This essay is a study that combines the disciplines of film studies and cultural studies to analyze two contemporary German films “Erleuchtung Garantiert” (2000) and “Kirschblüten” (2008) by the filmmaker Dorris Dörrie. They both depict the pilgrimage of German tourists to Japan in the effort to restore a sense of authenticity to their lives. The study concentrates on the depiction of the encounter between Eastern and Western culture in connection with the theory of “Orientalism” by Edward Saïd. The analysis focuses on the confrontation of the illusory Japanese authenticity, as imagined by the German tourists, and the “real” Japanese authenticity as presented in the movie. This paper argues that although Dörrie criticizes her characters for their stereotypical understanding of Japanese authenticity, she also participates to some extent, in representing Japan’s “reality” in a stereotypical way. The stereotypes that are discussed in this study are those reminiscent of anthropological films about non-Western people and how these films contribute to the curiosity of Western viewers towards the “Other” and the Orient.