At first glance, the fact that the English word for drama is “play” must strike the modern reader as odd. Playing is usually an activity we associate with games (or musical instruments), yet this odd linguistic trace is a forgotten marker of how far the modern sense of drama has strayed from its antecedents. This dissertation recovers the historical relationship of drama, play, and games, developing a shared discourse under the rubric of “play studies.” Play is defined in two complementary phenomenological frameworks, methexis and mimesis, to enable scholarship that transcends historical, cultural, and material boundaries. The first chapter engages the linguistic confusion surrounding late medieval drama (with examples from Mankind, cycle plays, and Fulgens and Lucres) and medieval games (The Game and Playe of the Chesse, The Book of Games), arguing that the medieval English view of play can help correct and complicate modern game scholarship. The second chapter takes up this medieval perspective of play-as-methexis and demonstrates its applicability to digital media of the late 20th century with examples from video games like Tetris and Dragon’s Lair. Along the way, this chapter also makes ontological arguments in relation to early computer history, software studies, and media archaeology, advocating that a fuller understanding of games depends on the willingness of humanities scholars to build, hack, and play with media using methods normally reserved for artists and scientists. The final chapter considers the lasting legacy of the medieval play-as-game, particularly how the development of English drama is indebted to the theater buildings that created a space for the sustained collaboration of players with a variety of skills. The final section considers the current state of Shakespeare-as-play, including 21st-century productions, digital video games, and board games.