The paper is devoted to the reconstruction of the main approaches to the interpretation of the rule-following problem in analytic legal philosophy. Skeptical arguments on the possibility of conducting the analogy between Wittgenstein’s arguments about following the rule and practice of application of legal rules and approaches of realism and antirealism about the nature of legal rules and their interpretation in practice are considered. The author justifies the statement that arguments of Wittgenstein cannot be directly used in legal language, however, his methodological approach to overcome the contradictions in legal terms using is useful and necessary.