Taking its direction from seminal works in the field of play theory, this dissertation examines ludic elements in the textual practices and intellectual community of the Union of Real Art (Ob”edinenie real’nogo iskusstva or OBeRIu). I use the concept of play to elucidate how the group used literature as an unconventional medium for the pursuit of special forms of knowledge and to explore the intimate genre of performance that shaped the association’s collective identity as a group of writers and thinkers. The four chapters that comprise this dissertation each examine one facet of how play shaped the OBeRIu’s shared literary practice. In the first chapter, I contrast the performative strategies of the OBeRIu members (or the oberiuty) with those of the Russian Futurists, demonstrating that the OBeRIu approach to spectacle possesses an ‘existential’ dimension that is quite alien to that of Futurism. I argue that Futurist performance is best characterized by what Hans-Georg Gadamer has called “aesthetic differentiation,” a hermeneutic tradition that foregrounds the autonomy of the artwork while ignoring its rootedness in broader spheres of cultural activity. In contrast, the members of the OBeRIu (the oberiuty), were engaged in what some theorists have called deep play: they showed little interest in the épatage tradition practices by the Futurists and drew no meaningful distinction between art and life.I suggest that performative strategies of the oberiuty can be productively interpreted according to Gadamer’s concept of “self-presentation,” a notion that proves immensely useful for understanding not only the group’s theater, but their written work as well. In my second chapter, I show how the OBeRIu’s playful approach to writing was underscored by their commitment to an epistemic understanding of literature: they believed that literary pursuits constitute a unique form of knowledge. I suggest that the texts produced by the oberity frustrate the boundary that supposedly distinguishes poetry and philosophy. I demonstrate how even a playfully ‘absurd’ text such as Daniil Kharms’s “Blue Notebook No. 10” can be read as a work of philosophy—in this case as a kind of performative refutation of Kantian metaphysics. I suggest that the epistemic register of OBeRIu literature can be likened to what Roger Caillois has called games of ilinx—their texts induce a kind of cognitive vertigo that pushes readers towards forms of knowledge that cannot be properly conceptualized. As a form of epistemic play, OBeRIu texts open onto the world even as they exist ‘beyond’ it, inviting readers to appreciate in poetry what Gadamer called “the joy of knowledge.” In the third chapter of this dissertation I argue that the commitment of the oberiuty to an epistemic understanding of literary art places them squarely at odds with premises fundamental to the theories of Russian Formalism. Indeed, I demonstrate how the OBeRIu as a group deliberately problematize the Formalist concept of literariness. I demonstrate that the poetic episteme of the group took direction from Russian Orthodox theology, particularly the concept of the eikon. The epistemic nature of OBeRIu ‘nonsense’ precludes interpreting their texts as exercises in Shklovskian estrangement. Instead, I suggest that Gadamer’s notion of recognition is invaluable for understanding the work of the oberiuty. Their literary work articulates something and in doing so adds to our understanding of the world. In the final chapter I consider the community of chinari, which constituted a kind of intimate ‘inner circle’ for the OBeRIu that was both more private and longer lived than the Union of Real Art itself. I suggest that the chinari circle can be understood as part of a discernible line of extra-institutional play communities in the history of Russian letters that began with the Arzamas Society of Obscure People. I argue that play was the raison d’être of the chinari community and largely defined the sense they had of themselves as an intellectual community. Considering closely Leonid Lipavsky’s Conversations, a more or less authentic record of the group’s discussions between 1933 and 1934, I suggest that the group used the speech genre of bullshit quite productively—it was both a fun way to explore ideas and, more importantly, a phenomenally effective way to foster their collective bond.