This paper deals with representation of the trauma of World War II in three documentaries, namely Heat Sun (2007) from Taiwan, Habitual Sadness (1997) from South Korea and The Emperor's Naked Army Marches On (1987) from Japan, and specifically explores how the cultural production of documentaries becomes a healing conversation and a form of psychoanalysis. In these documentaries, three directors used different methods (just like oral history, companion or participant observation) to represent traumatic memories, experiences or narratives of subjects (whether Taiwanese-Japanese-soldiers, South Korean "Military Comfort Women" or Japanese soldiers) under imperialism. The whole cultural production (from shooting, editing to screening) of documentaries thus became some kind of healing conversation in the psychoanalysis therapy. This paper also argues that a dialogue contained in these documentaries is needed and opens the possibility of building connections among vulnerable or minority groups in East Asia to share historical experiences and trauma memories with one another, and to cooperate to rethink the influence or meaning of colonialism until now.