The American planter has mostly been presented as the epitome of the romantic cavalier legend that could be found in the fiction of John Pendleton Kennedy to Thomas Nelson Page: a man of chivalric manners and good breeding; a man of good social position; a man of wealth and leisure (Concise Oxford Dictionary). A closer scrutiny of the cavalier and genteel ethos of the time, however, reveals the inherent ideological inconsistencies with the idea of the gentleman itself, as the ideal came to be more and more perceived as an illusion and as challenges to traditional gender stereotypes came to redefine the nature and role of the Southern Gentleman. This study hopes to complicate the traditional delineation of hegemonic manhood with the aim to better understand how precisely the Old South’s masculine ideals were constructed and maintained over time, especially in times of crisis, and how southern elite males (re)defined, enacted, and/or maintained a distinctive Southern model of masculinity while others resisted, modified, or flouted those ideals. The work undertaken by this dissertation can thus be situated within the broad rubric of masculinity studies and its central axiom—the interrogation of the structures of power, domination, and hierarchy. Enriching masculinity studies of the Old South, this critical study of Southern American fiction attempts to respond to the invitation of historians like Stephen Berry or Craig Thompson Friend in striking a commendable balance between conceptualizing larger historical questions and narrating the intimacies and complexities of Southern men’s individual lives. Taken collectively, these novels continue to explore this fertile field by moving outside the “confines and confidences of elites” (Peel 1). Because it complicates any simple equation between honor, mastery, and manliness, and because it seeks to revisit traditional conceptualisations of gender, I hope that this study will open new ways of thinking about the privileges and wounds of a masculinity that has been considered by most as the normative, invisible, and unquestioned referent from which to measure marginalized others—foreigners, women, or non-whites.