A novel view on culture is developed by new technology. The dramatic change accelerates the globalizational interactivity, The phenomenon of globalization and the development of technological economy were mutually related. The new era is opened. Among the six times of Taipei Biennial in the 12 years, the issue of globalization was broadly discussed. The social differences and the cultural rupture, which were both caused by globalization, as well as the conflict between dramatic change and present reality were all transformed into an aesthetic category. The dialogue between cultures was expected.Based on Frankfurt School viewpoint, this essay covers from autonomous currents of Arts in capital society to the study of autonomous thinking of digital arts. Through Taipei Biennial, the history was queried. From the aesthetics study of technological culture of digital arts, the shifting to historical philosophy was provided. Through the curatorial argument of Taipei Biennial, as well as the social image depicted in the work of digital arts, a position to historical reading, functioning as a basis of cultural and social thinking, was proposed. From the social image depicted in the work of digital arts, the appearance of social reality can be penetrated. We can re-consider not only the history break due to the impact of technological process in Taiwan, standing in the platform of digital interaction, but also a cultural revolution caused by the history break. Though a language, which makes experience rebuilt by the cultural narration, the present society experience can be grabbed, the possibility of enlightenment and salvation can be evoked, the conversation with the history can be restarted, a bridge can be linked to the world, and the introspection of Taiwan Globalization can be constructed.