The following project examines the transformative power of literature against certain problems of the modern and postmodern experience as articulated by political theory. The primary concern is what theologian David Kyuman Kim calls "melancholic freedom," a condition wherein the intelligibility of the self has been compromised by the decreases in personal agency brought on by a modern disconnect from moral and ethical sources. As such, this work is situated within the contemporary debate on the interrelatedness of identity and agency, and thus the work of Charles Taylor will figure prominently. Much of the work of twentieth and twenty-first theorists has centered around attempts to resolve the complications that have developed in the wake of our modern era, to explain the tradeoffs and contradictions. Kim suggests the need for "projects of regenerating agency," which satisfy the following criteria: 1) provide suggestion of a religious imagination at work; 2) support a cultivation of the self; 3) demonstrate a search for moral identity and present opportunities for spiritual exercise; and 4) exhibit an aspiration toward a vocation of the self. It is my argument that engagement with the literary arts, either as a reader or writer, fulfills these conditions and presents an alternative site for regenerating agency. This expansion of Kim's work opens theory to wider application and joins political philosophy and literature in a common project of expanding the discourse on identity and agency. I will demonstrate how the writing and lives of Mark Twain and Walker Percy meet Kim's criteria for such a project. Twain and Percy as authors of projects of regenerating agency advance the case that art has the capacity to be instructive and illuminating as part of our moral discourses in ways that theory cannot replicate. Also, a reading of literature motivated by the concerns of political theory--in this case the discussion on identity, agency, and their points of intersection--allows us to reinvigorate the critical appreciation of these two authors.