal of interest in Deren’s work among feminist film theorists and historians in the 1970s. I argue that Deren provided Michelson an appealing matrix in which the full range of Michelson’s interests, commitments, and ambivalences can be seen in productive tension with one another. Deren occupied an essential marginality in Michelson’s thinking about the possibilities and the vicissitudes of radical film praxis and theory.