Underbelly (2008), Screentime’s $10.4 million, thirteen-part dramatization of the so-called ‘Gangland Wars’ from 1995 to 2004, tracing the rise and fall of career criminal Carl Williams, showcases a Melbourne largely unseen on the screen. That so much of Underbelly is shot on location means that its sets are the real spaces and places of Melbourne, overlaid with the scripted drama of what may have occurred there. This provides a new way of mapping the city, crime by crime, over time, a new way of understanding the Melbourne that the Kennett Government remade throughout the 1990s as an ‘entrepreneurial city’. It is our argument that it is this ‘entrepreneurial’ Melbourne that is being re-presented in Underbelly. Kennett’s entrepreneurial city is the context in which Williams operates and the philosophy to which he ascribes during his takeover of Melbourne’s drug trade. Drawing on examples from the 2008 Underbelly series, newspaper reports, Silvester and Rule’s 2008 repackaging of their underworld reports and a mixture of neo-liberal and entrepreneurial theory, this article explores Melbourne’s construction as an entrepreneurial city and how this has been represented, repackaged and experienced in a way Kennett himself could never have foreseen, through the Underbelly television series and the new markets this has opened.