This chapter explores youth leisure and hip-hop as postcolonial practices via a case study of urban hip-hop with First Nations youth in Edmonton. It presents a case study of one hip-hop cypher to evaluate leisure as a central site in broader conversations and struggles for social justice, which is also a kind of cypher. The chapter discusses Cypher Wild YEG within the wider historical context of colonial injustices in Canada. Social justice has become something of an academic buzzword in recent years, and demands careful attention to relations of historical breadth and complexity. It analyses hip-hop performances in public spaces as showcases for social justice practices by Aboriginal-Canadian young people. Hip-hop is widely recognized as a cultural battleground, a culture that is 'burdened by its contradictions' of cultural resistance, containment and reproduction; it is a contested terrain where young people engage in radical acts of political performance.