The philosopher who triggered the discussion of media and play was Walter Benjamin. He distinguishes between traditional cloning techniques as the first technique and technical cloning as the second technique. He explains the characteristics of technology-based reproduction media as an extension of ‘play space’ (Spiel-Raum). The medium he paid attention to was film. Media theorist Marshall McLuhan describes media as “the extension of man.” According to him, play meets the conditions of a medium. Emphasizing the importance of play in the electric age, he quotes Schiller's philosophy of play. In particular, play in the electric age acts as a coolant to cool off the overheating caused by competition among media. Philosophical discussions about the media and play of our time, represented by the Internet and mobile phones, are taking place in various forms. In the digital age, play is deeply rooted in everyday life, and work and play are no longer opposed to each other. Norbert Boltz diagnoses the 21st century as the era of people who play. For him, play is the purest form of expressing the joy of life. Therefore, for him, play is a great stimulant for life. This article examines the claims of media and play by Benjamin, McLuhan, and Boltz, whose media theories representing the age of technological reproduction, electricity, and the Internet, and critically examines the limitations of the claims.