Many people have experienced a peculiar feeling of freedom, of the world being open before them. This is the feeling evoked by phrases like “free as a bird,” “the freedom of the open road,” and “free spirits.” Drawing on a study of literary characters, I develop a phenomenological profile of spontaneous freedom, arguing that we experience spontaneous freedom when we feel that our actions are not fully settled in advance by our own consciously endorsed practical identities, plans, or prior decisions or those of other agents. I argue that the experience of spontaneous freedom is valuable because it is a necessary precondition for the creation of a certain sort of beautiful, creative art—the art that Kant calls works of “genius”—and because it helps us to confront existential anxiety by seeing that we extend beyond our rational, deliberative natures. Appreciating the value of spontaneous freedom requires rejecting or amending some prominent strands of contemporary ethical theory: “integrity theories,” such as Christine Korsgaard’s theory of self-constitution, contend that in order to be a good agent, or in order to be an agent at all, one must constitute oneself through rational deliberation and planning. Such views rule out experiences of spontaneous freedom for well-constituted agents because experiencing spontaneous freedom requires acting in a manner not antecedently fixed by one’s own plans, decisions, or consciously endorsed practical identities. I further argue that respecting the value of spontaneous freedom requires organizing political and social institutions to ensure that there are not large swaths of people’s lives in which they are completely cut off from experiencing spontaneous freedom. Respecting its values also requires that political and social institutions avoid trying to control or manage how people behave in those domains, like artistic creativity, where the value of spontaneity is at its peak. Finally, I suggest that certain sorts of social practices and institutions can predictably occasion experiences of spontaneous freedom, even though such experiences cannot be brought about at will. By encouraging play, games often provide at least a limited experience of spontaneous freedom.