In the early decades of the twentieth century, the imaginations of futuristic architecture and cities emerged. Several proposals and projects were closely linked with the artistic vanguards of the period, including cubist, expressionist, supremacist, and futurist explorations. European artistic renewal and progressive architectural utopias reveal the visions of a futuristic city, confronting the reality of new skylines in American cities. Fiction and architecture reveal interconnected effects, including the influence of futurism and the modernist movement from Italy, seen in architectural works like those of Luís Cristino da Silva in Portugal. The artistic expressions, aligned with futurist manifestos, were accompanied by creations that presented the possibilities of a new technological world, through authors such as Virgilio Marchi, Antonio Sant’Elia, and Mario Chiattone. We also include the innovations in modernist affirmation by Henri Sauvage, August Perret, among others. The influence of a significant legacy in numerous avant-garde works at the beginning of the century is recognized, especially in its relationship with early cinematic fiction, as seen in films like Metropolis, Just Imagine, and Things to Come. The interaction between Italian futurism, cinematic fiction, and modernist architectural production reveals a fascinating field of study, especially after nearly a century and highly relevant in the current context.