In this dissertation, I provide three studies of artistic practice in the era of the Great Depression. In each chapter, I write about a different set of artists working in the southeastern United States: I write about Walker Evans and the artistic and literary community located in the French Quarter of New Orleans, Louisiana (1926-1941); Edwin and Elise Harleston and their portrait studio in Charleston, South Carolina (1922-1931); and Bill Traylor and the artists who founded the New South Gallery and Art School in Montgomery, Alabama (1939-1940). Drawing from public and private archival collections, I consider how these artists made works that represented the South while they also made connections with artists and visual communities elsewhere; these connections placed them in dialogue with artists of the Harlem Renaissance, of American Regionalism, and of the Mexican Mural Movement. Although the artists in each chapter were from different Southern cities, they shared similar interests in the importance of developing and participating in artistic community. I situate each study in this dissertation in relation to a type of artistic practice. These types of artistic practice—documentary, portraiture, and exhibition—served as loci for Southern artists’ ideas about time and place. Southern studies have been haunted by the idea that the South always looks backward, to the past. In these three studies, I consider how Southern artists and their contemporaries in other places took different approaches to referencing the past and imagining a future for the South. The works made by these Southern artists—which are linked by their complicated relationships to race, history, and place—are largely absent from histories of American and 20th century art. Their absence tells us much about the stakes behind history writing. By bringing these studies into dialogue with other, existing, art historical contexts and communities, I trace how historical absence is constructed and why such absences are important to consider. The works in this dissertation are also linked by their difference from a kind of Modernism; in their multiple and discrepant modernisms, the artists in this dissertation made work which was both modern and not-modern, which looked backward while pushing forward. / text