Sociocultural paradigm shift is closely related to the changes from the modern to the postmodern society. The modern paradigm of reason has changed to the paradigm of emotion while modern human view of homo sapiens has changed to stressing the importance of homo ludens. Moreover, the development of technologies and emergence of various media made better environment to enjoy culture contents in daily lives. These contents provided by various media became the new type of play culture as well as core of popular culture. Culture contents which are the play of this time as well as the key to popular culture must be open to the public at all times and must provide fun and enjoyment. In this article, the study will be focused on enjoyment and fun of culture contents in above aspect. First, the distinction of enjoyment and fun from linguistic aspect will be reviewed the term which number of researchers are still indiscriminately using. With the result, tend to reach the bottom of the generation principle of enjoyment and fun.