This solemn, almost austere portrait is of Christina of Denmark, Duchess of Milan, then 16, whom Holbein met in Brussels in March 1538. He was sent there especially to draw her because the King was looking for a wife and wanted someone whose looks appealed to him. On 12 March at one o’clock in the afternoon, Holbein was conducted to the duchess’s presence, and she sat for him for ‘but thre owers space’. She was at the time in mourning for her first husband, the Duke of Milan, hence the widow’s weeds.

The King was delighted by the result, so much so, that an ambassador to the Court of Saint James reported that “since he saw it he has been in much better humour than he ever was, making musicians play on their instruments all day long.” Such was the power of Holbein’s art.

However, the political negotiations broke down and the marriage never took place. Instead, Henry married “the Flanders Mare”, Anne of Cleves – whom Holbein also painted beforehand. Meanwhile Christina said that, had she possessed two heads, she would willingly have put one at the disposal of the King of England. He never parted with this portrait, dreaming, no doubt, of what might have been.

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You’re looking at the only definitive portrait of Henry VIII. By definitive I mean that this is the only image of the king that we know to be just one step removed from a drawing done by Holbein from life. So, given Holbein’s breathtaking ability to capture a likeness, we can be confident that this really is how the King looked in 1537 or thereabouts, when this painting was made.

Henry is already portly but he’s intimidating nevertheless. He’s confident, wary, and at the height of his powers. The portrait stresses the King’s importance, chiefly by dressing him in a magnificent costume of silver and gold. Even his shirt collar is embroidered with gold thread. Holbein actually used powdered gold in his paint, and for the background he used the expensive ultramarine pigment, made from rare, semi-precious stone lapis lazuli. The result is a portrait like a religious icon. After all, though Henry was a man – we feel he must have looked exactly like this – he was also an all-powerful monarch and the supreme head of the Church of England. Significantly, he was the first English monarch to be addressed as ‘Your Majesty’, rather than ‘Your Grace’. English kings and queens have been ‘Your Majesty’ ever since.

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Everyone who saw one of Holbein’s portraits was amazed at its lifelike qualities, and this portrait of someone called Robert Cheseman shows us why. It’s not just the face, which is both a physical likeness and an examination of character. It’s also the depiction of such contrasting textures as those of fur, silk and leather, and also the feathers on the bird perched on Cheseman’s glove.

Holbein was not yet Court painter, but that didn’t mean he wasn’t painting people, both major and minor, at Court. Robert Cheseman was one of the major figures working for Henry VIII. To begin with, he was the King’s representative in Middlesex, and he raised troops there, whenever required. Later, seven years after this painting was finished, Cheseman was sent to receive Anne of Cleves on her arrival in England in 1540, prior to her marriage to King Henry. You might think, from the presence of the bird that Cheseman was the King’s falconer, a significant social position then. But we know for sure that he wasn’t. A bird of prey was an expensive luxury at the time, and falconry itself was a pursuit reserved for the upper classes. So Holbein may simply have included the bird to suggest Cheseman’s rank. As so often, the inscription gives the subject’s name and age – Cheseman was 48 at the time – as well as the date, 1533.

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