This dissertation examines the relationship between democracy and autocracy in the political imagination of fifth-century Athens through an analysis of the figure of the tyrant in Athenian tragedy. To probe this question, I conduct close readings of Sophocles’ and Euripides’ tragedies, including fragmentary plays. By also engaging with literary and material evidence outside of tragedy, I put the plays in conversation with the broader socio-political discourse of Athens to reconstruct the Athenian democratic ideology of tyranny. I employ a notion of “ideology” as not merely equivalent to “normative discourse”, but as including both democratic norms and their transgressions. This research shows that tragedy exploited and heightened the Athenians’ ideological ambivalence toward tyranny as it depicted the tyrant as an ambiguous character, which directly contrasted with the hatred for tyranny the city promoted in more official contexts such as democratic assemblies. Dramas often evoke sympathy for tyrannical figures through the blurring of the distinction between tyrannical and democratic behavior. Tragedy allows the democratic citizen to vicariously enjoy the tyrant and his power, even if it also reminds the spectator of the tyrant’s own failure and the danger he represents for the democratic community. This study contributes not only to our understanding of the ideological function of tragedy in democratic Athens but to a more comprehensive assessment of the role of tyranny within Athenian democracy, offering a nuanced exploration of the tensions between democratic ideals and less sanctioned tendencies within the city. This research prompts us to consider whether such sentiments can be connected to Athens’ emergence as a hegemonic power in Greece in the course of the fifth century. It also encourages us to ask whether such anti-democratic feelings have an element of universality, suggesting parallels between ancient Athens and contemporary democracies witnessing the resurgence of autocratic practices as well as democratic skepticism.