Ben Russell's headmap manifesto (1999) is an early and highly influential example of the discourse around commercial location-aware technologies that accompanied their emergence at the turn of the last century. Although numerous theorists acknowledge its influence on the fields of urban computing and locative media art, there have been few close analyses of the text and little consideration of its ongoing relevance in the current era of smartphones, location-based social networks and 'smart city urban planning initiatives. In this paper, I seek to address this shortcoming through a close examination of headmap and its influence on the discourse around what became known as 'locative media'. I argue that headmap offers a polemical, utopian vision of the world as it might have been, but also highlights the disparity between academic and artistic discourses around location-aware technologies and their current mainstream application.