This paper analyzes urban space as one of the field of choice for contemporary advertising strategies and for their expression, in the light of the fact that following mass industrialization and the growth of the cultural industry it has become one of the places for the mirroring and full development of media operational logics. Therefore, the tracks found in urban spaces relate to the idea of spectacularization, which is declinated in multiple forms and employs various devices and languages, thus also showing the modification sustained over time by the semantization and fruition styles of the notion of space itself. In the light of all this, while the devices adopted by advertising communication within urban spaces are indeed related to the notion of spectacularization as they try to create stupor and involvement into citizens, outdoor’s traditional form is nonetheless more and more changing in a relational and performative sense, thus leading to a re-definition of the traditional field of outdoor as ambient advertising. What appears to be an evolutive phenomenon - marking, on the one hand, the rejuvenation of billboarding through the advancement of available technology, and on the other a growing consonance with the need for entertainment and interaction expressed with the purpose of creating a more involving relationship with the passerby/spectator – has become, in current global urban scapes, a prominence, of which a series of examples and cases will be here presented.