In this article, the authors attempt to explore some of the ways in which youth subjectivities are constituted in the neoliberal order, the ways in which their behaviours are criminalized, and the harrowing manner in which schools, as one site, are complicit in a larger cultural disinvestment in youth. The authors accomplish this through an analysis of a drama activity with youth that aimed to "hold a mirror" up to the various policing measures inflicted upon a fictional group of workers (the youth in role) in order to see how this kind of theatre pedagogy and analogous thinking might explore people's sense of the imagination as "occupied space" in the current criminalizing of youth in schools. In the last section of this article, the authors attempt to come to grips with the more difficult pedagogical question of what it means to go beyond simply "unmasking" the issues and, how a democratizing pedagogy might usher in such a project. (Contains 7 notes.)