Revision with unchanged content. Rebellion and Revolution are frequent political occurrences in today’s world, yet the links between such acts and what manifest from them are often misunderstood. Borrowing primarily from Eric Voegelin and Albert Camus, this work argues that the term rebellion applies to two similar but distinguishable experiences representative of the limits to human action and capacity. The political rebel is a man who rebels against an oppressive political regime. Opposing him is the metaphysical rebel whose action is inspired by a grievance against the nature of existence generally, as a human being, which he has interpreted to be oppressive. In this analysis these contradicting inspirations are matched to their juxtaposing consequences, and are exemplified through a literary analysis of Fyodor Dostoevsky’s novels, and a historical analysis of Václav Havel and the Velvet Revolution. This work may be of interest to the disciplines of political philosophy, history, and literature.