This book offers a protohistory of human-machine relations in literature and philosophy, focused on automata, robots, and the imaginary - and imagery - of animated nonhuman objects. Each chapter offers a distinct historical-philosophical epoch within human-machine thinking, and successively unfolds towards a contemporary theoretical approach to robots as `companion species'. Part One (`Then') explores deep historical connections between particular treatments in literature and philosophy of android (human-like) and zoomorphic (animal-like) machines: from Ovid's Metamorphoses and the poetic imagination of the living statue Galatea, to Descartes' and La Mettrie's mechanical materialism, and the relationship between human movement and machinic production after Marx through such figures as Foucault, Marey, Deleule, and Guery. Part Two (`Now') moves away from the conventional Western approach to lifelike machines as `uncanny' to examine contemporary behavioral ecologies of human and nonhuman machine, and the increasing presence of human-robot interactions within domestic spaces. Donna Haraway's concept of `companion species' is used to help rethink these new ecologies, examining interactions with actual robotic toys and machines, along with representations of such companion robots in `old' and `new' media. Each chapter therefore focusses on typical representations of interactions between humans and machines at a key historical stage in philosophy or literature, and latterly through contemporary film and videogames. The result is an unfolding historical narrative that cumulatively grounds more complex behavioral ecologies of hybrids of machine and organism, that is, bio-social-technical apparatuses that encompass human and nonhuman robots, replicants, and automata. This interdisciplinary volume takes a novel approach across literature, philosophy, and social science, and will appeal to scholars of Animal Studies, Medical Humanities, History of Science, Science and Technology Studies, Posthumanities, Media Studies, English literature, Cultural Studies, and Sociology of Health.