Parts of the Holy Roman Empire and Central Europe in the Middle Ages seem to have had something of a trope about evil, rapacious prince-bishops abusing the peasantry and getting some karmic comeuppance. I'm thinking particularly of the story of the Mouse-Tower of Bingen, in which a corpulent clerical ruler hoards all his region's food during the Great Famine to secure his own survival, driving away all the people from the land, only to find that his rapacious concentration of vittles has attracted an insatiable mass of rats, who then consume him and his stash. Delightful stuff.

Looking towards England in the same period, there are similar depictions of ecclesiastical malfeasance in Chaucer's Canterbury Tales; specifically in the tales of the Friar, the Summoner, and the Pardoner, who represent various forms of official corruption and moral failing.

The term "tyrant" did not originally have negative connotations when the Greeks borrowed it from the Lydians in the 7th century BC. It simply indicated a person of great wealth and influence, without necessarily implying autocratic rule. However, by the late 6th century the meaning of the word had shifted. The definition of a tyrant was now someone who seized absolute power in a state without regard for that state's laws; they were increasingly stereotyped as violent usurpers, morally corrupt, insatiably greedy, and constantly fearing for their lives due to the threat of assassins and enemies from within and without. Greek communities feared tyranny more than anything, and went to great lengths to prevent tyrants coming to power. Throughout the Classical and Hellenistic period in Greece, we see the rise of the Evil Tyrant trope, with later tradition attaching ever more outrageous anecdotes of paranoia and perversion to the lives of actual historical dictators.

However, tyrants also had a place in Classical Greek thinking about how a state should be governed. While most Greeks abhorred one-man rule, some were in two minds about it, aware of the advantages that absolute power had in terms of the speed of decision-making and the mobilisation of resources. The tyrannies of Peisistratus at Athens and Periander at Corinth were widely regarded as golden ages, and the latter was considered one of the Seven Sages of Greece. This prompted the Greeks to discuss how one might become a "good tyrant", if such a thing existed. One of the most interesting texts is Xenophon's Hiero, written in the 4th century BC - a fictional conversation between the historical poet Simonides and the historical tyrant Hiero of Syracuse. It goes through all the ways in which a tyrant's life is actually a nightmare of mistrust and groundless hatred, but suggests that there are ways for a tyrant to benefit his community and end up beloved by the people he ruled.