This article examines a dramatic aporia in modern European intellectual history, involving what it calls “perspectival thinking”—a way of thinking in which an individual assumes and thinks from the perspectives of others. This paradox appears in the work on totalitarianism of Europe's three foremost thinkers on totalitarianism—Hannah Arendt, Arthur Koestler, and George Orwell. Examining their explorations of perspectival thinking, this article argues that, taken together, they are strikingly discordant. While Arendt exalts it, Koestler and Orwell problematize perspectival thinking, and Orwell even sees it as evil. The three thinkers thus articulate a dramatically polyvocal understanding of perspectival thinking, creating a remarkable dissonance in modern European thought.