By Maria Bregman
Hans Holbein the Younger was not only a brilliant painter, but also a savvy matchmaker. The German artist, who served as the official court painter for Henry VIII and his wives, was responsible for creating the portraits that the king used to choose his future spouses. Holbein’s portraits were the equivalent of a 16th-century dating app, allowing Henry to swipe left or right based on the appearance and status of the women.
Holbein’s role as a matrimonial agent began in 1539, when Henry was looking for a fourth wife after the death of Jane Seymour. The king had two options: Anne of Cleves, the sister of the Duke of Cleves, a German ally; or Christina of Denmark, the widow of the Duke of Milan, a potential ally against France. Holbein was sent to paint both women and bring back the portraits for Henry to inspect.
Holbein’s portrait of Anne of Cleves was flattering and elegant, showing her in a rich dress and jewels, with a serene expression and a hint of a smile. Henry was impressed by the portrait and agreed to marry her. However, when he met her in person, he was disappointed by her appearance and demeanor, and famously called her a “Flanders mare”. He annulled the marriage after six months and paid her a generous settlement to avoid a diplomatic crisis.
Holbein’s portrait of Christina of Denmark was equally stunning and captivating, showing her in a black mourning dress and a white ruff, with a melancholic gaze and a delicate hand. Henry was enchanted by the portrait and proposed to her, but she refused, saying that she had only one head and wanted to keep it. She was referring to the fate of Henry’s second wife, Anne Boleyn, who was beheaded on charges of treason and adultery.
Holbein’s portraits of Henry’s wives and potential wives were not only artistic masterpieces, but also political tools. They shaped the image and identity of the Tudor dynasty, as well as the perception and representation of the women themselves. Holbein’s portraits influenced the historical and cultural memory of these figures, as well as the literature and media that were inspired by them, such as Hilary Mantel’s Wolf Hall and its BBC adaptation.
Holbein’s portraits also reveal the artistic and political challenges that he faced in his career. He had to balance the demands and expectations of his patrons, the realities and limitations of his subjects, and his own artistic vision and style. He had to create portraits that were accurate and flattering, but also expressive and compelling. He had to navigate the complex and turbulent court of Henry VIII, where favor and fortune could change in an instant. He had to survive the religious and social upheavals of the Reformation, which threatened his livelihood and safety.
Holbein was a remarkable artist who left a lasting legacy in the history of art and the history of England. His portraits of Henry VIII and his wives are among the most iconic and influential images of the 16th century, and they continue to fascinate and intrigue us today.

Hans Holbein the Younger, Anne of Cleves, 1539, oil on parchment mounted on canvas, 65 x 48 cm, Louvre Museum, Paris. (Photo by Wikipedia Common)





