In this paper the problems of philosophy of play will be analyzed on the example of video games as a modern phenomenon of play. In the first part of the paper the terms of philosophy of play, play/game and video games will be defined according to general encyclopedias and lexicons, and they will also tried to be distinguished from the related ones. In the second part of the paper chosen problems of philosophy of play, like definition of game, characterisation of game, categorization of game, relationship between game and reality, game and art and game and sport, will be examined on the example of video games. Furthermore, soundness of Huizinga’s metaphor about magic circle which describes the limit between gameworld and real world will be observed and Jesper Juul’s definition of game will be critically considered, and then applied to video games. Scientific methods which will be used in the research are primarily comparative and historical method. The goal of this paper is to explore not only philosophy of play as a philosophical discipline, but also the phenomenon of video games.