Starring Jet Li (Li Lianjie), directed by Tsui Hark (Xu Ke), and set in the turn of the century Guangdong Province, China, the martial arts trilogy Once upon a Time in China raises a number of questions concerning history, China-West dichotomy, the dilemma of Chinese modernity, the structure of the “feminizing” gaze, and Westernized Chinese subjectivity. It has been suggested that Once upon a Time in China is a deliberate effort to retell and rediscover the past, and constitutes part of a response to the “Western gaze”—a (re)affirmation of Chinese masculinity and cultural superiority—and therefore augments the “materiality of Chinese identity.” This study, by revisiting this old series, tries to address these points with the intention of demonstrating contradictions in the discourse regarding Chinese cultural identity and modernization and thereby creating a consciousness of the disjunctures, discontinuities, and most importantly, the inherent hybridity in Chinese culture and identity. The recognition of a mutually feminizing gaze between the West and the East reveals orientalism to be a cultural logic that lies in the center of the “truly traumatic experience” of the post-colonial subject.