This comparative project investigates different representations of the sandman between the 19th century and the 20th century. My discussion focuses on Romantic texts, in particular E.T.A. Hoffmann's 1816 literary tale "Der Sandmann." While the traditional scholarship on Hoffmann uses both psychoanalytical and feminist approaches, I show how Friedrich Schlegel's concept of chaos and Jean-François Lyotard's concept of the postmodern sublime help us to understand Hoffmann's complex narrative structure. I argue that in Hoffmann's tale there is no unified sandman figure. However, different storytellers in the tale shape the sandman's various depictions. In a way, the sandman figure becomes a fluid character whose enigma the narrative's structure sustains. Paul Berry's 1991 stop-motion animation "The Sandman" visualizes Hoffmann's narrative. However, the film also reintroduces a unified sandman figure that is characterized by uncanny strangeness. My analyses both of Hoffmann's literary and Berry's cinematographic narrative show that their complex structures allow for ceaseless interpretations. This leads me to conclude that fantastic narratives lend themselves to insightful and critical ponderings.