This chapter investigates a cluster of myths relating to androgyny, a mythical structure which is constructed by Ovid's narrative strategies and which informs some aspects of Renaissance literature and art. It proposes the hypothesis that, given the literary and pictorial nature of material under study, two levels of analysis combine, where the human mind thinks itself in myths it generates and where art thinks itself in myths it represents. Paul Barolsky has shown how Renaissance art and art theory plunge their roots in Ovidianism, from which they inherited a spirit of play, the very play of imagination as it gave birth to protean forms of art. The androgyny at work in Michelangelo's and Leonardo's artistic production can be accounted for the context of a Neoplatonician intellectual milieu. Ovid's mythical structure of androgyny, when reassessed through the visual arts of the Renaissance, opens up a whole range of erotic potentialities through which notions of instability and ongoing transformation are addressed.