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Departing from the “Tiger Motheresque” tendency in Asian American literary criticism to dismiss adolescent play as an extravagance rather than a necessity, this article resituates Asian American child’s play as a racialized phenomenon. Readings of historical, ethnographic, and literary texts, including Jade Snow Wong’s Fifth Chinese Daughter, build on Sau-ling Wong’s influential argument of the “Asian American Homo Ludens” (1993) to reinterpret scenes of play in Asian American literature as sites of racial formation. The article tracks the ways that Asian American adolescents’ participation in family businesses and their oftentimes liminal position in recreational spaces produce a unique perspective on the artificiality of the work/play binary we frequently take for granted. The essay demonstrates how racialization has “worked” in twentieth- and twenty-first-century America not only through designated sites of labor but through the fraught and contested intersection between work and play.