The following essays were inspired by talks delivered at the 2015 Association for Asian American Studies annual conference, where we commemorated the fifty years since the 1965 founding of East West Players (EWP) in Los Angeles. Currently led by artistic director Tim Dang, EWP is known as the first and longest-running Asian American theatre company. It has played a crucial part in the training of Asian American actors and the formation of other Asian American theatres across the nation and in the development of new plays and productions that articulate and challenge how Asian America is understood and represented. Through reflecting upon the past, present, and future of EWP, our essays contemplate the most significant questions about Asian American theatre practice: how theatre engages the multiple and even contradictory aspects of what is Asian American, the panethnic racial category that is consistently challenged by the diverse cultural practices, communities, and identities it purports to describe. EWP's history illustrates the multiple dimensions of how Asian American theatre can challenge the limited prescriptions, labels, and packaging so often used in talking about race both inside and outside the theatre.