This chapter argues that a theological lens allows us to see Shakespeare’s comedies as radical experiments with grace, rather than as the displays of social conservativism they are often taken to be. Anarchy reigns in these plays: within language, within genders and ontologies, and at times even within the script itself. In short, nothing is stable, and this seems to call into question any sort of supernatural care for the structure of the world. When the “grace” of meetings, reconciliations, and unveilings finally occurs, it is not through the orchestration of any planner of events, but rather through the wits of adaptive characters like The Merchant of Venice’s Portia, As You Like It’s Rosalind, or Twelfth Night’s Viola. Unlike the Iagoan wit, though, these comic heroines understand their “intellectual humor” to be a repetition of a wittiness that exceeds their control: theirs is a participatory wit. Finally, the chapter considers Much Ado about Nothing’s Dogberry, whose dialogue maintains an unresolved anarchy that leads to the surprise of truth, making him an accidental means of grace.