This thesis explores the pervading feeling of the Gothic in the life and songwriting of Tennessee blues musician Ray Cashman. I argue that Cashman emotionally responds to the South through the framework of the Gothic to assert his identity as a white southern working-class male. As a reader, writer and performer, he trespasses the lines of race and class. The ethnographic fieldwork I conducted in Tennessee, Georgia and North Carolina between 2015 and 2017 led me to reflect on the intriguing relationship between blues, southern Gothic literature and white working-class culture in the South. The songs written by Cashman often express a feeling of desolation, bleakness and decay, invoke a sense of nostalgia for a bygone time, or describe eerie landscapes and supernatural presences. Cashman also retells southern Gothic stories, like “Snake Feast,” inspired by Harry Crews’s A Feast of Snakes.