This workshop, which focuses specifically on advertising, elucidates pedagogies at the intersection of Black Feminist Theory, Hip-Hop Studies, and Film and Media Studies. By attending to constructions of gender, sexuality, race, class, citizenship, and other social, cultural and political markers in lessons involving popular media, I provide strategies that integrate popular media into the classroom through assignments and activities. I introduce techniques that help students understand the ideological and affective processes that work on and through us via media, in order to imagine forms of subjectivity that alter how we disruptively critique dominant representational practices now and in the future. Media has the potential to inspire, extend, and also limit the radical imaginaries that marginalized communities rely on to create new worlds. In this workshop we examine the practical dimensions of applying what M. Jacqui Alexander calls “pedagogies of crossing” in the act of teaching popular culture in the Dis/Information Age. That is, how do we account for issues of power, historical specificity, translocality, and the moments of crossing that are implied both within our consumption and creation of popular culture in the new age of “user-generated content,” as well as to the contradictory positions we bring into the classroom as both consumers and “cultural critics” (Alexander 2005)? Here, I invite participants to imagine popular culture pedagogies as a potential space of insurgent and fugitive knowledge production within and outside the university, but only as we engage in disruptive critique through our viewing experiences and analytical practices.