In the present work, a legal philosopher (Angela Condello) and a literaray scholar (Tiziano Toracca) develop the idea that a comparison between law and literature must be framed starting from the modes in which law and literature function. In this sense, they read law and literature as arts of compromising characterized by an analogous and yet, at the same time, profoundly different structure. Both, in fact, mediate conflicts between norms and transgressions, and more precisely between a principle of normativity (repression), on the one hand; and a principle of counternormativity (repressed), on the other hand. Through a progression in three steps, aimed at clarifying some peculiarities of law (1) and literature (2), by referring to examples of their interaction (3), the authors finally sketch some relevant hypotheses on why a placement across these two arts of compromising suggests some theoretical itineraries on their threshold.