This paper discusses the reception of Ovid’s Metamorphoses through the lens of contra naturam (or actions “against nature”) focusing on two case studies: Titian’s Venus and Adonis and Cellini’s Perseus and Medusa. It exposes the intricacies of gender within Ovid’s Metamorphoses through the lens of sixteenth century Renaissance artists. On the surface, Venus and Adonis is presented as nature taking its course, rectifying the unnaturalness of Venus and Adonis’ relationship, however, further analysis highlights the intricacies between Ovid’s myths and the artist’s intentions through their instability of gender. Similarly, the hero and villain paradigm in Cellini’s Perseus and Medusa is complicated by the nuances of the gendered power dynamics.