John Webster’s The Duchess of Malfi, one of the most prominent examples of revenge tragedy in the English Renaissance, presents the complex character of Bosola in a manner that distinguishes him from conventional villains. This study therefore proposes a model that moves beyond classical definitions of villainy: an individual who, while outwardly conforming to the aristocratic order, simultaneously engages in a concealed struggle against its dominant values. In contrast, the contemporary Iranian adaptation of the play by Naghmeh Samini and Mohammad Rezaei‑Rad reimagines Bosola as a “mad hero” who transcends structures of power and rebels against systemic corruption. In discussing this figure of the mad hero, it is necessary to refer to the prior concept of the “mad villain,” since the two are intrinsically interdependent. The mad villain stands beyond the will to power, finding both power and submission equally insignificant; his actions acquire an absurd dimension, as though he were laughing in the face of the world itself. The mad hero, up to a critical turning point, remains that very villain; yet after encountering a transformative element and subsequently losing it, he adopts a destructive behavioral constellation whose outcome is the annihilation of both the self and the agent responsible for the erasure of meaning. He thus comes to perceive himself as bearing a mission to eliminate forces that disrupt established values. Drawing upon Chekhov’s theories of theatre psychology, Baudrillard’s philosophy of evil, and Lyotard’s reflections on the collapse of morality, this research conducts a comparative analysis of the two representations of Bosola across four dimensions—psychological, philosophical, social, and political—and investigates the process of his transformation. The central question concerns the psychological mechanisms and surrounding consciousness that enable this shift from “mad villainy” to a self‑aware “mad heroism.” The findings indicate that, in the Iranian interpretation, villainy is redefined as an instrument of rebellion against a greater evil, while madness becomes a liberating and agentive force. Bosola is the only character capable of confronting the Cardinal, for “no hero is as capable of stopping a villain as another villain,” and he ultimately pursues the Duchess’s vengeance along with that of the other victims. This transformation—psychological, ethical, and socio‑political in scope—reflects contemporary crises and demonstrates the capacity of dramatic literature to engage critically with them.