In a time exceptionally preoccupied with the relations between the personal and the political, sexuality and power, Measure for Measure is one of the most frequently staged and discussed of Shakespeare’s plays. Drawing on performance history and current critical approaches, this study considers the play in relation to its historical contexts and contemporary relevance. It traces the dramatic unfolding of the plot through the social and theatrical spaces of Shakespeare’s Vienna: court, convent, prison, and public street. It explores the intertwining of religion, sexuality, politics and morality in the institutions associated with the maintenance of social order in Vienna, and asks whether the world of the play holds open any possibilities for challenging the power of these institutions. The reader is led carefully through some of Measure for Measure’s most problematic moments, but the compelling theatrical pleasures offered by this strange and fascinating play are not overlooked.