This dissertation considers concepts of play in literary texts by four German writers of the long nineteenth century: Johann Wolfgang von Goethe, Clemens Brentano, E.T.A. Hoffmann, and Franz Kafka. Unlike previous studies which have focused on play in individual writers or texts, this study identifies a historical trajectory (resonance) of play in canonical writers where agency steadily decline with the possibility of play for the individuals represented in their texts, and its consequences. Taking inspiration from the psychoanalytic approach to play of Donald Winnicott, and the anthropological approaches of Friedrich Schiller and Johan Huizinga, I argue that play can be identified in the representation of self-development (Bildung) in Goethe's oeuvre, as representative of the Romantic self and imagination in two texts from 1816/7, and in the deadly machinations of the state in Kafka, as well as his characters' attempts to resist this. Play is more than a symbol of linear psychological development or an action children do; it can describe a whole attitude, especially in how protagonists 'play by the rules' of texts or treat objects in them as playthings for their own ends. Play is ultimately representative of the status of agency in different ways in these four writers, with Goethe developing a sovereign notion of Spiel which I trace back to the influence of Shakespeare and Machiavelli. Brentano and Hoffmann's fairy tales deliberately question concepts of identity using play objects such as books and dolls and near-human robots. Kafka identifies Spiel both in the machine of the state and in the repeated small movements his protagonists make to try to elude it. In establishing a new framework for the study of play in literature as focusing on objects, not only in a psychoanalytic sense but also a structural one; on identity, in the sense of play as representing values and rules in a text, and relating it to interdisciplinary theories of play, my thesis contributes to the fields of Play Studies, Goethe Studies, German Romanticism, and Kafka Studies in offering this new theoretical approach.