"A Crisis of Legitimacy" is a unique comparative examination of the question of legitimate rule, as observed through Shakespeare's "Richard II" and the contemporary presidencies of Bill Clinton and George W. Bush. Largely pedagogical, this article is the result of an active learning exercise, whereby students in a "Politics and Literature" course were asked to discover the criteria for legitimate political rule and then to apply said criteria to the reigns of Richard II, Bolingbroke, and the two most recent U.S. Presidents. The results revealed much about the complex nature of legitimacy, as well as the entangled nature of student self-interest in the political evaluative process. (Contains 4 notes.)