Tyranny’s lengthy history in European debate lends itself to a linear narrative, and this chapter inserts, into that frame, debates over tyranny from archaic Greece to the contemporary era. Linearity often presents a false picture of continuity, progression and coherence, none of which can be bestowed upon tyranny. Rather, there are controversies and contingencies: the rise and fall of empires, the emergence of the Catholic Church, colonialism, constitutionalism, democracy and individual and collective roles contribute to contemporary tyranny’s complexity. Progressing through a history of Western thought – including its imperialism – highlights how changing attitudes towards governance affected accounts of tyranny. This account reveals how Roman hatred of monarchs, attitudes towards gender, the invention of race, the emergence of contemporary democracy and consequent concerns over majority tyranny demonstrate a consistent concern built into a European tyrannical theory subsequently projected onto the rest of the world.