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Paintings of the 1500s

In 1505, Leonardo was commissioned to paint The Battle of Anghiari in the Salone dei Cinquecento (Hall of the Five Hundred) in the Palazzo Vecchio, Florence. Leonardo devised a dynamic composition depicting four men riding raging war horses engaged in a battle for possession of a standard, at the Battle of Anghiari in 1440. Michelangelo was assigned the opposite wall to depict the Battle of Cascina. Leonardo's painting deteriorated rapidly and is now known from a copy by Rubens.

Among the works created by Leonardo in the 16th century is the small portrait known as the Mona Lisa or La Gioconda, the laughing one. In the present era, it is arguably the most famous painting in the world. Its fame rests, in particular, on the elusive smile on the woman's face, its mysterious quality perhaps due to the subtly shadowed corners of the mouth and eyes such that the exact nature of the smile cannot be determined. The shadowy quality for which the work is renowned came to be called " sfumato ", or Leonardo's smoke. Vasari wrote that the smile was "so pleasing that it seems more divine than human, and it was considered a wondrous thing that it was as lively as the smile of the living original."

Other characteristics of the painting are the unadorned dress, in which the eyes and hands have no competition from other details; the dramatic landscape background, in which the world seems to be in a state of flux; the subdued colouring; and the extremely smooth nature of the painterly technique, employing oils laid on much like tempera, and blended on the surface so that the brushstrokes are indistinguishable. Vasari expressed that the painting's quality would make even "the most confident master... despair and lose heart." The perfect state of preservation and the fact that there is no sign of repair or overpainting is rare in a panel painting of this date.

In the painting Virgin and Child with Saint Anne, the composition again picks up the theme of figures in a landscape, which Wasserman describes as "breathtakingly beautiful" and harkens back to the Saint Jerome with the figure set at an oblique angle. What makes this painting unusual is that there are two obliquely set figures superimposed. Mary is seated on the knee of her mother, Saint Anne. She leans forward to restrain the Christ Child as he plays roughly with a lamb, the sign of his own impending sacrifice. This painting, which was copied many times, influenced Michelangelo, Raphael, and Andrea del Sarto, and through them Pontormo and Correggio. The trends in composition were adopted in particular by the Venetian painters Tintoretto and Veronese.