The quest motif forms the framework of the journeys undertaken by the three youthful protagonists of this study. In pursuit of selfhood, the non-conformist hero of the Post-World War II American South sets out on an uncertain path leading to confrontation and finally transformation. Joseph Campbell’s ground-breaking analysis of the quest motif is the starting point for the patterns described in these journeys. The quest takes the hero through a perilous post-modern landscape often in conflict with the legacy of the past. It is a place where the optimistic mainstream of the American Dream is juxtaposed with the trauma of human suffering. Through a close textual analysis, the author elucidates multi-faceted characters and thematic while shedding new light on a reading of Southern fiction. Although significantly different novels, important common threads are revealed linking the quest motifs in these works. This study examines William Styron’s Sophie’s Choice, Flannery O’Connor’s The Violent Bear It Away and Bobbie Ann Mason’s In Country.