While pity had been seen traditionally as an untrustworthy rhetorical effect, beginning in the late seventeenth century, it is celebrated as a powerful and authenticating affect. My dissertation examines the historical rationale for the "rise" of pity in the eighteenth century and the ways in which its new sociopolitical status inspires formal innovation and alternative visions of ethical communion in contemporary literature. Anxious about change but eager to develop a vision of human nature and social coherence antithetical to the Hobbesean version, a growing number of writers made pity both the highest moral value and the central telos of aesthetic experience. Pity's defenders came to see in pity a providentially designed reflex built into the human body, a natural law of commonality, like gravity, that could draw otherwise hierarchically differentiated and self-interested individuals into a unified field of intimacy and social consensus. Pity, many felt, could transform suffering into a vehicle of spiritual reformation, social communion, and private moral orientation in a time of rapid change. As the century progressed, an increasing effort to define its parameters suggests that pity had become a dangerously flexible category. Recent critical efforts have typically treated eighteenth-century pity as having one of what I argue are a multitude of competing political and aesthetic functions: as a dubious vehicle of bourgeois ideology, for example, or as a support or mask for traditional hierarchies, or, alternately, as a positive Enlightenment ideal capable of effecting a new kind of relationship between equality and freedom. At the crossroads of progressive and conservative ideologies, pity provides literary history with an index of alternative visions of social order. My project begins by tracing a history of pity from Aristotle to Hobbes, including a discussion of the conditions that led to its unprecedented moral status in the eighteenth century. I then turn to argue, through a close analysis of works by Samuel Richardson, Henry Mackenzie, and William Wordsworth, that each author creates an aesthetic specific to his own aims, thereby reconstructing the category of pity for diverse political and literary ends.