This paper focuses on the play, "Pictures of That Summer ('Ano natsu no e')," which is inspired by the "Paintings of the Atomic Bomb" project in Hiroshima. Through an analysis of its dramatization, the paper develops a theoretical framework for investigating the generation of the collective memory of catastrophes through works of art. In this light, through interviews, it then examines the experiences of professional actors involved in the dramatization. The actors struggle with the difficult task of constructing a communicative activity which conveys the memories of survivors, in a secondary manner, on stage. The paper discusses the means employed to address this challenge, and shows that intergenerational boundary crossing with respect to the transmission of the memory of catastrophes is supported by the crossing of boundaries between various educational fields, such as schools, museums, and theaters, and between various representations, in oral, pictorial, and theatrical form.