The emergence of interactive technologies has profoundly altered our relationship to media and art from the position of spectators to that of players. For longer than we might imagine, cultural theorists have foreseen these shifts, feared them, fought for them, celebrated them, and, clearly, misunderstood them. In this course, we will explore the thread of interactivity in cultural media as well as the opportunities and perils posed by the associated rise of mass interpretation, playfulness, and bottom-up organization. We will trace the interactive imperative, from animated cave paintings and the alphabet to cut-and-paste novels and open source programming. We will encounter literary perspectives from Roland Barthes to William Burroughs, media theory from Walter Ong to Neal Stephenson, social critique from Spinoza to Focault, cultural programming from Aleister Crowley to RU Sirius, and play theory from Huizinga to Howard Rheingold, all in the context of the relationship of interactivity to autonomy, agency, and play.