Written as a fictitious dialogue between two of this generation’s most prolific social theorists, this unique analysis explores the similarities and divergences of Michel Foucault’s and Yannick Ripa’s scholarship on madness. During an imagined meeting at a local café, a spirited dialogue emerges addressing mutual agreement and unwavering criticism of each author’s perspective of how madness was constructed and managed throughout the classical and Victorian eras. Ripa’s primary motive is to challenge Foucault for ignoring the feminine critique within his over-arching theories of social and patriarchal systems of control. On the other hand, Foucault’s vested interest is to explore Ripa’s narrowed historical scope that he feels was essentially built upon his own scholarship without acknowledgement. Drawing upon a comparative study of Foucault’s History of Madness and Ripa’s Women and Madness, the two theorists engage in a revealing conversation about aspects of political economy, shifting roles of religious ideology, gender effects, the social construction of insanity, and the historical methods of incarceration.