This dissertation explores how, in their attempts to explain the transformation of cultural forms across different media, certain theorists, artists, and authors have turned to the models, metaphors, images, and narrative structures of biological evolution and (post-)Darwinian theory. It argues that, in so doing, they have often tended to reveal their own anxieties concerning the status of art and human beings (typically men), rather than provide a so-called objective model for explaining cultural change.Through an interdisciplinary study of the theoretical and cultural inheritance of Darwinism in the fields of “adaptation studies,” “transmedia studies,” and “biocultural studies,” this dissertation assesses how evolution and its offshoots have been put to work by theorists and artists who have created, studied, and consumed works of art that blend and mix media, hybridize forms, and probe the limits of cultural adaptation, evolution, and transformation. Tracing the variously explicit or implicit deployments of evolutionary ideas in the production and theorization of culture generally and adaptation specifically, the dissertation reveals ongoing anxieties about human and non-human sexuality and procreativity, the separation of nature and culture, the biologically or culturally determined differentiation of sexes and genders, the value of art within utilitarian frameworks, and the reproduction of artworks and organisms in a heteronormalized bioeconomy. Beginning with an overview of the reception of Darwinism and the overlapping discourses concerning media adaptation in culture and biological adaptation in nature, the dissertation’s introduction assesses how certain paradigms and assumptions of evolutionary science have filtered into the discipline of adaptation studies. The first chapter then offers a rereading of a key film within that field, Adaptation (2002), written by Charlie Kaufman and directed by Spike Jonze, historicizing its evolutionary paradigms. Subsequently, chapters on the transmedia aesthetics of Marcel Proust, Vladimir Nabokov, and Peter Greenaway assess the uses to which evolutionary theory has been put in works that combine and transform multiple media forms. By identifying a recurrent set of anxieties across these works, many of which insist on particular gender hierarchies and reproductive essentialisms, the study attempts to offer a historically alert assessment of biological and cultural adaptation after Darwin.