This chapter is a scholarly play in four acts. It is inspired by a series of discussions between three legal researchers (Van Dijk, Epstein and De Vries) and a cultural theorist (Goriunova), about proposals to grant legal personhood to two types of non-human entities: nature and artificial intelligence. We queried whether doing so would help meet challenges such as environmental catastrophes and co-existence with opaque and unpredictable AI systems. In Act I (Divergences) Law and Critical Theory present their respective positions, but fail to gain any understanding of each other. Law defends a neutral legal pragmatism, while critical theory debunks all claims to neutrality. Act II and Act III present two fictional narratives: one plays out in a courtroom where a man is suspected of the murder of a river (Act II) and the other features an AI-system addressing the European Parliament (Act III). By discussing these counterfactual narratives in Act IV (Convergences), Law and Critical Theory are, at least partially, able to see how there could be cross-fertilization between their respective positions: one has to take into consideration how legal personhood operates both inside the court room as well as how it impacts the world outside; and one can travel towards an “enlarged pragmatism” that focuses on the possibilities of masks, fiction and play in expressing different voices, perspectives and ontologies.