This essay explores the colonial nature of the American road movie, specifically through the lens of how road movies treat the South according to Stuart Hall’s concepts of identity and Edward Said’s on Othering and the colonial gaze. To accomplish this, the essay analyzes the classic 1969 road movie, “Easy Rider”, and the more contemporary parody from 2008, “Harold and Kumar Escape from Guantanamo Bay.” The thrust of this paper becomes: if a progressive parody of road movies cannot escape the trappings of colonialism “Easy Rider” displays, perhaps the road movie itself is flawed.