This article examines the concept of urban charisma as a quality that circulates through urban imaginaries and in the gestures and practices of everyday urban figures. Specifically exploring the figure of the gangster in Bombay cinema in the context of recent events of militant attacks in Mumbai, and tracing the empirical and cinematic transformation of the gangster into terrorist, this article argues that the cultural biographies of these figures, available through cinema, fiction, non-fiction writing and other forms of mass media are instructive as ‘reading principles’ through which chaotic and transitional urban spaces acquire legibility in popular imagination. As the city mutates rapidly, the mythic figure of the gangster and the enigmatic figure of the ordinary citizen-terrorist take on a new significance for understanding urban transformation precisely because these figures are framed by and in turn enframe these shifts most visibly, as these transformations become part of urban soul.