Rightfully deemed one the most cinematic of all Italian writers, Italo Calvino has been an endless source of inspiration for contemporary directors and visual artists. Calvino, however, had an ambiguous relationship with the world of cinema. Despite being an avid moviegoer for most of his life, he displayed both a fascination with and a certain disdain for film. While cinematic adaptations of his literary works have been rare, and not always successful, on the 100th anniversary of his birth, many artists are seeking to bring his life and work to the screen. This essay revisits Calvino’s “difficult love” for cinema and engages in a critical conversation with director Duccio Chiarini about the making of a documentary film on Calvino conceived for a wide, public distribution. The interview discusses the challenges of creating a portrait of a polyhedric writer while balancing creative impulses, material conditions, production demands, and other contingencies that shape a film project. The last section examines Chiarini’s film, Italo Calvino: lo scrittore sugli alberi (2023), which interweaves extracts from Il barone rampante with interviews, letters, photos, and drawings, and previously unseen home movies, offering viewers an intimate encounter with the writer.