Hans Holbein le Jeune

In 1539 Henry VIII sent his court painter to Duren, in the German duchy of Cleves, with one job: paint an honest likeness of Anne, the duke's sister and a candidate for the king's fourth wife. Hans Holbein the Younger had been King's Painter since around 1535, producing portraits, jewelry designs, and festival decorations for the Tudor court, and his word on Anne's appearance was about to matter more than any ambassador's report.

Henry liked what he saw and agreed to the marriage. When Anne arrived in England in January 1540 and the king met her in person for the first time, he was reportedly startled to find her taller and heavier-featured than the portrait suggested, and the marriage was annulled within six months. Whether Holbein flattered her or simply painted what convention demanded, historians still argue, but the portrait had already done its diplomatic work.

Holbein had built his English career two decades earlier on a letter of introduction from Erasmus, the Rotterdam scholar, which got him into the household of the statesman Thomas More. He died in London in 1543, most likely of plague, having spent his final years turning out roughly 150 portraits of Tudor royalty and nobility.