This article explores the trajectory of the Italian comic archetype, ‘The Opportunist’, and how it illuminates, and allows us to draws connections between, numerous junctures of modern Italian history. The caricature ‘Arlecchino’, deriving from the masked ‘types’ of the commedia dell’arte of the fifteenth and sixteenth centuries, is an historic exemplar of the Italian ‘everyman’ who simultaneously evades and exploits the established order in order to ‘get by’, ‘get ahead’ and survive. Filmmakers of la commedia all’italiana such as Mario Monicelli, Dino Risi and Lina Wertmuller, employed this caricature of the wily – yet ultimately harmless – petty crook in their work. They did so not in order to reinforce prejudices of Italians as self-serving and apathetic, but in order to examine what it meant to ‘survive’ 20 years of Fascism and the socio-political turmoil of post-war Italy. Examining how this caricature has historically evolved according to its ever-shifting social milieu illuminates not only certain defining moments of Italian history, but also how this archetype has contributed to popular understandings about Italy’s past and its people.