This qualitative ethnographic study examines five American teenagers’ historical and current digitally-mediated multiliteracy practices within digital popular culture. The participants included three male and two female students of a private high school in the Midwestern United States. The study is framed by the notion that literacy is a socially, culturally, and historically situated discursive construct rather than a purely individualized cognitive endeavor. This social constructivist theory of literacy emphasizes the social conditions necessary to navigate the economic, social, and political worlds of the 21st century. The purpose of the study was to explore the students’ multiliteracy practices that they enact through their activities within digital popular culture. Data collection methods included synchronous interviews facilitated by video conferencing tools as well as observation of the participants’ online activities and member checks conducted via email and instant messaging. The analytic strategy employed during this study was informed by Clarke’s (2005) situational analysis method. The study’s findings indicate that literacy practices in which the study participants have engaged through informal learning activities within digital youth culture have had a much greater impact on enabling them to cultivate the multimodal literacies necessary within a postmodern digital era than have their formal educational experiences.