This paper presents an AI experiment of translation into emoji conducted on a glossary from Dante Alighieri’s Divine Comedy. The experiment is part of a project aiming to build up an automated emoji-based pivot language providing an interlingua as a tool for linguistic simplification, accessibility, and international communication: Emojilingo (emojilingo.org). The present test involves human (Emojitaliano) and machine (Chat-GPT) translations in a comparative analysis in order to devise an automated integrated model highlighting emojis’ expressive ability in transferring senses, clarifying semantic obscurities and ambiguities, and simplifying language. A first evaluation highlights Chat-GPT’s ability to deal with a classic archaic literary vocabulary, also raising issues on managing criteria for better grasping the meanings and forms and about the multicultural extent of content transfer.