The relationship with an artificial intelligence has long existed in the history of human imagery. In Western cultures, it probably dates back to Ancient Greece, when the mythological figure of Talos may be considered as the first artificial creature invented with a purpose, and has been followed by an almost uninterrupted tradition of similar creations in human narratives, long before the name Robot was invented by Čapek in the XX century (The Royal Society, 2018). Artificial intelligences have been represented in all different kinds of narratives and recent research shows how these narratives have a profound influence on the real world, on the creation of an ecosystem of concepts and images and even in addressing the choices of scientific studies (Cave et al., 2020). Most significantly for our purpose, it also has an impact on addressing the pedagogical reflection and on contributing to the creation of teaching scenarios which translate imaginaries into teaching practices. The aim of this contribution is to focus on the manifold aspects that presents literary AI and on the intersections that may arise from these reflections, both in Italian and International teaching contexts.