This paper examines how The Gangster of Love (1996), the second novel by Filipino American artist and writer Jessica Hagedorn, dismantles ready-made assumptions about the construction of minority and mainstream cultures. Spanning the period from the 1970s to the early 1990s, Gangster depicts the life of Rocky Rivera, a Filipina American young artist. As it portrays Rocky's family and friends, the novel examines the drastic re-articulation of the US's self-image brought about by Filipino Americans and other groups marginalized as minorities by virtue of their ethnic, socio–cultural, and/or sexual identities. The narrative challenges dominant notions of who and what makes history, juxtaposing historical references with fictionalizations of real episodes and completely fictional incidents, and making a constant use of parody, irony, jokes and clichés. This paper studies Rocky's reworks of her multiple ethnic and sociocultural allegiances in connection with her passion for music and popular culture, placing these reworks in the context of the Philippines’ colonial and neo–colonial background and multi-cultural US history. It also considers succinctly how Gangster's postcolonial dimensions intersect with a feminist and postmodern consciousness in a gendered strategy of socio–cultural resistance and critique.