William Reskimer became Page of the Chamber to Henry VIII in 1526. In 1543 he was made keeper of the ports of his native Duchy of Cornwall, and in 1546 he became one of the King’s Gentleman Ushers.

The background to the portrait includes the plant with the characteristics of both vines and figs that Holbein employed in portraits of his first visit to England. This portrait probably dates from early in Holbein’s second visit to England.

Simon George settled in Cornwall, but nothing is known of his court connections. He married Thomasina Lanyon and the carnation he holds might refer to their betrothal. He is shown in near-profile within the roundel format that evokes the coinage of classical antiquity, admired at the Tudor court.

His expensive clothing is painted with exquisite attention to texture and detail, notably in the depiction of light glancing off the stitched pattern of his silk sleeve. His cap is decorated fashionably with gold tags, violas and a badge which depicts the story of Leda and the Swan.

Robert Cheseman (1485–1547) was a trusted courtier, but it is uncertain whether he was one of Henry VIII’s falconers. He is shown stroking the soft breast feathers of an expensive hooded gyrfalcon. Holbein has dramatically illuminated the side of Cheseman’s face and the top of the bright pink satin of his sleeve, and skilfully evoked the texture and markings of the bird’s variegated feathers. There is a sense of expectancy in the contrast between the bird of prey’s momentary poise and Cheseman’s distant glance.

The large, almost-square format of the portrait is unusual for Holbein.

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John Godsalve (about 1510–56) took up the post of Clerk of the King’s Signet in 1531. He was elected MP for Norwich in 1537 and knighted in 1547. Holbein has emphasised Godsalve’s face and hair with dense and extensive use of ink, employing both pen and brush.

Despite the finished appearance of the portrait, it is probably a study for a painted portrait which does not survive. Godsalve’s glance back towards the viewer is particularly vivid; experimentation with the direction of the eyes is characteristic of Holbein’s portraits of the early 1530s.

Sir Thomas Elyot (about 1490–1546) pursued a career as a diplomat, MP and humanist writer. In 1531 his A Boke called the Governour, was published, giving humanist advice on the education of potential rulers of society. Margaret a Barow (about 1500–60) married Elyot in about 1522.

The way Holbein now supplemented his use of chalk with other media is particularly evident here. He used white heightening on the tip of Sir Thomas’s nose and on Lady Elyot’s forehead. Ink is used extensively, in the shading of the iris of Sir Thomas’s right eye and to add definition to the carefully modulated red chalk shaping Lady Elyot’s lips.

The French poet and courtier Nicolas Bourbon (about 1503–1549/50) was imprisoned at Paris following his criticism of those unfavourable to humanism and religious reform. On his release by Francis I in early 1535 he came to the English court where Anne Boleyn appears to have assisted him in finding work as a tutor.

Holbein has altered the drawing to include Bourbon’s hand, and his frontal gaze is at odds with the act of writing. The drawing may have been prepared for a lost painted portrait.

Mary Howard (1519–55?), the sister of the Earl of Surrey (shown adjacent) married Henry Fitzroy, Duke of Richmond, the illegitimate son of Henry VIII, in 1533.

Holbein shows her with downcast eyes wearing a plumed hat which he has sketched with swift bravura using ink and brush. Below are two outlines of her hat, with the jewelled initials ‘R’ and ‘MH’ for her name.

Holbein has made annotations to show that her dress is of expensively dyed red and black velvet, edged with gold as the yellow chalk indicates.

The drawing is incorrectly identified. Henry Howard, Earl of Surrey (1516/17–46), like Sir Thomas Wyatt (shown nearby), experimented with assimilating Italian and classical verse forms into English. He was extravagant in his quest for personal magnificence, and the subject of several portraits, including three by Holbein.

Though Surrey gazes straight ahead, Holbein subtly differentiates his right eye, on the shadowed side of the face, from the left. The chalk of this drawing is well preserved, particularly around the mouth. This is reinforced with a number of separate ink lines, adding to a sense of facial mobility.

