This study makes an attempt to analyze the manifold aspects of Shaw's "Androcles and the Lion" on a postmodernist standpoint, meanwhile, demonstrates the dominion of modernism, which is portrayed through the vehicle of comedy with a bitter ironic language through the play. Regardless of the historical period in which the play occurs, the term postmodernism with its lineaments can aptly scrutinize the clash between modernism and postmodernism, and define the notion of freedom in a world where man is in fetters, either physically or mentally or both at the same time. This study tries to show how two Christian prisoners find their way to freedom by resisting against the suppression and oppression of an empire, whose glory rests on silencing the opposing voices.