The essay reconstructs Mariangela Ripoli’s intellectual path through two central strands of her research: American Legal Realism and the "Law and Literature" movement. Starting from her studies on Jerome Frank, Ripoli developed an inquiry into the language of law and the distinction between legal reality and fiction, identifying in Bentham and Olivecrona the forerunners of an anti-metaphysical critique of legal formalism. In the second part, the author highlights how Ripoli anticipated in Italy the debate on "Law as Literature", emphasizing the role of symbolic and narrative representations in legal education.