The relationship between the concept of authenticity and the project of nationalism is fraught with discrepancies. Is it possible to assess an Ì¢åÛåÏauthenticÌ¢åÛå narrative of nation with multiple interests at play in the project of nationalism? The clash of any of these interests can result in accusations of inauthenticity. Literary texts reflect how these anxieties of identity are negotiated, contested and/or accommodated and therefore can be tools for the examination of those anxieties. This dissertation examines the concept of authenticity as it relates to narratives about the Philippines and the juxtaposition of those narratives to Cuban, Puerto Rican, and American narratives. These four countries share an important connection, as all three manifest the literary reverberations of the War of 1898, which, connects Philippine literature, Latin American literature, Asian American literature and Latino/a literature. This dissertation aims to examine how texts test the boundaries of these nations and how texts test the boundaries among these disciplines. I first discuss national figures of the Philippines and Cuba, JosÌÄå© Rizal and JosÌÄå© MartÌÄå_, whose writings and personalities serve as templates for their respective nations. I then explore the complications of following this template in writers of the Filipino diaspora Jessica Hagedorn and Ninotchka Rosca, and the Philippine author Lualhati Bautista. I continue to examine strategies that authors such as Lualhati Bautista and Rosario FerrÌÄå© must employ to accommodate a history of colonialism and marginalized identity. How does choice of language affect the Ì¢åÛåÏauthenticityÌ¢åÛå of Bautista who writes in the official language of the Philippines, and how does that contrast with FerrÌÄå© who writes in the official language of Puerto Rico åÑ Spanish as well as the language of the metropole åÑ English? Finally I look at the complexities of an authentic, unhindered, national language through the gendered lens of translation theory.