This dissertation asks two questions: how did it feel to be left behind, defeated, and stuck in the U.S. South at the turn of the twentieth century, and how did people make new stories (or old ones) when they could no longer keep to the cultural scripts that promised success, freedom, and mobility? These questions illustrate how affects, feelings, and moods are more than psychological details but social testimony to the experience of living without the succor of a dependable historical narrative. To answer these questions this dissertation turns specifically to the period between 1890 and 1913 when the pressures of industrial capitalism, scientism, and white nationalism came to bear on the first generation of Americans living after the Civil War. In this, I turn specifically to literatures of the South.,My first chapter looks to the Confederacy, specifically the post-war life writing of Jefferson Davis, Emma LeConte, Jubal A. Early, Alexander Stephens, and James Longstreet. Using these canonical texts, I ask how white subjects negotiate political defeat before the emergence of nostalgic Lost Cause mythologies. My second chapter follows those who won the war. Here I examine how black self-help manuals like The College of Life (1895) and Progress and Achievements of the Colored People (1913) offered Washingtonian strategies for coping with a market-driven world outside of slavery and politics. These guides along with other popular sources frame a profound moment in black social history when the terms “optimism” and “discouragement” were frequently debated in black social discourse of the period. My third chapter looks to Paul Laurence Dunbar’s The Sport of the Gods (1902) and Charles Chesnutt’s The Colonel’s Dream (1905) in order to considers predations of racial capital actually looked like. Emerging from the shadows of this black self-improvement narrative—but before the Great Migration and the Harlem Renaissance—are two important novels: Charles Chesnutt’s The Colonel’s Dream (1905) and Paul Laurence Dunbar’s The Sport of the Gods (1902). These novels form a provisional genre, eschewing optimism in order to craft stories of surviving with what is left. Separately both illustrate the failed promise of mobility—be it physically migrating from south to north (or north to south) or moving into the bourgeoisie. My last chapter examines Ellen Glasgow’s Virginia (1913), a realist novel in which Virginia Pendleton, a prototypical antebellum Southern woman, finds her sentimental identity woefully unsuited for the New South. Glasgow’s novel knowingly moves between generic forms, modifying nineteenth-century sentimentalism with Spencerian evolutionary theory and the language of literary naturalism in order to redefine Lost Cause sentimental genres as themselves retrograde and unequipped for the inevitable triumph of modernity and the world it offered—one of reason, science, strong wills, and strong women. ,In looking to the edges I show how white and black men and women could often be bereft of a story of success but without an adequate story of their loss. In this way, this project is about living with pessimism. But it is more specific than that, too. The cultural fantasies of post-slavery freedom are not monolithic for those identifying as whites, for blacks, or Northerners and Southerners. Fantasies of overcoming difference and antagonism between whites and blacks, men and women also varied. Such fantasies and the practices that extend from them overlap and stretch –often to the point that their bearers admit their hollowness. This dissertation demonstrates how these kinds of fantasies hold and often fail to live up to their own promises. When people fall out of them, they must scavenge to build new, rickety, genres for continued survival. Transitional spaces, as this project shows, lead to transitional, unhandsome, and bewildered, feelings. In novels, memoir, self-help tracts, and newspapers, this project documents those people forced to adjust their dreams, their contexts of labor, and their emotions (sometimes poorly) when their expectations have been fashioned for another era and when the new world isn’t entirely new. Ultimately my project’s method demonstrates how to look behind dominant cultural genres in order to deepen our scholarly understanding of the defeat of political and cultural fantasies.