This article investigates the nature of student resistance to and engagement with digital media and twenty-first-century literacies in the English classroom at Last Chance High, an alternative high school. It traces the dynamic interplay of literacy practices and identity performances with and around digital media, exploring one student's engagement, disengagement, and resistance to officially sanctioned classroom activities. Drawing from a larger project, we highlight the ways in which the classroom teacher, Becky, a national board-certified English teacher and member of a digital media committee in the (US) National Writing Project, used digital media and twenty-first-century literacies in her classroom inquiry. While observing Terrin, a student at Last Chance High, over the course of a year, we identified key identity performances for her: "too cool for school," digital drama diva, and "driven mind." We explore her situated identity performances and digital practices as she fashioned overlapping and competing identities--from the resistant student intent on gaining social capital to the successful, savvy student who used digital tools to chart a different future.