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This study uses literary texts from the twentieth century to explore the interaction between liberty and democracy at the heart of the American Dream. Of particular interest is the way in which the Dream is invoked and then called into question in Hemingway's To Have and Have Not (1937), Zora Neal Hurston's Their Eyes Were Watching God (1937), and Marjorie Kinnan Rawlings' Cross Creek (1942). These works demonstrate a failure of a social order meant to guarantee individual success. The protagonists are forced to counter expectations of normalcy concerning the identity politics of race, class, gender, and sexuality in order to achieve the Dream's goal of a good life rooted in domestic happiness.