Jakob Fugger ‘the rich’ (1459–1525) was the most famous member of the Augsburg merchant family, bankers to the Habsburg family. No painted portrait survives to correspond to this subtle and delicate drawing and it is uncertain if one was intended.

The ink reinforcements resemble the manner in which Hans Holbein the Younger added ink to many of his own later drawings, but the effect here is harsh rather than clarifying. They appear to be the work of another artist, rather than Holbein the Elder himself.

Sigmund Holbein (active 1501–1540), the brother of Hans Holbein the Elder and uncle of Hans the Younger, was a member of the family workshop in Augsburg. He collaborated with Hans the Elder in painting large altarpieces.

The format of this small drawing is similar to many other surviving vivid portrait drawings by the elder Hans Holbein. They were often used as the basis for figures in altarpieces rather than for individual portrait paintings.

On his death, Sigmund left Hans Holbein the Younger his painting tools.

These strongly characterised male heads served as models to be copied for re-use in the Holbein workshop in Augbsurg. The head in the top left is an exaggerated version of one used in reverse by Hans Holbein the Elder in his altarpiece known as the ‘Grey Passion’, itself adapted from the work of the Netherlandish artist Dirk Bouts. On the reverse is an inscription with the names of Hans and Ambrosius, Holbein the Elder’s sons. This may have related to an adjacent drawing in a workshop pattern book, rather than this one.

One hand grasps a coin, another holds a staff. Similar sheets of studies of hands which Holbein the Elder made at different periods can be related to his preparations for specific painting commissions, but the purpose of these sketches is unknown. The careful description of the varying angles of the hands, evidently studied from life, can be compared to Hans Holbein the Younger’s studies of the hands of Erasmus, also using metalpoint, displayed nearby.

This is Hans Holbein the Elder’s design for the reliquary of St Sebastian shown nearby. There are some differences to the finished work, notably in the relationship between the saint’s arms and the forking of the tree branches to which they are attached. The saint is drawn standing on a small mound whereas in the reliquary he stands on a flat surface.

The drawing does not include the figures of the Virgin and saints on the base, which were presumably the subject of a separate study.

The Basel goldsmith Balthasar Angelroth (about 1480–1544) commissioned Holbein to paint the façades of his house on the corner of the Eisengasse, associated since 1401 with dancing. This drawing shows one side of the façade, with a frieze of dancing peasants above an arcade. To the left is Bacchus and above is the figure of a soldier who may be intended to be Mars.

The spectacular design contributed greatly to Holbein’s reputation in Basel, showing brilliant manipulation of illusionistic space and the most daring uses of perspective.

Holbein shows the humanist Erasmus (about 1467–1536) writing in an interior, in the traditional profile pose often used for depicting saints. The text, no longer legible here, but shown in a second version of the portrait at Basel, is Erasmus’s Commentary on the Gospel of St Mark, dedicated to Francis I of France, and completed in 1523. This suggests that the portrait was made in the same year in which Holbein also painted Erasmus in three-quarter face view, shown nearby. This portrait too may have been sent to England. Its simpler, more intimate character suggests it was sent to a friend rather than a patron

This is almost certainly the portrait which Erasmus sent in 1524 to his patron Archbishop William Warham (shown left). Erasmus must have composed the classical inscriptions: on his book is a reference to his ‘Herculean labours’, while on the shelf is a punning tribute to Holbein’s skill: ‘it is easier to criticise me than to imitate me’.

Around a powerful depiction of the ageing humanist’s face, Holbein constructed a halflength composition which he was to adapt many times during the course of his work in England, beginning with the portrait of Archbishop Warham himself.

On the left is a faint outline drawing of the head of Erasmus, on the right a detailed study of the right hand, unique in Holbein’s surviving work. Both are evidently part of the preparation for Holbein’s portrait of Erasmus dated 1523 (shown left). Holbein followed the study of the hand closely in the painting but made a series of alterations to the length of the thumb during its preparation. These adjustments were probably required as a result of the slightly higher viewpoint Holbein chose for the painted portrait.

