This thesis examines Hamlet and Measure for Measure as related “problem plays.” In these plays, Shakespeare uniquely combines the genre of parable and the literary device of irony as a means to involve his audience in the experience of ordeal and deliverance that both reorients the protagonists’ personal, political, and ultimately theological assumptions and prompts spiritual insight in the spectator. As in a parable, a spiritual dimension opens subtly alongside each story to inform the play’s action and engage the spectator in the underlying theological discourse. Irony invites the audience to see the disparity between pretended or mistaken reality and the spiritual truth—between what “seems” and what “is.” As these complex dramatized parables unfold, potent tapestries of multilayered thematic irony coalesce into providential irony that exalts, rather than defeats, the protagonists and ultimately determines the outcome.