In this article, we will examine the role and place of the street musician, their contribution to the urban soundscape and the ways in which this has been informed and (re)shaped by recent advances in music technology. Despite their global omnipresence, street musicians have seldom been the focus of contemporary scholarly research on music-making and performance. Historically, the street musician has been perceived and depicted as a romantic folk figure, one moving through and working in the urban environment in an ad hoc manner. However, as our research reveals, through the diversification of street music and the steady uptake of new music performance technologies, street musicians are forging different forms of presence in contemporary urban settings, their music becoming an inextricable aspect of the contemporary urban soundscape. Drawing on face-to-face interviews and participant observation work conducted in Brisbane, Australia, during late 2010 and early 2011, we endeavour here to bring street musicians further into the academic dialogues surrounding musicians and performance and in doing so further highlight the centrality of digital music tools within the work of contemporary street music performance.