Geoffrey Chaucer’s medieval, fictitious wife of Bath rekindled the debate about women who were forced to live by their hymen as virgin brides before marriage or as sequestered nuns. Both options precluded sexual pleasure and forced female existence into narrow, male-dominated social parameters. Excluded from the economic arena, medieval women were relegated to a subservient existence within the home. In the form of Alison, the wife of Bath, Chaucer presents a radically different role model for women that breaks out of medieval conventions. The video artist Madonna Ciccone pushed social and biological concepts related to virginity even further by redefining male-based linguistic signifiers, such as “virgin” and “whore.” Through a cleverly arranged visual text, she slips away from male focused sexuality into her own postmodern, autoerotic self-fulfillment. This study will focus on two different representations of female identities outside of hegemonic norms: Geoffrey Chaucer’s “Wife of Bath” and the artist Madonna.. Keywords: Gender Studies, Popular Culture, Feminist Theory, Women’s Studies, Medieval Studies.