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Within contemporary mass media, many use film and literature to define cultures and identities beyond personal accounts. They are how we contextualize the past and frame the world around the time it is written, which is why it is important to have accurate representations of cultures and identities when they are depicted. According to many popular films — such as Sixteen Candles and Breakfast at Tiffany’s — to be an AAPI man means to be weak, creepy, and socially inept. While Jackie Chan and the spike of Kung Fu films in America tried to counter this emasculation, it resulted in an unprogressive and hypermasculine persona. Within recent depictions of AAPI characters and actors, the awkward and “beta” stereotype has transformed into sensitive yet strong men with complex characteristics beyond race. Projected stereotypes of AAPIs are often a reminder not only of the expected assimilation of many immigrants but also of the potential for social consequence when they are not fully incorporated into the so-called “melting pot.” Movies and books, while providing a vantage point for history and the world surrounding the time, are often inadequate renderings of identity and reality. By looking at three contemporary and essential AAPI texts — Jin Lee, portrayed by John Cho, in Kogonada’s 2017 film Columbus; Little Dog in Ocean Vuong’s 2019 novel on earth we’re briefly gorgeous; and Waymond Wang, portrayed by Ke Huy Quan, in the Daniels’ 2022 film, Everything Everywhere All at Once — we can track different masculinities that may not fit the muscular fabric of toxic American masculinity, but rather masculinities that fit the sensitive, reserved, yet strong AAPI men that are often under looked. If there is a discontinuous representation of reality, history will be misrepresented as well.