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Leonardo da Vinci is the painter of androgyny (bisexuality). This androgynous tendency Leonardo concealed behind strictly compulsive-neurotic features, apparent in his mode of living as well as in his face, but invariably, the youths he painted were feminine types. Likewise, in The Last Supper the principal figure and at least two of the apostles are feminine in type. In his portraits of women his androgynous tendency is not so pervasive, yet the 'half-figure of a nude woman' (Musée Condé, Chantilly) presents an interesting phenomenon—a young man with feminine breasts. Mona Lisa sat for this painting, the same Mona Lisa whose infinitely more famous portrait depicts that enigmatic smile which has confounded four centuries.
Freud, in his study of Leonardo, 1 traces this smile back to the master's memory of his mother's smile, a memory which came back to him with overwhelming intensity after his fiftieth year. Freud does not state explicitly that this smile is masculine. Nevertheless, utilizing the meagre biographical material which we possess on Leonardo, and his own experiences in psycho-analytic and mythological fields, he shows with extraordinary sagacity that Leonardo—as with all children in their earliest years—regarded his mother as a masculine creature, i.e. possessing a phallus.2 This conception which lay in the deeps of his unconscious never left him. Hence, we have reason to surmise that the smile which the world has dubbed "Leonardesque, " is also related to the mother-phallus complex. It has been characterized as frivolous, tempting, devilish, cynical, threatening, criminal; but all observers are unanimous in agreeing that none of these characterizations, nor divers of them put together, can drain this unique achievement in fine arts.