Jacopo had not been many months in Florence before Bernardo Vettori sent him to stay with Leonardo da Vinci, and then with Mariotto Albertinelli, Piero di Cosimo, and finally, in 1512, with Andrea del Sarto, with whom he did not remain long, for after he had done the cartoons for the arch of the Servites, it does not seem that Andrea bore him any good will, whatever the cause may have been.
Pontormo painted in and around Florence, often supported by Medici patronage. A foray to Rome, largely to see Michelangelo's work, influenced his later style. Haunted faces and elongated bodies are characteristic of his work. An Example of Pontormo's early style is a fresco depicting the Visitation of the Virgin and St Elizabeth, with its dancelike, balanced figures, painted from 1514 to 1516.
Many of Pontormo's well known canvases, such as the early Joseph in Egypt series (c. 1515) and the later Martyrdom of St Maurice and the Theban Legion (c. 1531) depict crowds milling about in extreme contrapposto of greatly varied positions.
In the years between the SS Annunziata and San Michele Visitations, Pontormo took part in the fresco decoration of the salon of the Medici country villa at Poggio a Caiano (1519–20), 17 km NNW of Florence. There he painted frescoes in a pastoral genre style, very uncommon for Florentine painters; their subject was the obscure classical myth of Vertumnus and Pomona in a lunette.
Regardless as to the veracity of Vasari's account, it is certainly true that Pontormo's artistic idiosyncrasies produced a style that few were able (or willing) to imitate, with the exception of his closest pupil Bronzino. Bronzino's early work is so close to that of his Teacher, that the authorship of several paintings from the 1520s and '30s are still under dispute—for Example the four tondi containing the Evangelists in the Capponi Chapel, and the Portrait of a Lady in Red now in Frankfurt (at left).
In 1522, when the plague broke out in Florence, Pontormo left for the Certosa di Galluzzo, a cloistered Carthusian monastery where the monks followed vows of silence. He painted a series of frescoes, now quite damaged, on the passion and resurrection of Christ.
The large altarpiece canvas for the Brunelleschi-designed Capponi Chapel in the church of Santa Felicita, Florence, portraying The Deposition from the Cross, is considered by many Pontormo's surviving masterpiece (1528).
Perhaps as a result of Vasari's derision, or perhaps because of the vagaries of aesthetic taste, Pontormo's work was quite out of fashion for several centuries. The fact that so much of his work has been lost or severely damaged is testament to this neglect, though he has received renewed attention by contemporary art historians. Indeed, between 1989 and 2002, Pontormo's Portrait of a Halberdier (at right), held the title of the world's most expensive painting by an Old Master.
This early Visitation makes an interesting comparison with his painting of the same subject (at right), which was done about a decade later for the parish church of St. Michael in Carmignano, about 20 km west of Florence. Placing these two pictures together—one from his early style, and another from his mature period—throws Pontormo's artistic development into sharp relief. In the earlier work, Pontormo is much closer in style to his Teacher, Andrea del Sarto, and to the early sixteenth century renaissance artistic principles. For Example, the figures stand at just under half the height of the overall picture, and though a bit more crowded than true high renaissance balance would prefer, at least are placed in a classicizing architectural setting at a comfortable distance from the viewer. In the later work, the viewer is brought almost uncomfortably close to the Virgin and St. Elizabeth, who drift toward each other in clouds of drapery. Moreover, the clear architectural setting that is carefully constructed in earlier piece has been completely abandoned in favor of a peculiar nondescript urban setting.