Two popular media forms are examined--the documentary film "Waiting for 'Superman'" and the HBO television series, "The Wire"--that present distinct, and at times conflicting, depictions of how to address educational inequity. Qualitative media content analysis was used to analyze the two media documents and to situate them within broader popular media representations of school failure. "Waiting for 'Superman'" depicted school choice and dismantling unions as one way to address school failure. The Wire, in contrast, suggested a more complex and uncomfortable portrayal of school failure where blame is not directed at teachers and schools exclusively, but instead encompasses a complex web of inequity due to bureaucracy, economics, culture, politics, and media coverage. The analysis suggests that media sources such as film and television can play a role informing the public on issues of school reform and should be critically examined as pieces of the larger puzzle of improving schools and addressing school inequity.