This article explores the literature in the intersecting fields of media, technology and schooling in the United States across the past two centuries. It organizes the research from a social-historical perspective through a fictionalized interview with an archetypal third-generation urban public school teacher. This topography illustrates the problems and possibilities that emerge from the chronic push for technology in schools. Of particular mention are the privileging of orality and literacy through the common school reader, the mechanization of schooling through teaching machines and television, and the transformative yet still untapped potential of computers and the internet.