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The analysis of the two-sided portrait of Nano Morgante made by Bronzino in 1533 may allow discussion of the ineffable nature of spatial perspective from the point of view of art and geography. Painting and sculpture face diverse difficulties in mimicking and representing the real world. This issue has a challenging meaning for many scientific disciplines, including geography, when the representation deals with odd things and freaks of nature as diversely perceived by different cultures throughout history. Agnolo Bronzino and Filippo Brunelleschi were great artists and witty persons who practised a strong sense of irony in Florence, yet at different times. The paper illustrates the possibility of finding the same intellectual attitude to irony in their artistic behaviors and mastery. Using that kind of irony is also necessary to understand the very meaning of space and the relation between space perception and human senses.