This chapter is dedicated to explore the relationship between entertainment, culture, and media art. Firstly, the positioning of entertainment will be described including the historical point of view and also focusing on recent digital entertainment technologies. It will be clarified that entertainment is closely related to the mental sustainability of human and therefore has a close relationship with culture and art. Then, based on this, further investigation will be carried out to explain how culture and technology could be combined together. Firstly, the relationship between culture and technology will be discussed proposing the concept of “cultural computing.” Then three typical research examples of cultural computing, “ALICE,” “ZENetic Computer,” and “Confucius Chat” will be described emphasizing how cultural issues could be treated using computer both in the Western culture and Eastern culture. As art is the core part of culture, as a next step the role of art, especially new art called media art where technology plays an important role, will be discussed. And, as an example, media art created by an Eastern media artist will be introduced as a good example of such media art treating cultural issues.