Using Critical Race Theory (CRT) and Tribal Critical Race Theory (TribCrit) as a theoretical framework, this dissertation analyzes a contemporary cinematic film directed by an American Indian filmmaker about American Indians and answers the question of whether the visual texts are unmasking, critiquing, confronting, and/or reinforcing reductive and stereotypical images of American Indians. Using Critical Thematic Analysis as a process, this dissertation interrogates Drunktown’s Finest (2014) to understand ways a contemporary American Indian filmmaker engages in counterstorying as a sovereignist action and simultaneously investigates ways the visual narrative and imagery in the film contributes to the reinforcement of hegemonic representations—the static, constrained, White-generated images and narratives that have been sustained in the hegemonic culture for over a century. With an increase in the number of American Indian filmmakers entering into the cultural elitist territory of Hollywood, moving from the margins to the center, I believe Natives are now in a better position to apprehend and reconstruct a multidimensional and complex American Indian identity. I posit that the reshaping of these mass-mediated images can only be countered through the collective and sustained fostering of a more complex imagery of the American Indian and that authorship of the representation is crucial to changing the hegemonic imagery of American Indians.