Tolstoy’s relationship with staged art was anxious and passionate. He was not a man of the theater – of the performing arts, music was his passion – and he was highly critical of many playwrights, such as Shakespeare and Chekhov, whom he felt abused the medium. And yet he authored several powerfully effective dramas (comedies and tragedies) as well as numerous experimental dramatized folktales and parables, and even a quasi-fictive version of his own diaries in dramatic form titled A Light Shines in the Darkness. Tolstoy composed theatrical works in two distinct periods, early and late, on either side of his spiritual turning point. This essay discusses the major plays and one exemplary didactic folk miniature (The First Distiller, 1886) in the context of nineteenth-century Russian theatrical resources, official censorship, and Tolstoy’s own evolving sense of theater’s “infectiousness” as an instrument of communication and moral growth, moving from the unsuccessful farce The Infected Family (1863) through The Power of Darkness (1886), The Fruits of Enlightenment (1889), and The Living Corpse (1900). On the stage as in his prose, Tolstoy emerges as a “realist” only in the most superficial sense. In both venues he is a rebel.