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The analysis of Pino’s and Dolce’s dialogues is part of a larger research project that seeks to demonstrate how some Renaissance texts, using specific pedagogical and rhetorical strategies, played a decisive role in elevating art from the status of mere mechanical activity to that of a liberal art endowed with intellectual dignity. These two dialogues are commentaries on one of the central quarrels of the time: which art is the most dignified? Although Pino and Dolce adopt different strategies in their dialogues, respectively affirming the intellectual dignity of art without relying on literary sources and establishing who is the greatest artist, they both choose the genre of the dialogue to deliver their message in a more nuanced and multifaceted way. Including more than one fictitious interlocutor allows for a plurality of perspectives, especially useful when dealing with complex intellectual questions such as the one regarding the status of art.