This article explores Gabriele Basilico’s photographs of the contemporary Italian environment and argues for their status as both iconic – that is to say, distinctive, highly visible, and memorable – and anti-iconic symbols or images. The discussion first explores the anti-iconic impulse in Basilico’s work. It marks out his standing as one of the most prominent proponents of the trend in contemporary Italian photography which sought to counter the mythic view of the country’s landscape and highlights his involvement in the trend’s seminal exhibition, Viaggio in Italia (1984). The article then makes a case for the simultaneous iconic nature of Basilico’s photographs by looking at the 2007/08 exhibition Milano si mostra. 1 Km con Gabriele Basilico, examining the ways in which Basilico’s images were made into icons of Milan’s urban identity.