This chapter offers a thorough analysis of both the literary tropes surrounding tyranny and the tyrant in fifth-century Greek literature—with some reference to fourth-century and later texts—and the function they played in democratic self-understanding. The chapter addresses the ongoing debate about the existence of a democratic theory of democracy in fifth- and fourth-century Athens, arguing that a proper democratic theory did not exist. Within the context of this debate, the chapter draws on theses of Diego Lanza, Giovanni Giorgini, and James F. McGlew that the depictions of tyranny in anti-tyrannical literature served the purpose of offering to the democratic citizen an inverted mirror with which he could contemplate the key features of democratic practice, by way of opposition. In other words, hatred for a highly stylized discursive representation of tyranny played a key role in democratic self-understanding.