Represented as a male-dominated space, the office is a privileged site of production of masculine identities in comedy Italian style. The high-ranking male clerical worker is therein depicted as a paradigm of successful masculinity in the Italian economy’s boom years. A trademark of successful masculinity, office design and its filmic representations has evolved throughout the decades, to reflect status and rank, and also a muted aesthetic taste. Comedy Italian style was not the first to represent office interior space as much as to appropriate it (alongside the restaurant, the beach, and the modern kitchen) to express a new paradigm of success and participate in the establishment of modern societal practices. Failure to live up to these standards of professional and, most importantly, financial success is at the center of most comedies Italian style depicting life in the office. This essay considers films such as Gianni Puccini’s 1959 L’impiegato, Dino Risi’s I complessi (1965) and Vedo Nudo (1969), along with some selected examples from 1970s Fantozzifilm series. In the cyclical reiteration of his failure, Fantozzi is the antithesis of the ideal of the man of success, by definition the climatic point of a gradual process of self-betterment, which the films’ very episodic nature precludes.