Sir Thomas Wyatt (1503?–42) was imprisoned at the time of the disgrace and execution of Queen Anne Boleyn in 1536, but regained his position at court, acting as ambassador to the Emperor Charles V in 1537–9; this portrait may have been made before his imprisonment.

Wyatt was also a poet of great variety and invention; he introduced the Italian sonnet form to English, satirised court life in verse based on classical models and composed simple and direct lyric poems.

Lord Bergavenny (about 1469–1535) was a keen jouster and close friend of Henry VIII. Implicated in the treason of his father-in-law the Duke of Buckingham, he had regained the confidence of king and court by the early 1530s, when this drawing was made.

The freedom and vigour of the initial chalk drawing resembles those of Holbein’s first visit to England. Holbein’s ink reinforcements define the loosened flesh of the face and stress the bulk of Bergavenny’s nose. Holbein has defined Bergavenny’s neck and shoulders unencumbered by the two fur collars; their position remained unresolved.

Thomas Wriothesley (1505–50) was, like John Godsalve (shown nearby), Clerk to the Signet by 1530 and close to Thomas Cromwell. He became prominent at court and in 1540 was knighted and became joint Secretary to the King. From 1544–7 he was Lord Chancellor and was created Earl in 1547.

Like two others from the small group of those not originally preserved in the Royal Collection (one of which is shown nearby), the drawing has been cut from its background.

The inscription identifying the sitter as Anne Boleyn was made in the seventeenth century, but cannot be substantiated. The jewels on her headdress and on her bodice suggest she might have been a member of a noble family.

Holbein has paid great attention to her arched eyebrows and her large eyes with densely clumped eyelashes, using ink and brush to emphasise them.

The subject of this drawing wears a large bonnet over a closer fitting cap; the pin attaching it is clearly visible. Her costume resembles that worn by those of more modest social status, rather than courtiers of the nobility.

The direction of this sitter’s gaze and the way in which her head is turned further than her body suggests that her portrait might have been paired with that of a husband. The drawing has been cut out and stuck to another sheet of paper, evidently by a later collector.

The sitter in this drawing has not been identified. His shaped cap of blocked or stitched felt of the type worn by clerics such as Archbishop Warham and Bishop Fisher, and his hooded robe indicate that he too is likely to be a cleric.

The style of the drawing suggests a date in the mid 1530s. He might conceivably be Stephen Gardiner, Bishop of Winchester (about 1495/8– 1555).

It has been suggested that this man is a Hanseatic merchant, although his cap and clothing are similar to those worn by Sir Thomas Wriothesley (shown right), and if so this would be a notable exception to the disappearance of all Holbein’s preparatory studies for portraits of Hanseatic merchants.

Holbein has added a great variety of ink reinforcement to the chalk drawing, from the thickly shaded hair to the careful series of small lines emphasising the mouth.

The unidentified boy is wearing courtly dress and is stroking a pet marmoset. In its extensive use of colour including a blue background drawing closely resembles the drawing of Sir John Godsalve (shown to the left). It too was probably a study for a painted portrait as the characteristic use of ink reinforcing on eyes, nose and mouth suggests. The boy’s right hand overlaps what appears to be a parapet.

These drawings were possibly intended to be engraved on metal or stone, perhaps as embellishments to precious objects. The nobleman gazes on his armillary sphere, perhaps fruitlessly, like the astronomer Holbein mocked in his marginal illustration to Erasmus’s Praise of Folly of 1515.

In the other sketch a man offers a cup with a heart to a woman in a gable headdress. Lovers at the Tudor court gave each other small gifts including their portraits. Henry VIII’s inventory lists a ‘Harte of golde enameled with the kinges picture in it’.

The Italian inscription, meaning ‘And so desire carries me along’, is taken from Petrarch's ‘Canzoniere’, written about 1342; the unbridled horse was a symbol of passion. The rider is dressed in classical dress and boots, suggesting the picture was made for a patron interested in Renaissance poetry and imagery, as were some of those whom Holbein portrayed, for example Surrrey and Wyatt (also shown in this room).

The lozenge format was more frequently used to depict a coat of arms, but here the imagery seems personal, the type of image more often seen on small hat badges or other objects with emblems.