The drawing is a preparatory study for the portrait dated 1535 shown nearby, which appears to have been produced in Holbein’s workshop. There are hard chalk and metalpoint reinforcing lines over almost all the contours of the drawing, covering the head, ear and hat as well as the lower part of the body, but omitting the left-hand side of the face. These must result from the transfer of the drawing.

The dates inscribed on the corresponding painted portrait have plausibly suggested the sitter might be Sir Ralph Sadler (1507–87), appointed Clerk of the Hanaper in 1535.

This portrait is based on the drawing by Holbein shown nearby. The contours of the portrait match the drawing precisely, following its incised lines. The painting itself, while very close to Holbein’s manner, is weaker in execution than portraits which are certainly Holbein’s; the hands, which Holbein usually added to his compositions at a later stage, are disproportionately small and narrow.

The portrait was most probably produced under Holbein’s supervision by an unidentified assistant who must have been working with him in England.

This drawing is extremely similar in technique to others by Holbein, including the manner in which ink and brush are used to define the eyelid and lashes of the right eye. However, the abrupt manner in which the head is attached to the very broad shoulders is uncharacteristic of other drawings, and the chalk drawing of the body appears confused. These characteristics suggest an assistant may have completed what Holbein had begun, which was perhaps not much more than the face.

The frontal format and deep blue green background resemble Holbein’s portraits of the 1530s, especially those of Hanseatic merchants. The format of the small roundel is similar to other works by Holbein produced in this period. However, the somewhat flatly descriptive manner in which it is painted differentiates it from portraits executed by Holbein himself. The artist was conceivably a workshop assistant from the Low Countries.

John Bettes is recorded as a court painter to Henry VIII from 1531, and was also paid for portrait miniatures.

This portrait has been substantially cut down and would originally have showed the sitter at three-quarter length. Like several portraits by Holbein it is painted over a pink priming. The background was originally blue, but the pigment used has discoloured.

The painting technique however is not very close to Holbein: the fur is much more loosely painted, the curling hair of the beard flatly decorative. Possibly Bettes imitated Holbein’s use of pink priming, but is unlikely to have assisted him.

This painting was commissioned to commemorate the unification of the Company of Barbers and Guild of Surgeons in 1540.

To the left of Henry VIII are the royal physicians Dr Butts and Dr Chambers; Holbein’s individual portrait of the latter is displayed in Room 9.

Karel van Mander’s life of Holbein, published in 1604, states the painting was finished by another artist after Holbein’s death in 1543. It is likely that the painting was largely executed by Holbein’s workshop assistants.

Further heads on the right were added in the 1550s, but the head of Henry VIII is clearly based on Holbein’s image.

This large, bold chalk drawing closely resembles Holbein’s lost frontal image of Henry VIII in the Whitehall mural (Room 4). The frilled collar, seen in the version from Liverpool displayed nearby, differs from that seen in Holbein’s cartoon and presumably reflects what Holbein ultimately painted.

The close, right-handed shading is unlike drawings by Holbein, suggesting this is not a copy of a lost drawing, but is most likely to be a contemporary copy of Holbein’s painted image.

Hanns Swarttung, whose name is inscribed on the back of the drawing, might be the name of an assistant of Holbein.

This full-length portrait is one of the earliest of those closely based on Holbein’s image from the 1537 Whitehall wall painting (Room 4). Its history suggests it was made for the family of Queen Jane Seymour, possibly for her brother Edward, the Protector Somerset.

Copies of Holbein’s final original working drawings may have been made available to the painters of such works; an associate of Holbein’s workshop would have had ready access to them. Some aspects of the style of painting resemble Holbein’s, though there are significant differences in the manner of underdrawing below the surface.

John Fisher (about 1469–1535) became Bishop of Rochester and Chancellor of Cambridge University in 1504. As a result of his opposition to Henry VIII’s divorce he was imprisoned along with Sir Thomas More and beheaded. The pink priming of the paper suggests that the drawing must date from the early 1530s, when Fisher was already an opponent of the King’s policies and in poor health. No painted portrait based on the drawing survives.

The Italianate inscription seems to refer to Fisher’s execution.

This portrait is one of a small group of sixteenthcentury workshop patterns; all the others represent subjects from the reign of Elizabeth I, suggesting this pattern is of the same date.

The outlines of the pattern correspond closely with those of the Holbein drawing shown nearby. The pattern was not made directly from Holbein’s drawing, but was transferred from another pattern: close examination of the outlines has revealed the small charcoal dots characteristic of pouncing, a process by which charcoal was forced through small holes pricked along the outlines of the drawing to be transferred.

Sir Nicholas Carew (about 1496–1539) was Henry VIII’s Master of the Horse from 1522, and a favourite courtier until his implication in treasonable plotting by the Marquess of Exeter led to his execution in March 1539.

In its vigorous and subtle use of black and coloured chalks alone the drawing belongs to the period of Holbein’s first visit to England in 1526–8. Holbein has defined the headgear in monochrome (the colour note indicates the turban was to be of cloth of gold), but creates in coloured chalk a detailed record of the varying tones and colours of the beard.

The head of the portrait of Sir Nicholas Carew is based on the drawing by Holbein shown nearby. Unusually, this is slightly larger than the drawing.

The portrait shows many close connections with Holbein’s techniques, for example in the different types of gilding used and the approach to flesh painting. Such similarities of manner, as well as technique, suggest that the painting was carried out by a contemporary with a close knowledge and understanding of Holbein’s work. It may conceivably be connected with a tapestry portrait confiscated after Carew’s execution in 1539 and recorded in the inventory of Henry VIII.