Leonardo da Vinci (1452–1519) frequently recorded his ideas and observations in notes and sketches, regardless of subject matter. More of Leonardo’s drawings have survived than those by any other artist of the Italian Renaissance. Dian Woodner, who has donated many works over the years to the National Gallery of Art, has now given the museum Leonardo’s Grotesque Head of an Old Woman (1489/1490), one of a series of some 30 studies, identical in small format, style, and technique.

These drawings represent Leonardo’s most sustained exploration of human physiognomy. Drawing as a system for studying nature and preparing other works of art—as the most basic system of representation in the Western tradition—was barely a generation old when he made these drawings, between c. 1495 and 1506/1508. Leonardo, who owned the principal early treatises on physiognomy and wrote about it in his notebooks, was the first artist to take that system beyond ideal types. He used it to attempt the most minute physical variations and to reach beyond surface appearance to evoke personality and convey character.

Like the other imaginary heads, this drawing appears to have been a stand-alone exercise. It helped to prepare and inform the unprecedented range and subtlety of human expression in Leonardo’s paintings. His Milanese followers would take these studies literally. This old woman appears in several contemporary copies—the National Gallery possesses one by Francesco Melzi, Leonardo’s closest follower—and as a new type in various paintings, even north of the Alps. The influence of these drawings never waned in European art, inspiring all later physiognomic studies and laying the foundation of caricature, which flourished in 18th-century England.

Imaginary but utterly individual, this woman is an exquisite example of this type of drawing. It depicts the head and bust of an aged woman with an elaborate coiffure and wearing a small tiara. Her physical peculiarities are pronounced, and she is emblematic of the ravages of time and the fading of physical beauty. Leonardo uses a few strokes of the pen to suggest the shriveled skin, the low and receding forehead, as well as the small aquiline nose, while the lower lip and chin are almost nonexistent. The lines that describe the small folds in the upper lip, nearly imperceptible, indicate the lack of teeth. The curved but wavering lines that describe the woman's shapeless bosom, complete with a carnation inserted in the laced-up bodice of the dress, are echoed by the opposing curve of her back, resembling a small hump.

This drawing also reflects Leonardo's interests in "jests" and "puzzles," consistent with a taste for visual and verbal play at the Sforza court in Milan, with which Leonardo was associated for 17 years. The frequency with which he drew grotesque heads is inspired by his continuous research of the monstrous, the astounding, and the unusual—alongside his pursuit of the beautiful and the sublime. These two contrasting aspects coexisted in the mind and work of Leonardo and constitute two of the major spheres around which his studies turned. This woman’s fallen chin and exaggerated scowl could be the stuff of crude humor. But the dignity of her pose, held firm in the profile of official portraiture, the touching accent of the carnation at her breast, and what seems a self-possession in the eye elevate her toward a complete being, of distinct form and inseparable being. This is the first time in the history of art that an individual existence is rendered so attentively and completely.

This group of drawings comes down directly from Leonardo’s studio with an uninterrupted and very distinguished provenance. The group was in the possession of the dukes of Chatsworth by 1723. This drawing is one of four that were sold at Christie’s, London, in 1984. One was acquired by the Getty, two by a private collector in New York, and this one by Ian Woodner, who assembled an extraordinary collection of over 1,000 old master and modern drawings, making him one of the 20th century's most important collectors. More than 150 works from his collection now reside at the National Gallery. While Woodner gave some works himself in the 1980s, the majority have been donated by his daughters, Dian and Andrea, both of whom have also made other gifts and have pledged works from their personal collections.

The drawing has been on deposit at the National Gallery since it was exhibited in 1999 and was pledged by Dian in 2017. It becomes the National Gallery’s second Leonardo drawing, joining a sheet of studies acquired with Armand Hammer’s collection in 1991. There are just nine other Leonardo drawings in American public collections: in addition to those from the Chatsworth sale, one more at the J. Paul Getty Museum, one at the Morgan Library and Museum, and six at the Metropolitan Museum of Art.

Grotesque Head of an Old Woman has been included in several exhibitions held at the National Gallery, including: The Touch of the Artist: Master Drawings from the Woodner Collections (1995–1996); Art for the Nation: Collecting for a New Century (2000–2001); Master Drawings from the Woodner Collections (2006); Arcimboldo, 1526–1593: Nature and Fantasy (2010–2011); and The Woodner Collections: Master Drawings from Seven Centuries (2017).

The National Gallery is the home of Leonardo da Vinci's haunting and hypnotic masterpiece, Ginevra de' Benci (c. 1474/1478), the only painting by the master in the Americas.