In this article, we explore the presentation and contestation of discourses of womanhood in verbal art performance. In Tuscan-Italian Contrasto verbal duels the artists, both males and females, may impersonate female characters as they exchange insults between each other. In doing so, they deploy multiple discourses of womanhood to demonstrate their wit and verbal artistry. As a consequence, they often subvert and contest “appropriate” female behavior as well as ideas of morality, which might be connected to those behaviors. This highlights the manipulability of discourses of womanhood to obtain particular goals. We analyze Contrasti performances where characters of mother-in-law and daughter-in- law are impersonated. We further argue that the contraposition of different discourses on stage increases the fluidity of gender as a category. In this sense poetic performances are revealed as a loci where perceptions of established gender roles and the connected moral order might be negotiated or destabilized.