The main topic of the paper is the analysis of Wittgenstein’s (later) understanding of rules, i. e. their nature in terms of a paradigm of “language games” in the context of Kant’s ideas on the rules of art. The submitted paper is a continuation and elaboration of my research and reflections on Kant’s concept of genius, and partially, on Wittgenstein’s thought, presupposing a mystical aspect of the artistic sphere. The first analysed connection corresponds with the theme of ineffability of rules as well as affinity of the ideas of both philosophers concerning the issue of the process of understanding rules, i.e. grasping them in practice. In the second, less extensive part I analyse the hypothesis for the dynamics of rules which is a natural consequence of a playful activity in the language use (Wittgenstein) or in creation (and reception) of works of art (Kant).