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In European and North American theater and film, the centuries-old practice of “yellowface”—white actors playing Asian-identified characters—has dominated the ways that Asians and Asian Americans have been presented. Since the 19th century, yellowface representations in American theater portrayed these characters as villainous despots, exotic curiosities, or comic fools. These roles in turn greatly reduced the opportunities for the employment and recognition of Asian and Asian American actors. Yellowface performance does not only misrepresent Asians and Asian Americans by limiting the kinds of visibility and opportunities that they might have, but it also supports the imagined distinctions between those values presumably embodied by white Americans and those associated with oriental others. Late-19th and early-20th-century plays such as George Ade’s The Sultan of Sulu (1902), Joseph Jarrow’s The Queen of Chinatown (1899), and David Belasco’s Madame Butterfly (1900) not only used yellowface acting but also expressed anxieties about interracial interactions and the potential for racial contamination produced by U.S. imperialism and Chinese immigration. Both yellowface and “whitewashing” (the erasure of Asian and Asian American characterizations from film and theater in order to benefit white actors) continue to be used in U.S. theater and film. In addition to protesting, Asian American performing artists have responded by creating alternative venues for Asian American performers and writers to make their talents known, such as Los Angeles’s East West Players (established in 1965). Asian Americans have also fully engaged with these issues through writing a host of plays that feature characterizations of actors who suffer the effects of discriminatory casting practices. Two plays in particular, David Henry Hwang’s Yellow Face (2007) and Lloyd Suh’s Charles Francis Chan’s Exotic Oriental Murder Mystery (2015) not only critique the legacies of yellowface representation but also prompt broader reflection on how contemporary Asian American identities are shaped by both political radicalism and “model minority” conformity. These plays re-appropriate yellowface to comment on the changing and contested nature of racial categories such as “Asian American” as well as the continuing problems of racial typecasting.