The iconography and iconology of Roman theatres of the Imperial age are here regarded as a keystone to understand the role and the cultural and political meaning of theatrical buildings in a society based on philanthropy. Starting from this critical assumption, the essay inquires, within a contextual view, into both the theatrical building policy pursued by Augustus in Rome and the spreading, in a few decades starting from the Augustan era, of great stone theatres in Roman provinces. An extraordinary flourishing, that led to a number of urbanistic, iconographical and iconological effects. A special attention is dedicated to the theatres of Augusta Emerita (Mérida) in Spain (consecrated in 16-15 b.C.) and of Leptis Magna in Libya (inaugurated in 1-2 a.D.): spaces devoted to the imperial cult and loyalty; and also to the inauguration in 80 a.D. of the Flavian Amphitheatre, alias the Colosseum.