Every theory of metaphor faces the challenge of explaining the complex relationship between literal and metaphorical meaning. In this chapter, we analyze Hesse’s approach to metaphor, arguing that her original perspective sheds light on the contemporary debate on the literal-metaphorical distinction, going beyond how it is interpreted within the domains of semantics and pragmatics. To this end, we discuss the theoretical move that allowed Hesse to reject the primacy of literal meaning and the semantic-pragmatic distinction in her explanation of the interpretation of metaphorical meanings. Reference is made to ancient, medieval, and contemporary debates to underline the three theoretical steps upon which Hesse’s original view is based: (1) an approach to metaphor as an analogical process capable of reshaping previous uses of words and previous perceptions of reality; (2) a description of the analogical process as a classification that identifies similarities that constitute higher categories; and (3) the equation between word meaning and word classificatory uses, which explains how the discovery of new similarities and differences can modify the meaning of a word and create new relations between words.