This must be one of the most arresting faces in the National Gallery’s Collection. An elderly woman with lively eyes set deep in their sockets, a snub nose, wide nostrils, pimply skin, a hairy mole, bulging forehead and a prominent square chin and rests one hand on a marble parapet. Her neck is rumpled by age and she seems to have lost all her teeth. She challenges every traditional canon of beauty. This striking work captures the emergence of the grotesque (in the original sense of the word, denoting the surprising, unusual, and playful) as a subject for painting. Quinten Massys pioneered this type of secular, satirical imagery.

The woman’s clothes are rich. Defying the modesty expected from older women during the Renaissance, she is wearing a low-cut, uncovered, and tightly laced bodice that emphasises her wrinkly cleavage. Her hair is concealed in the horns of a heart-shaped bonnet, over which she has placed a white veil, secured by a large, bejewelled brooch. However fine her attire, by the time this panel was painted in the early sixteenth century her clothes would have been many decades out of date, prompting laughter rather than admiration. Her headdress had by then become an iconographic shorthand for female vanity, its horns compared to those of the devil.

This painting is part of a pair: her ‘other half’, An Old Man also painted by Massys, is in a private collection in New York. The old woman dons this flamboyant and provocative outfit in order to seduce the old man, to whom she offers a rosebud, a flower with sexual connotations. She breaks conventions by appearing on the proper right, the more prestigious side reserved for men in double portraits. Viewers were invited to mock the foolishness of the old who behave as if they are still young.

There has been speculation that the artist depicted a woman with Paget’s disease – a rare illness causing bone hypertrophy. Yet rather than painted from life, this figure was more probably a fictional, folkloric character from the world of carnival: the figure of the lavishly dressed old woman with a horned headdress recurs in several prints, miniatures, and misericords (the carved reliefs that adorned the underside of folding seats in choir stalls) of the period. In presenting such figures of fun as elaborate portraits, Massys parodied the dignified genre.

Massys shared his interest in the expressive power of the human face with his contemporary, Leonardo da Vinci, who made countless studies of grotesque heads, many of which feature old women in similar attire. Two drawings of an old woman by followers of the artist show the same unforgettable face (Royal Library, Windsor Castle and New York Public Library). Massys probably took inspiration from Leonardo’s composition, as he did on other occasions. Yet he adeptly transformed the small drawing into an ambitious life-size painting, giving it a pendant and fleshing out its satirical content.

Technical analysis confirms that the painting is an original, not a copy. infrared reflectograms have revealed a good deal of underdrawing. That for the face is carefully done, whereas that for the clothes and other elements is freer and sketchier. For the face, the artist may have carefully followed a preliminary drawing but made several changes. The eyes were drawn twice – they were moved slightly up and to the right – and the painted chin, neck and right ear are smaller than in the underdrawing. Her right shoulder was also redrawn in its present painted place and both hands are differently posed.

Several idiosyncrasies of the painting technique support attribution to Massys himself. The paint is worked in many places wet-in-wet and has been dragged and feathered. In many places energetic feathering has been used to soften transitions of tone, a technique which seems to have been peculiarly Quinten’s. Some of the hair near the Duchess’ right ear and some of the embroidery on her right cuff are rendered in sgraffito, where the artist has scratched through a layer of still-wet paint to reveal what is underneath. The mottled areas of her flesh were achieved by spotting the basic pink with red and white dots, dashes and blotches. The skill of the brushwork is clear if you look very closely at the filigree of the brooch, where at least five shades of brown, orange, pink and yellow are found, and where a paint containing mainly lead-tin yellow is fairly heavily impastoed.

The two horns of the headdress were rendered by different methods. On the right, the horn’s stripes have been made by removing the red, white and blue to reveal the black layer underneath; on the left, black paint has been applied on top. They may have been done by different assistants, or perhaps Massys discovered another way of executing the patterns which he preferred to the first.

In the seventeenth century, the painting was misidentified as a portrait of Margaret Maultasch, Duchess of Carinthia and Countess of Tyrol, a historical figure who had been defamed by her enemies as the ‘ugliest woman in history’. On this basis, she later gained the nickname ‘The Ugly Duchess’. In the Victorian era, this picture (or one of its many versions) inspired John Tenniel's depiction of the Duchess in his illustrations of Lewis Carroll’s Alice’s Adventures in Wonderland (1865). This entrenched the moniker and turned this figure into an icon for generations of readers.

Style: High Renaissance