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While we call them games without much critical reflection, this essay asks how well computer and video games fit into usual understandings of the conceptual and cultural functions of play. In different but related ways, in the writings of both Jacques Derrida and Roger Caillois, play is characterized by a certain kind of rule—a rule that is only quasi-teleological and partially breakable, and is fundamental precisely because of its disconnection from particular cultural contexts. Looking closely at World of Warcraft , and in particular the forms of questing, character development, progress, and sociality developed in the game, questions emerge about the degree to which using the game is or is not a form of play. While often discussed as benefits of contemporary gaming environments, the many connections between games like World of Warcraft and external world contexts (historical, political, and cultural), when joined to the game’s problematic instantiation of play, thus can be seen to lead to deep questions about the game’s cultural and subjective functions.