Raven, Nanobozho, Wakdjunkaga, Ishtinke, and Coyote were a part of Native North American cultures long before anthropologists began to record their stories in the nineteenth century. Perplexed and captivated by these beings of diverse mythic origin, which they clustered together and identified as “tricksters,” anthropologists set out to impose meaning, variously drawing on ethnographic, structuralist, and psychoanalytic approaches. With the rise of identity politics in the last half of the twentieth century, indigenous artists, authors, and playwrights seized tricksters’ essence as a means of connecting to their cultural history without being locked into colonialist stereotypes about Native Americans. In this dissertation I examine the complexity and illusiveness of tricksters as a visual presence, approaching “trickster discourse” on a level that intertwines the disciplines of American art history, Native American studies, and cultural anthropology. Crossing previously unexplored territory between these disciplinary boundaries, I problematize current discourse that has adopted the term “trickster” as an identifier in Native American art theories, and, with consideration for North American tricksters in their historic and cultural contexts, I offer alternative interpretations that center on a more paradoxical reading of their contemporary functions in art.