The Strangest Portraits in Art History

Artists have always had vivid imaginations, but for a very long time most works were commissioned, leaving little room to stray from a patron's wishes — usually to be shown at their most flattering. Yet when artists did stray, they did not do so by halves. We present five famous, critically acclaimed portraits that will truly make you doubt your own eyes.
1. The Ugly Duchess

Quentin Matsys, "An Old Woman (The Ugly Duchess)", 1531, photo Wikimedia Commons
No one who sees this painting can look away. For decades, scholars believed it was a satire. The woman sitting before us is dressed as an aging seductress. In her hand she holds a rose bud, charged with sexual metaphor, a plunging neckline exposes her wrinkled bosom, and her heart-shaped headdress resembles a pair of horns. All of this points to bodily temptation. The clothing and jewelry chosen by the artist mark the woman as belonging to the upper class, yet by the time the painting was made, such fashions were already a good century out of date. The portrait would seem intended to mock an ugly old woman for her wanton behavior.
Yet thanks to science, we now know the truth is somewhat different. New research has revealed that the woman depicted actually suffered from an advanced case of Paget's disease, which deforms the bones. This is reflected in her unnaturally curved nostrils, hooked nose, protruding upper lip, and enlarged collarbones and forehead. Shame on your own indecent thoughts!
2. Medusa

Michelangelo Merisi da Caravaggio, "Medusa", 1593, photo Wikimedia Commons
Before your eyes is the severed head of a monster! You probably know Medusa as a beautiful woman with living snakes in place of hair, able to turn a man to stone with a single glance. And so she was, until Perseus, using the shield lent to him by Athena, cut off her head.
This painting is strange in more ways than one — for a start, Caravaggio's model was a young man, and the work itself was painted on an actual shield, yet strangest of all is the moment from the myth that the artist chose to depict.
According to the myth, the mirrored shield entrusted to Perseus not only let him see Medusa's reflection, but also gave her one last chance to see herself. It's safe to bet that, seeing her own head severed from her body, her final moment of self-reflection did not bring the most pleasant thoughts. Yet Caravaggio's work, disturbing as it is, offers a striking rendering of the last moments of Medusa's life.
3. Gabrielle d'Estrées and One of Her Sisters

Unknown artist, "Gabrielle d'Estrées and One of Her Sisters", c. 1594, photo Wikimedia Commons
Bathing with one's siblings is usually considered acceptable only in early childhood — beyond that it simply seems too strange — yet at first glance, this painting suggests otherwise. The outstretched hand of her sister, the Duchess of Villars, pinching a nipple, raises doubts about the propriety of the bath, while the raised curtain makes viewers feel like intruders.
Fortunately, art historians assure us we should banish all such shameful thoughts. The woman on the right, Gabrielle, was the mistress of King Henry IV, and scholars believe her sister's gesture indicates that Gabrielle is expecting the king's illegitimate son. Strange as it may seem, the pinched nipple here is a symbol of fertility. The theory is further supported by the figure in the background, seen sewing infant's clothes.
4. The Hairy Man

Unknown artist, "Portrait of Petrus Gonsalvus", 1580, photo Wikimedia Commons
Undoubtedly one of the stranger exhibits in today's collection. Petrus Gonsalvus, the "man of the woods," was born in Tenerife in 1537, and his life has been widely documented, as he became famous for a condition called hypertrichosis, which causes excessive body hair growth. Although his contemporaries never fully regarded Petrus as human, he was ennobled, married, had children (four of his seven also had hypertrichosis), and painted. It is thought that the marriage of Petrus Gonsalvus and Lady Catherine inspired the tale of "Beauty and the Beast."
5. The Ballet of the Horsemen

Jan Thomas, "Prince Gundakar in a Fantastic Costume", 1667, photo Wikimedia Commons
Yes, you heard that right — a ballet on horseback, and there is evidence that Prince Gundakar himself took part in it. The lavish event was held at the Viennese court to mark the marriage of Emperor Leopold I and Margaret Theresa of Spain (the very same subject of Velázquez's most famous portrait). The strangest part is how the poor horse managed to carry all that finery — judging by appearances, it can't have been easy.