This paper presents an AI experiment of translation in emoji conducted on a glossary from Dante Alighieri’s Comedy. The experiment is part of a project aiming to build up an automated emojibased pivot language providing an interlingua as a tool for linguistic simplification, accessibility, and international communication: Emojilingo. The present test involves human (Emojitaliano) and machine (Chat-GPT) translations in a comparative analysis to devise an automated integrated model highlighting emojis’ expressive ability in transferring senses, clarifying semantic obscurities and ambiguities, and simplifying language. A first preliminary 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.