This chapter explores how Indigenous youth from two socioeconomically disadvantaged places - one in Australia's tropical north, the other just beyond the outermost edge of the Greater Sydney metropolitan area - marshal resources and find expressive voice through hip-hop music, dance and video production. In these locations, physical distance and poverty are conditions influencing the ability of creative artists to do their work, access opportunities and build careers. Yet remoteness is managed, and marginality negotiated through the expressive medium of hiphop and new recording and distribution technologies. Through their efforts, Indigenous hip-hoppers have built a new kind of network -semi-informal, political, transnational and often decidedly anti-colonial - that constitutes a new, vernacular, Indigenous creative industry in regional and remote Australia. But crucially, we also explore how physical distance and poverty are not the only barriers that creative artists negotiate. Young musicians navigate expectations of themselves and what constitutes 'proper' Indigenous performance in wider Australian cultural industries. Beyond physical and socio-economic marginality, cultural norms and expectations frame what are possible, producing and restricting creative opportunities. The chapter draws on collaboration from 2008 to 2009 between two researchers- one Indigenous, one non-Indigenous (both having grown up in the Southern Illawarra) -who brought to this project different goals and backgrounds. Andrew was at the time a PhD researcher on the Cultural Asset Mapping in Regional Australia (CAMRA) project. Rob is Indigenous and belongs to the Yirandali Aboriginal nation, in the Hughenden area of north-west Queensland. At the time of research he was a student and active member of the region's Indigenous hip-hop scene. This collaboration provided unique links and personal connections that fostered fieldwork.