According to an old inscription on the reverse, this small image of Erasmus was owned by John Norris who gave it to Edward Banister, both of whom held positions at the court of Henry VIII; Norris (about 1502–77) was a Gentleman Usher of the Privy Chamber by 1536.

The image was evidently developed from the three-quarter portrait Holbein made in 1523 (shown nearby), and the supply of such images by Holbein to admirers of the great humanist is documented in contemporary correspondence.

In this preparatory study for the painting of 1527 now in the Louvre, Holbein, as in other such portrait drawings, defines only the head and shoulders of his subject, who had been Archbishop of Canterbury since 1504.

The direct, slightly upward glance animates the study, which, like the image of the Archbishop’s friend Erasmus, is an unsparing study of old age.

Warham, who supported Erasmus’s scholarship, had Holbein paint him in a composition which mirrored that of the portrait of Erasmus Holbein had made in 1523 to send to Warham (shown right).

This drawing has been cut down and the paper used was presumably originally similar in size to the sheet on which Lady Guildford is drawn. Little indication is given of the portrait composition beyond head and shoulders, but Holbein notes a position for the staff lower right, and with parallel lines sketches the position of the collar of the Order of the Garter.

The drawing shows a man with a slightly fatter face than in the painting (below), and it seems possible that Guildford instructed Holbein to make his face appear somewhat slimmer.

In this study from life for the painted portrait of 1527 (St Louis Museum of Art), Lady Guildford smiles, glancing almost flirtatiously towards her husband, Sir Henry Guildford, whom she married in 1525 (above).

Holbein uses red chalk with great subtlety to suggest the plumpness of her mouth, varying the depth of shading from the strong red of the left hand side to the lighter, cushioned effect of the lower lip, where the chalk diminishes to form a highlight.

Guildford (1489–1532), bulky and magnificent in costly cloth of gold, is presented with the attributes of power and success: the collar and badge of the Royal Order of the Garter, to which he was elected in 1526, and the white staff of the important post of Controller of the Household. On his hat he wears a fashionable badge depicting surveying instruments and a clock.

Holbein used the motif of an imaginary plant seen in the background in several other English portraits, its leaves decoratively combining fig leaves and fruit with vine tendrils.

The costly dress and jewels worn by this unidentified couple suggests they are English courtiers.

According to Holbein’s annotations, the flap of the woman’s headdress is red, the back yellow; her upper sleeve is white and the edge of her square neckline is of silk. Her lips are given their distinctive shape with red chalk, but elsewhere in both drawings the modelling of the face has been lost and the outlined features stand out disproportionately. These outlines were traced over with a stylus, to prepare the drawings to be transferred to panels for painted portraits, which do not survive.

The sitter has been plausibly identified as Anne Ashby, wife of Sir Francis Lovell (died 1551) of East Harling, Norfolk, an Esquire of the Body to Henry VIII. Squirrels appear on the Lovell family coat of arms; thus the bright-eyed, chained red squirrel, which nibbles on a nut, is not only a representation of a family pet but also serves to identify the family heraldry. The starling may be a punning reference to the family seat at East Harling.

The portrait was perhaps commissioned in celebration of the birth of the Lovells’ son in spring 1526.

Thomas Godsalve (about 1481–1545) was a prosperous Norfolk landowner and registrar of the Consistory Court at Norwich, ambitious for the career of his son John (about 1510–1557/8).

This unusual composition, the father placed in front of the son, suggests the hierarchical representations of tomb sculpture and memorial paintings. But this formality is offset by Holbein’s careful characterisation of both men and the precise placing of their heads, as well as by the way they are positioned behind the desk with its beautifully detailed inkwell and pencase.

This unique compositional drawing records Holbein’s design for a lost life-size group portrait of Sir Thomas More and his family, painted on linen cloth. It documents the changes More told Holbein he wished to incorporate: he preferred his wife on the far right to sit, not kneel and asked that musical instruments should be added to the sideboard.

The inscriptions identifying the subjects were made by Holbein’s associate, the royal astronomer Nikolaus Kratzer, evidently in preparation for making a gift of the drawing to More’s great friend Erasmus.

