This article recounts how my own anthropological film, Cuba Sentimental (2010), was generated through a number of encounters and interactions among various actors. The film concerns a group of Cuban friends who left their country and traveled to various parts of the world. Its theoretical background is related to my formative years as an anthropologist in Japan, when the profound effect of "Writing Culture" shock was felt throughout the discipline. Rather than discussing what an ethnographic film is in terms of the subjects and methods of filming, I argue that films and images should be regarded as "anthropological" when they are made with the intention of creating an understanding of others and self-reflexivity, and they have that effect on those who view them. I arrived at that conceptualization of "anthropological" films participating in seminars by filmmakers, and listening carefully to what the interlocutors said. That understanding was subsequently elaborated by my reading a book by the documentary filmmaker Makoto Sato on documentary films (2001). Interestingly, what he insists on as crucial to good documentary making appears to have a lot in common with the so-called "quiet revolution" in contemporary anthropology. Generating my "anthropological" film became possible thanks to many different actors and events: the authors behind the "Writing Culture" shock, my Cuban friends'questioning of stereotypical representations of Cuba, and Cuban people's relationship with film in their daily lives. Further support came from grants-in-aid for scientific research, acceptance by the Global Center of Excellence (GCOE) Program of Osaka University, and encounters with people deeply interested in the kind of filmmaking that makes the audience listen to what the protagonists say. Cuba Sentimental was selected for and shown at various film festivals. Comments have varied depending on who the viewers are-anthropologists, filmmakers, or Cuban viewers. Opinions have differed even among people with similar backgrounds. Ultimately, I consider that what is important about this film is not that it was accepted and welcomed, but that it created interest in the people and the topic of the film, opening up an arena for discussion and comment. Cuba Sentimental has had many audiences composed of neither specialists about Cuba nor academics, but people with no prior interest in the people and topic of the film. Through the film, they have become aware of what happens in Cubans' lives. Furthermore, the film has also made some audience members interested in anthropology.