The Virgin and Child with St. Anne is an oil painting by Leonardo da Vinci depicting St. Anne, her daughter the Virgin Mary and the infant Jesus. In 1498, Leonardo probed into incorporating the three figures together by drawing the Burlington House Cartoon , which included all three figures in addition to an infant St. John. the Baptist. The cartoon would never materialize into a painting, but the "The Virgin and Child with St. Anne" would emerge.

Leonardo painted "The Virgin and Child with St. Anne" during the later years of his life when he was occupied with an interest in mathematics and other pursuits. The demands of his other interests may have forced him to leave his painting incomplete.

Sigmund Freud undertook a psychoanalytic examination of Leonardo in Leonardo da Vinci, A Memory of His Childhood . According to Freud, the Virgin's garment reveals a vulture when viewed sideways. Freud claims this is a manifestation of a "passive homosexual" childhood fantasy Leonardo wrote about in the Codex Atlanticus . Using Freud's translation, Leonardo recounts being attacked as an infant in his crib by the tail of a vulture. A more accurate translation is reproduced by rewording the word vulture into the word kite.