This paper aims to reveal the differences of how the Oriental is reimaginated and the imagination’s reproduction and assimilation in Hollywood movies Joy Luck Club(1993) and Crazy Rich Asians(2018) which deal with the topic of the Chinese diaspora. The movie Joy Luck Club explores the black and white dichotomy of themes like the American and the Chinese, civilization and the primitive state, and wealth and poverty, and was analyzed as a work that shows the second generation immigrants’ desire to adapt to American society. The movie Crazy Rich Asians views the Chinese diaspora from a different perspective from Joy Luck Club. In the movie, the Asian’s personality is expressed as ‘rich’ and ‘crazy’, trespassing the binary framework and showing the new feature of Orientalism. This film confuses the Chinese-Singaporean with the mainland Chinese identity and also shows an aspect of Chinese diaspora that deviates from the struggle with self-identification and marks one’s full adaptation of American ideals. The difference between the two films’ reproduction of the Oriental signals different imaginations of Orientalism and the other fantasy of the assimilation of the Chinese diaspora into American society.