This paper explores the popular concept of the relationship between Taiwan and China as a feminine/ masculine dichotomy which has been constructed within Taiwan’s national imagination. First, I will focus on how this dichotomy has been created within the process of identity-shifting in Taiwan since the 1990s as manifested in Taiwanese pop songs. Second, I will demonstrate how it has been appropriated within the process of nation-building. Two primary questions will be addressed: How is the national imagination of Taiwan in Taiwanese pop songs constructed through maternal and feminine images? How is the matrilineal genealogy in Taiwanese pop songs appropriated by the opposition camp, namely the Democratic Progressive Party (DPP), to mobilize voters? I will investigate, from a cultural studies perspective, how cultural imagination has come to serve as the vehicle to formulate resistance, mobilize voters, gain power and, most importantly, reconstruct Taiwanese nationalism within Taiwan’s political limbo for decades. Furthermore, Margaret Somers’ discussion (1993, 1994, 1995a, 1995b, 1995c; Somers and Gibson 1994) of narrative identity is adopted as the framework for this paper in order to look at how identities are constructed within and across multiple realms. My research methods consist of conducting in-depth interviews and analysing texts.