The immigration reform of 1965 ushered in a tide of multiculturalism in the U.S. The new immigration changed the demographics of the U.S. as Asians and Latinos came to form the two largest groups of immigrants in the post-1965 era. The social debates on bilingualism between 1967, when bilingual education was first debated in Congress, and 1998, when Proposition 227 banned bilingual education from public schools in California, illustrate the negotiations around the incorporation of Asian Americans and Latinos into the national body. While the popular understanding of bilingualism in the 1960s viewed it as a disadvantage—a euphemism for linguistic handicap—the liberal approach to bilingualism tried to turn the liability of bilingualism into an asset. The two faces of bilingualism as liability and asset correspond to the oscillating position of Asian Americans and Latinos as racialized subjects and exemplary multicultural subjects in multiculturalism. In this dissertation, I place a number of well-known Asian American literary texts in dialogue with the debates on bilingualism to examine what the social discourse of bilingualism can offer for understanding of these texts and to see what the literary representations of bilinguals can show about the psychology and affective landscape of bilingualism that often go unnoted in the social discourse of bilingualism. I argue that the representation of bilinguals in Asian American and Latino literature shows the social negotiations around bilingualism that either result in the bilingual's becoming an exemplary citizen-subject or her perpetual relegation to a realm outside the social norms. The writers I examine, including Maxine Hong Kingston, Helena María Viramontes, Richard Rodriguez, Chang-rae Lee, Julia Alvarez, and Ha Jin, show the depth and breadth of a literary imagination that reaches into the heart of the psychological and social experiences of bilinguals. In their writings, the bilingual characters ruminate on the meaning of language and belonging, negotiate their state of racialization in and between two languages, and configure the place of language between identity and commodity. The literary bilingual's navigation of the various social values accorded bilingualism demonstrates the place of the Asian American and Latino subject within a managerial multiculturalism.