Two separate and seemingly unrelated myths of Hercules flourished in Rome during the Augustan period: the triumphant Hercules’ defeat of the robber-monster Cacus, and the cross-dressed Hercules’ enslavement to the Lydian Omphale. The question that this dissertation therefore asks is: why did the Augustan period need not simply one, but two Hercules? Traditional scholarly explanations tie the two myths into post-Actium political propaganda: the Hercules who vanquishes Cacus represents Augustus, while the Hercules in thrall to Omphale represents Antony. Loar argues instead that the myths address more broadly two separate anxieties about faltering normative power structures in Rome at the end of the first century BCE. The myth of Hercules and Cacus speaks to concerns about political succession and transition, specifically how Augustus and Augustus’ Rome fit within the narrative of Roman history. The myth of Hercules and Omphale, on the other hand, answers a growing fear about the status of Roman masculinity in an era that is witnessing the rise of powerful women at home and abroad.