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This paper analyses the paradigms of interpretation and the evolution of the creative processes in music and law. Whether it is matter of a score or a law, the text is reborn through the work of the interpreter who, in dealing with the episte-mological problem of the understanding, has to harmonize the purity of the philo-logical reconstruction of the object with the need to actualize its sense. Moving from the creative character of every interpretation—neither the musician can be reduced to a mere executor of a concatenation of musical symbols on the staff as Stravin sky wanted nor the judge may be conceived as a bouche de la loi according to Mon-tesquieu’s theory—this work, after having discussed Gadamer and Betti’shermeneutical approaches to music and law, focuses on the issue of the limits to theinterpreters’ freedom. The interpretation here proposed revolves around improvi-sation, seen as a typical cultural practice of the aesthetic dimension of music.Improvisation, which from baroque to jazz does not correspond to the realm of absolute freedom, is used as a trait d’union in order to make a comparison with legalexperience. This is particularly true with the development of case law, whichbecomes increasingly problematic especially in the light of ‘‘liquid modernity’’,where the ‘‘polytheism of values’’ has been gaining strength. Seen from this per-spective, the comparison between the judge and the musician in their activity asinterpreters of a formalized system of signs highlights the controversial relationship between form and creativity, the accuracy of the text and the requisites deriving from the social context, certainty and justice.