This is one of two individual portrait drawings Holbein produced of Sir Thomas More (1477/8–1535), then Chancellor of the Duchy of Lancaster and a judge in Star Chamber. This large drawing is on the same scale as the painting in the Frick Collection, New York.

Unusually for Holbein, its outlines are pricked for transfer, following closely details such as the iris and tear ducts, but these outlines appear to have been adjusted slightly in the creation of the portrait. It is not clear if Holbein also used this drawing in creating the group portrait.

At the time of Holbein’s first visit to England, the lawyer Sir John More, father of Sir Thomas More, was aged about seventy five. He is shown in the group composition at the centre of the family in his judge’s robes, but here wears a fur-lined gown.

The drawing demonstrates Holbein’s great facility with chalk and his variation of touch, from the quick zigzags of the fur to the softness of hair and eyebrows. Subtle shading in red and black suggests the sagging flesh around the deep eye-sockets and cheekbones.

John More (1508–1547) was the only son of Sir Thomas More; he married Anne Cresacre in 1529. After More’s execution he was briefly imprisoned in the Tower. In the drawing for the group portrait John is shown standing bare-headed in the background of the composition, next to his wife.

Here Holbein makes unusually free and vigorous use of black chalk for the swift, almost jagged outlining of the hand and wrist and for the slashing diagonals of the shiny striped sleeves.

Anne Cresacre (1511–77) became Sir Thomas More’s ward as a baby, after the death of her father in 1512, and in 1527 was betrothed to More’s son John; they married in 1529.

In this drawing she is shown seated in a chair, the struts of its back clearly visible. However, in the preparatory drawing for the group portrait Holbein shows her standing, at the same level as other standing figures in the back row, and the chair back has been removed.

Cecily Heron (born 1507) was Sir Thomas More’s youngest daughter and married to Giles Heron, who was hanged for treason in 1540. In the group portrait she is shown with her arm across her body in a pose resembling Leonardo da Vinci’s portrait of Cecilia Gallerani, now in Cracow, Poland. This pose, which Holbein presumably derived from a copy, serves partially to mask Cecily Heron’s pregnancy, made visible here by the manner in which her lacing is let out across her body.

Elizabeth Dauncey (born 1506) was the second daughter of Sir Thomas More. In 1525 she married William Dauncey; a Knight of the Body and Privy Councillor to Henry VIII.

The inscription is one of the small number later added to Holbein’s English portrait drawings which are demonstrably false, since this drawing is clearly a study for the portrait in the family group, where Elizabeth Dauncey is identified by Nikolaus Kratzer.

Holbein has indicated by a note that part of her bodice is to be ‘red’.

Margaret Giggs (died 1570) was Sir Thomas More’s foster daughter, and in 1526 married her tutor, John Clement, soon to be a court physician. In the drawing for the group the woman named Margaret Giggs leans towards John More and wears a different headdress. However, in a copy of Holbein’s lost painting, she is shown with the fur hat and upright pose of the present drawing, suggesting Holbein made this drawing to reflect a further amendment to the composition requested by More.

The drawing is wrongly inscribed ‘Mother Iak’.

In spring 1527 Holbein spent several weeks executing a painting of the map of the world. It formed the ceiling of a theatre at Greenwich Palace where Henry VIII entertained a French embassy in May.

He worked in collaboration with the Royal Astronomer Nikolaus Kratzer and the resulting scene, which, with theatrical sleight of hand, incorporated scenes of the ‘earth environed by the sea’ as well as the heavens, may have had some resemblance to this woodcut. This design itself may have been carried out in collaboration with Kratzer.

In 1527 Holbein painted the English defeating the French at the battle of Thérouanne in 1513 for the reverse of a triumphal arch in the dining hall at Greenwich Palace. He was paid for a ‘plat’, which suggests a map or aerial view, rather than this energetic criss-crossing of radiating pikes arranged around the central struggling pair.

The function of this vigorous drawing with its strong sense of diagonal movement is unknown, but its style suggests it may date from Holbein’s stay in France in 1524.