The social and cultural authority that images exercised in medieval Byzantium derived in part from their consistent observance of established traditions of representation. As a result of this tendency toward recognisable types, when an intentional departure from visual conventions was introduced, Byzantine viewers could be expected to notice the difference and wonder about the intentions behind it. This chapter explores how Graeco-Roman mythological and romance narratives offered opportunities for the engineering of amusing imagery through strategies of inversion and exaggeration. It focuses especially on how this up-ending of visual conventions served to disrupt the expected order of gender relations. The chapter shows how the programmes of middle Byzantine works of classicising art used humour initially to destabilize – but ultimately to reaffirm -- social norms surrounding female sexuality.