Vasari relates how the orphaned boy, "young, melancholy, and lonely", was shuttled around as a young apprentice: 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.

This early Visitation makes an interesting comparison with his painting of the same subject which was done about a decade later, now housed in the parish church of St. Michael Archangel in Carmignano, about 20 km west of Florence.

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 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.

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.

[2] The large altarpiece canvas for the Brunelleschi-designed Capponi Chapel in the church of Santa Felicita, Florence, portraying The Deposition from the Cross (1528), is considered by many Pontormo's surviving masterpiece.

The figures, with their sharply modelled forms and brilliant colours, are united in an enormously complex, swirling ovular composition, housed by a shallow, somewhat flattened space.

The startling contrast between the figures and ground makes their brilliant garments almost seem to glow in the light of the window between them, against the stripped-down background, as if the couple miraculously appeared in an extension of the chapel wall.

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 his Last Judgment, Pontormo went against pictorial and theological tradition by placing God the Father at the feet of Christ, instead of above him, an idea Vasari found deeply disturbing: But I have never been able to understand the significance of this scene, ...

Besides this, in one of the corners, where are the four Evangelists, nude, with books in their hands, it does not seem to me that in a single place did he give a thought to any order of composition, or measurement, or time, or variety in the heads, or diversity in the flesh-colours, or, in a word, to any rule, proportion or law of perspective, for the whole work is full of nude figures with an order, design, invention, composition, colouring, and painting contrived after his own fashion ...Vasari's Life of Pontormo depicts him as withdrawn and steeped in neurosis while at the centre of the artists and patrons of his lifetime.

Yet as the art historian Elizabeth Pilliod has pointed out, Vasari was in fierce competition with the Pontormo/Bronzino workshop at the time when he was writing his Lives of the Most Excellent Painters, Sculptors, and Architects.

Regardless of 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.