His contact book boasted the name of one of the leading European scholars of the day, Desiderius Erasmus – Holbein had produced a set of illustrations for his philosophical work, In Praise Of Folly. Not only that, but he had illustrated Martin Luther’s German translation of the Bible.

When Erasmus gave Holbein a letter of introduction to Sir Thomas More before he made a trip to England in 1526, he found himself on the fringes of the Royal Court. Invited to live with the Mores in Chelsea, he painted a series of portraits of the future Lord Chancellor, including one of More with his family. After a productive and profitable two years, Holbein returned to Basel, and his wife and family.

Things were changing back at home, though. Following the Lutheran revolution in spiritual matters, the Reformed Church was beginning to impose restrictions on what subjects artists could paint and after a few years Holbein decided to head once again for the more congenial atmosphere of England. It was a hard decision, because he had to leave his family behind again.

London had changed too while he had been away. Thomas More was now out of favour for not accepting the King’s divorce from his first wife, Catherine of Aragon, and would eventually lose his head. Holbein found his skills were still in demand, not least by the King’s new favourite, Anne Boleyn. He designed a triumphal arch for Anne’s coronation in 1533, and by 1536 had entered the service of Henry himself.

A man of many talents

We shouldn’t think of Holbein only as a painter – his handiwork was spread throughout the royal households (read more about Holbein here). He was the probable designer of a table fountain set with rubies, diamonds and pearls, which gushed water from the breasts of three naked figures at its base, which Anne Boleyn presented to Henry as a New Year gift in 1534.

Holbein also, of course, produced many portraits of the King. Even though he was now into his forties and had lost a little of the famous glow of his youth, Henry was struck by the air of authority that radiated from Holbein’s portraits of him. This was a King, after all, who had stood up to the full wrath of papal authority and won – the first monarch in English history to be addressed formally as “Your Majesty”.

Henry used his portraits much as a publicist would today. They were sent out to people he wanted to cement diplomatic alliances with, while members of his court bought copies to demonstrate their allegiance at a time when several of the King’s advisors were beginning to have grave doubts about the course of his policies.

Picture perfect

Holbein’s masterpiece was the first officially commissioned State portrait of any British sovereign.

While copies were widely distributed as a matter of deliberate policy, they were also in popular demand. This ensured that, more than any other King before him, Henry VIII was a visual image, not just an abstract idea, in his subjects’ minds. Find out more about the Holbein's portrait here.

Art critic Jonathan Jones, writing on the portrait in The Guardian in 2003, said: “Holbein's Henry VIII is Carnival, triumphing over Lent. He is the Lord of Misrule and he is Hercules. Whatever he is, he is not quite human. Hans Holbein the Younger single-handedly made Henry VIII and his court the first British people we can picture clearly in our minds.”

No oil painting

Like many of the King’s favourites, Holbein eventually lost his approval.

In 1539, Henry commissioned him to go to Düren in Germany and paint the portrait of Anne of Cleves, so that he could see whether she was suitable marriage material. It had been a couple of years since the death of Jane Seymour, and the result looked promising enough.

Once Anne arrived in England, however, the King was unimpressed. On the eve of his wedding, he discovered his wife-to-be was, as he put it, a “fat Flanders mare”, and blamed Holbein for producing the misleading portrait.

The marriage lasted barely six months, before Anne was shunted aside into a reasonably well-to-do house in Lewes, Sussex, where she contentedly outlived the King.

Plague victim

After some years in the official wilderness, Holbein’s reputation in the court was gradually restored.

Shortly before his death, he produced a set of miniatures of all three of Henry’s offspring – Mary, Elizabeth and Edward – at Henry’s sixth and last wife Katherine Parr’s request.

Holbein died of the plague in the autumn of 1543, leaving a final work depicting Henry presenting a charter to the Barber Surgeons’ Company unfinished. He was to prove an irreplaceable loss. Nobody of his talent was to emerge again at the English court until van Dyck’s appointment as royal portraitist to Charles I in the 1630s.