This article contributes to two relatively under-researched areas in the existing literature of Taiwanese popular culture and film studies – Taiwanese-language films (taiyupian) and port city cinema. We compare five case studies in Taiwanese-language port city cinema: Anping zhuixiang qu (Nostalgic Song of Anping) (Chen Yang 1969), Huilai anping gang (Back to Anping Harbor) (Wu Feijian 1972), Fenggui lai de ren (The Boys from Fengkuei) (Hou Hsiao-Hsien 1983), Haijiao qi hao (Cape No.7) (Wei Te-Sheng 2008) and角頭 Jiao tou (Gatau) (Li Yunjie 2015). Across each case, we analyse how the cinematic representation of port cities may have reflected social and cultural developments, changing (and unchanged) Taiwanese intersectional and cultural identities from the 1960s to the twenty-first century.