Near the beginning of a prolific and productive career as a writer and statesman, Claro M. Recto (1890-1960) authored two prize-winning dramas that were performed at the Manila Grand Opera House. Each of the plays—La ruta de Damasco (1913) and Solo entre las sombras (1917)—is a drama that represents the interactions of an ilustrado family in its relationship to the imposition of cultural practices and power structures under American rule. This essay proposes that in these dramas written by an ilustrado and performed for an interpellated ilustrado audience, the ilustrado home stands as a metonym of the nation, its family a synecdoche of the national community. As such, whereas the plays express the nationalist stance identified with members of the ilustrado class of educated elite, the dialogic enactment of tensions and conflicts among their ilustrado characters serves to work out the contradictions within the class and at the same time to legitimate the class’s hegemony and accommodationism in a Philippine society subjected to American colonial rule. The protagonists of La ruta are nationalist newspapermen who, facing persecution and censorship under the colonial government, are offered the choice between collaborating and resisting. The central character of Solo is a medical doctor who, in his struggles to conceal the fact of an adulterous relationship, reveals the effects of a “violent saxonization” that has undermined Philippine custom and identity. Both dramas thus complicate the post-1899 reimagining of the Philippine nation: as a community to be represented and led by what Osmeña called the “directing class,” which would declare nationalist objectives and defend the notion of a “Philippines for the Filipinos” while testing the limits of resistance to the American colonial institutions and registering the effects of their newly introduced values and practices on Philippine society during a time that saw the rise of the Partido Nacionalista of Osmeña, Quezon and Recto.