This thesis is a critical ethnographic exploration of Philadelphia graffiti as radical citizens’ media, and how the graffiti community is impacted by digital new media in regard to identity, social connection, and commodification. Previous research explores the traditions and practices that are specific to the Philadelphia graffiti community and how the medium affords transformative agency to practitioners, but existing research does not sufficiently explore how this subculture has been impacted by digitality and social media. Through both interviews with Philadelphia based graffiti writers and a critical virtual ethnography of local graffiti archives on Instagram, I explore the following research questions: How may graffiti be used as a form of transgressive, radical citizens’ media to challenge hegemony and elicit alternative imaginaries of resistance? How has the local Philadelphia graffiti scene integrated Instagram to their graffiti practices and community? I argue that graffiti contributes to both the urban physical landscape, but also the digital mediascape, specifically on the social media platform Instagram and as a medium has unique affordances that empower writers for social change. Further, I also argue that social media has influenced how graffiti is practiced, documented, and culturally received while also expanding opportunities for social change and community building. / Media Studies & Production