From the academic frontier of modernity and postmodernity, the author aims at exploring the fission between modernity and postmodernity and also the characteristics of postmodern cultural media from a philosophical vantage point. This paper illustrates three aspects of Western modernity: individual modernity, social modernity, and instrumental modernity, and it also clarifies the issues in modernity, starting by explaining three forms of the cultural fission: avant-garde, modernism, and postmodernism. The paper then demonstrates that the rise of postmodernity represents a new transformation and new characteristics of contemporary Western spirit, namely, the collision and compatibility of various concepts, in which popular culture and high culture, mass culture and elite culture, fashion and games as well as noise and silence have constituted an uncanny landscape of cultural media. This eerie landscape displays the indeterminacy of language, culture, art, consciousness, and aesthetics. From the perspective of theoretical innovation, the author proposes that the postmodern cultural media always displays its commodity and instrumentality, plays and entertainment, anti-culture and anti-art, replication and fabrication logically and practically as an outcome of post-industrial society. In conclusion, three critical issues are addressed: personal spiritual belief, the development of mass culture, and aesthetic principles. The postmodern cultural media has deeply influenced traditional culture, aesthetics, and how they are evaluated, resulting in cultural conflicts and a humanistic dilemma in the world of contemporary capitalism.