Often understood by some as an ideal(ized) neo-liberal space, the contemporary city presents those involved in creative milieux – its artists, cultural entrepreneurs, and others – with a new range of possibilities and attendant problems that are increasingly precarious. This talk addresses the way in which risk has been inflected in certain urban contexts, diminished and reconfigured by new strategies of play and humour that both embrace its potential and attempt to ameliorate its threat. The enchanted space of play is mapped onto urban sites where the ludic is embraced in the form of circumscribed, socially-sanctioned abandon but where its libidinal energy is sublimated and harnessed to something more utilitarian, and increasingly necessary, such as social networking. Far from being an end in itself, however, play now opens itself up to new forms of engagement, with others and with the city itself, a stylised solution to the dilemma of cultural life in the contemporary city. Geoff Stahl is a researcher and writer currently lecturing Media Studies at the University of Wellington, New Zealand. He has written extensively on urban subcultures and scenes, always with an emphasis on music making.