The Hong Kong-born Canadian photographer and performance artist Tseng Kwong Chi mostly worked in the United States until the year he died in 1990. Upon arriving in New York in 1979, he started his career with a new name. By dropping his anglicized name Joseph and replacing it with his Chinese given name Kwong Chi, Tseng made a clear statement: this is my staged persona who refuses to assimilate to Western culture. This thesis deconstructs Tseng’s key works, including his party-crashing Met series, the decade-long East Meets West series, and the extended Expeditionary series. With his persona disguised by wearing a Mao suit and a pair of sunglasses, I argue that Tseng was a pioneer in the genre of Asian American performance photography and that his work foreshadowed the cultural jamming movement in his innovative use of détournement while it also critically comments on orientalism, cultural fetish, and Asian identity politics. Additionally, Tseng’s work served as a bridge, connecting art history with issues of Asian American identity. As a gay artist who worked mostly in the United States, his work was an early example of what Jachinson Chan has suggested as an alternative model of masculinity for Asian American men: that Asian American men can be free, independent, expressive, and willing to embrace femininity with their masculinity. As David Eng has argued, Tseng also bridged the fields of Asian American queer studies and diaspora studies. Moreover, Tseng carried the legacy of the first-generation Chinese American artists in the medium of photography and inspired the next generation of diasporic artists to explore Asian identity, and to contest the image of Mao and the power dynamics between East and West.