Negotiating representations in increasingly complex multicultural contexts is central to educational work. The authors use Rosenbaum & Douglas's 2003 documentary Searching for the Wrong-Eyed Jesus to explore paradoxical representations of White Southern men. Notions of white privilege, while applicable, are insufficient when one considers the White Southerners' lack of access to political power and the cultural coding that presumes reactionary, violent racists inhabit the region. As they begin thinking through the film, the authors utilize its interpretive framework, a hip gaze, to reimagine insider/outsider representations and their connections to the broader question of power and education. While not politically powerful in itself, the cultural force known as hip is both hegemonic and counter-hegemonic and inverts traditional notions of power. Hip is a response to and a justification for institutional desires to make student behavior conform and to crush dissent. However, the authors argue that it is these actions that train students to compartmentalize social selves from private selves which eventually render citizens willing to exchange political and economic power for cultural freedom. They conclude that there is an opportunity for a discourse on class oppression that can compel students to integrate their social selves and private selves.