This paper examines the high school media education textbook that Marshall McLuhan and coauthors published in 1977. "The City as Classroom" textbook provides an articulation of the practical implications of McLuhan's media theories. I offer an explication of this approach and its significance for contemporary media education, while articulating how McLuhan's perspective could bolster the educative potential of "critical media literacy," which can be distinguished from other forms of media education by its emphasis on examining the ideological content and power relations behind the construction of media messages. McLuhan's curriculum can be considered a form of critical media education, though it takes a broad approach that facilitates student inquiry within a multitude of mediated environments and includes examinations of media forms and grammar in addition to content. McLuhan's approach to media analysis offers possibilities for expanding the boundaries of critical media literacy by making an exploration of the tools that students use to mediate their experiences a key facet of media curriculum.