Two centuries after Heinrich von Kleist’s death, scholars still contend with the problem of the fantastic in his short stories and dramas. Kleist’s fantastic often takes the form of characters who may or may not possess supernatural power or manifests during strange events which defy rational explanation. What makes these fantastic elements different from those found in works more widely considered to belong to the fantastic genre is their eruption into seemingly ordinary fictional worlds. More precisely, these instances of the fantastic contradict the rules of the fictional worlds they interrupt and cast doubt on the version of reality perceived by the characters. Though Kleist certainly transgresses the boundaries of reality in multiple works, the method and meaning behind these fantastic elements often remains ignored or misunderstood. Scholars widely accept that Kleist’s fantastic differs from that of other authors, but the precise differences that set Kleist apart have not been extensively investigated. This does not mean that the question of reality in Kleist’s works has been ignored. Recent Kleist scholarship has tended to focus on Kleist’s manipulations of reality rather than address the structural question of genre. Carol Jacobs’s “The Style of Kleist” and Nancy Nobile’s “‘Sein Nahen ist ein Wehen aus der Ferne:’ Ottokar’s Leap in Die Familie Schroffenstein” each explore Kleist’s tendency to obscure reality through careful selection and omission of detail. To Jacobs, Kleist wields his style like a scribe wields a stylus for both the creation and erasure of meaning. The author’s tendency to create diversions or omit detail at critical moments is, Jacobs argues, a conscious stylistic choice. Jacobs investigates Kleist’s obscuring of cause and effect and seeks to understand the role that language plays in these manipulations. Nobile’s piece reconciles the grotesque fifth act of Die Familie Schroffenstein, in which a witch brings about an improbable resolution, with the play as a whole. Nobile argues that the play’s structure reveals an author conscious of the theater’s artifice and willing to expose illusions of reality. The piece does not directly deal with the fantastic, but Nobile goes against the grain of earlier scholars and critics who dismissed or ignored Kleist’s sudden shifts away from the accepted reality of the fictional world. Other recent research has focused on the role in Kleist’s works of such markers of identity as gender, class, and race. These motifs are not the focus of this thesis, but their emergence as areas of interest for Kleist scholars points to a fascination with the way characters fit into the social reality of their fictional world. Stephen Howe’s Kleist and Rousseau presents Kleist as an author who engaged with social and political philosophy. The two categories of research mentioned here represent investigations into Kleist’s manipulation of fictional reality as well as evaluations of identity and social order in his works. This project will unite these two seemingly disparate areas of research by examining interactions between motifs of language and social structure, chiefly family and religion, in order to understand an alternative vision of the fantastic. The Kleist stories examined here, Der Findling, Die heilige Cäcilie, oder die Gewalt der Musik, and Michael Kohlhaas, present families as critical points where socially or culturally imposed structures of reality fail. Der Findling and Die heilige Cäcilie each explicitly challenge constructed families, and in all three stories a preoccupation with blood families and their survival exists against backdrops of widespread spiritual crisis. This paper will examine Kleist’s fantastic with the aid of the definition of the genre provided by Tzvetan Todorov in The Fantastic: A Structural Approach to a Literary Genre. Todorov claims that readers of the fantastic must hesitate alongside the characters between a supernatural and natural explanation of events and reject any allegorical or poetic reading of fantastic occurrences. Todorov’s definition applies more surely to the works of authors like E.T.A. Hoffmann, in which uncanny elements do not enter the text as abruptly or unexpectedly as they do in Kleist’s works. This approach to the fantastic offers a model of the genre as a literary mode which arises out of points of hesitation. Although Todorov’s model falls short when applied to Kleist, its basis in a conflict between two interpretations of reality will serve as a point of departure for this project.