These paintings are famous for a variety of qualities which have been much imitated by students and discussed at great length by connoisseurs and critics. Among the qualities that make Leonardo's work unique are the innovative techniques that he used in laying on the paint, his detailed knowledge of anatomy, light, botany and geology, his interest in physiognomy and the way in which humans register emotion in expression and gesture, his innovative use of the human form in figurative composition, and his use of the subtle gradation of tone. All these qualities come together in his most famous painted works, the Mona Lisa, the Last Supper and the Virgin of the Rocks.
Early works
Leonardo's early works begin with the Baptism of Christ painted in conjunction with Verrocchio. Two other paintings appear to date from his time at the workshop, both of which are Annunciations. One is small, 59 centimetres (23 in) long and 14 centimetres (5.5 in) high. It is a "predella" to go at the base of a larger composition, in this case a painting by Lorenzo di Credi from which it has become separated. The other is a much larger work, 217 centimetres (85 in) long In both these Annunciations, Leonardo used a formal arrangement, such as in Fra Angelico's two well known pictures of the same subject, of the Virgin Mary sitting or kneeling to the right of the picture, approached from the left by an angel in profile with rich flowing garment, raised wings and bearing a lily. Although previously attributed to Ghirlandaio, the larger work is now generally attributed to Leonardo.In the smaller picture Mary averts her eyes and folds her hands in a gesture that symbolised submission to God's will. In the larger picture, however, Mary is not submissive. The girl, interrupted in her reading by this unexpected messenger, puts a finger in her bible to mark the place and raises her hand in a formal gesture of greeting or surprise. This calm young woman appears to accept her role as the Mother of God not with resignation but with confidence. In this painting the young Leonardo presents the humanist face of the Virgin Mary, recognising humanity's role in God's incarnation.
Paintings of the 1480s

Although the painting is barely begun, the composition can be seen and it is very unusual. Jerome, as a penitent, occupies the middle of the picture, set on a slight diagonal and viewed somewhat from above. His kneeling form takes on a trapezoid shape, with one arm stretched to the outer edge of the painting and his gaze looking in the opposite direction. J. Wasserman points out the link between this painting and Leonardo's anatomical studies. Across the foreground sprawls his symbol, a great lion whose body and tail make a double spiral across the base of the picture space. The other remarkable feature is the sketchy landscape of craggy rocks against which the figure is silhouetted.
The daring display of figure composition, the landscape elements and personal drama also appear in the great unfinished masterpiece, the Adoration of the Magi, a commission from the Monks of San Donato a Scopeto. It is a complex composition, of about 250 x 250 centimetres. Leonardo did numerous drawings and preparatory studies, including a detailed one in linear perspective of the ruined classical architecture which makes part of the backdrop to the scene. But in 1482 Leonardo went off to Milan at the behest of Lorenzo de' Medici in order to win favour with Ludovico il Moro, and the painting was abandoned.
The third important work of this period is the Virgin of the Rocks which was commissioned in Milan for the Confraternity of the Immaculate Conception. The painting, to be done with the assistance of the de Predis brothers, was to fill a large complex altarpiece, already constructed. Leonardo chose to paint an apocryphal moment of the infancy of Christ when the infant John the Baptist, in protection of an angel, met the Holy Family on the road to Egypt. In this scene, as painted by Leonardo, John recognizes and worships Jesus as the Christ. The painting demonstrates an eerie beauty as the graceful figures kneel in adoration around the infant Christ in a wild landscape of tumbling rock and whirling water. While the painting is quite large, about 200 × 120 centimetres, it is not nearly as complex as the painting ordered by the monks of St Donato, having only four figures rather than about fifty and a rocky landscape rather than architectural details. The painting was eventually finished; in fact, two versions of the painting were finished, one which remained at the chapel of the Confraternity and the other which Leonardo carried away to France. But the Brothers did not get their painting, or the de Predis their payment, until the next century.
Paintings of the 1490s
Leonardo's most famous painting of the 1490s is The Last Supper, painted for the refectory of the Convent of Santa Maria della Grazie in Milan. The painting represents the last meal shared by Jesus with his disciples before his capture and death. It shows specifically the moment when Jesus has just said "one of you will betray me". Leonardo tells the story of the consternation that this statement caused to the twelve followers of Jesus.The novelist Matteo Bandello observed Leonardo at work and wrote that some days he would paint from dawn till dusk without stopping to eat and then not paint for three or four days at a time. This was beyond the comprehension of the prior, who hounded him until Leonardo asked Ludovico to intervene. Vasari describes how Leonardo, troubled over his ability to adequately depict the faces of Christ and the traitor Judas, told the Duke that he might be obliged to use the prior as his model.
When finished, the painting was acclaimed as a masterpiece of design and characterisation, but it deteriorated rapidly, so that within a hundred years it was described by one viewer as "completely ruined". Leonardo, instead of using the reliable technique of fresco, had used tempera over a ground that was mainly gesso, resulting in a surface which was subject to mold and to flaking. Despite this, the painting has remained one of the most reproduced works of art, countless copies being made in every medium from carpets to cameos.
Paintings of the 1500s
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 brought about perhaps by the fact that the artist has subtly shadowed the corners of the mouth and eyes so 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, who is generally thought to have known the painting only by repute, said that "the smile was so pleasing that it seemed divine rather than human; and those who saw it were amazed to find that it was as alive as the original".Other characteristics found in this work 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, but laid on much like tempera and blended on the surface so that the brushstrokes are indistinguishable. Vasari expressed the opinion that the manner of painting 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 St. Anne the composition again picks up the theme of figures in a landscape which Wasserman describes as "breathtakingly beautiful" and harkens back to the St Jerome picture 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, St 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.
Drawings
Leonardo was not a prolific painter, but he was a most prolific draftsman, keeping journals full of small sketches and detailed drawings recording all manner of things that took his attention. As well as the journals there exist many studies for paintings, some of which can be identified as preparatory to particular works such as The Adoration of the Magi, The Virgin of the Rocks and The Last Supper. His earliest dated drawing is a Landscape of the Arno Valley, 1473, which shows the river, the mountains, Montelupo Castle and the farmlands beyond it in great detail.Among his famous drawings are the Vitruvian Man, a study of the proportions of the human body, the Head of an Angel, for The Virgin of the Rocks in the Louvre, a botanical study of Star of Bethlehem and a large drawing (160×100 cm) in black chalk on coloured paper of The Virgin and Child with St. Anne and St. John the Baptist in the National Gallery, London. This drawing employs the subtle sfumato technique of shading, in the manner of the Mona Lisa. It is thought that Leonardo never made a painting from it, the closest similarity being to The Virgin and Child with St. Anne in the Louvre.
Other drawings of interest include numerous studies generally referred to as "caricatures" because, although exaggerated, they appear to be based upon observation of live models. Vasari relates that if Leonardo saw a person with an interesting face he would follow them around all day observing them. There are numerous studies of beautiful young men, often associated with Salai, with the rare and much admired facial feature, the so-called "Grecian profile". These faces are often contrasted with that of a warrior. Salai is often depicted in fancy-dress costume. Leonardo is known to have designed sets for pageants with which these may be associated. Other, often meticulous, drawings show studies of drapery. A marked development in Leonardo's ability to draw drapery occurred in his early works. Another often-reproduced drawing is a macabre sketch that was done by Leonardo in Florence in 1479 showing the body of Bernardo Baroncelli, hanged in connection with the murder of Giuliano, brother of Lorenzo de'Medici, in the Pazzi Conspiracy. With dispassionate integrity Leonardo has registered in neat mirror writing the colours of the robes that Baroncelli was wearing when he died.
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