Good things tend to come in threes. That holds true I think in everything from Magi to Stooges. It certainly holds true when it comes to Leonardo Da Vinci's three greatest portraits. Three? Yes. Even the youngest school child is aware of the Mona Lisa. Painted in 1503 (though tradition has it that Leonardo worked on it for a number of years after that), it's without a doubt the most famous painting, let alone PORTRAIT, in the world today. Unfortunately it also suffers greatly from overexposure, having become something of a lightning rod if anyone wants to lampoon art, or to deflate art history whenever it becomes a little too pompous for its own good. Poor Mona has taken hits from everyone from Salvadore Dali and Marcell Duchamp to Mad Magazine. And while its an excellent piece of portraiture on a number of levels, of the three, I would count it as only his SECOND best effort.
An earlier work by Leonardo, dating from 1485, is so much more beautiful, natural, and interesting, in looking at it, it's hard to see what all the fuss is over Mona. The painting is entitled Cecillia Gallarani. In it, a lovely young girl holds a white ferret in her arms while gazing off wistfully into the distance. She is fashionably dressed with black pearls looped around her neck and hanging down behind an elegant, perhaps slightly elongated hand. Unlike the Mona Lisa, she seems warm and approachable. In this, the second of the three paintings (the Mona Lisa being the third), there is no evidence that Leonardo is playing with geometry or experimenting with any thing more mysterious than minimizing his subject's somewhat long nose to the point we are aware of it only after considerable study of her nonetheless attractive face.
The other Leonardo portrait is the first of the three, and to my way of thinking, the least attractive of the trio. It was painted in 1474 and is said to depict Ginevra de' Benci. Of the three, it's the only one I've seen. It's the only Leonardo in this country, probably the most valuable possession of the National Gallery of Art in Washington. In the Mona Lisa, Leonardo seems to have been experimenting with circles and ovals but he at least kept his geometric interests subtle. In this portrait, painted some thirty years earlier, when he was but 22 years of age, his interest in the circle almost literally leaps off the canvas, the roundness of her head and hair perhaps the first thing that strikes you in seeing the work. So help me, the effect is uncomfortably close to a "smiley face" except she's not smiling (perhaps not without good reason). Her skin is ivory and flawlessly cold, the face is colorless and bland, the curls in her hair, tight and labored. I find it stiff and unattractive. Of the three, I think it is easily the least successful portrait, although Vasari and a number of other experts would disagree with me on this. The best that can be said is that it was an early effort, and it would appear that he learned from it. Even of Leonardo, what more could we ask?