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In comparing Alberti's De pictura and della Francesca's De prospectiva pingendi (in Tuscan), we are comparing the thought of a humanist with that of a craftsman, and the texts are so different that direct comparison is only possible after a detailed intellectual, social and practical contextualization. Although Alberti's text is written in Latin – for which he was readily dismissed -, both his and della Francesca's works proved to be of interest to a wide readership in their own times. They provide an early example of the intellectual crossover between low mathematics and high learning that was later so fruitful, and belong in the ancestry of the vernacular works of Galileo. But, written a generation apart, they otherwise seem to have little in common even though they are products of a shared culture and often overlap in their subject matter.