In this article, the authors discuss the potential for emancipatory pedagogies, which include practices like the use of digital tools and popular culture, to undo deficit constructions of Black and Latino males and their literacy practices. They discuss why such practices are not more readily available and visible in traditional urban school settings but how their use of digital tools and popular culture with urban Black and Latino males happens in "alternative" settings and outside official school contexts. The authors challenge the criminalization and policing of digital and popular literacies among Black and Latino males in urban school settings and reflect on the ways that they have witnessed emancipation and empowerment when these male students were not only allowed but "free" to engage in such practices.