This introductory chapter situates the Classical within Foucault’s philosophical work and summarizes the complex reaction of Classical scholars to Foucault’s work. To do so, it considers the issue of freedom of the self in society as explored by Foucault. This issue is, we suggest, the axis around which the Classical works operate: we argue that Foucault’s Classical turn was an encounter with the problematics and possibilities of freedom for and in the self. The possibility of discovering in the antique (and especially the Roman) not just a philosophy of freedom but a praxis of freedom that might be reformulated within the modern gives political and philosophical importance to Foucault’s Rome. Consequently, and as a first step in assessing the viability of Foucault’s project, it becomes crucial to understand whether these ethical practices could provide a measure of freedom in Imperial Rome itself, and secondarily, whether those ethics are desirable modes for modern life.