This hauntingly beautiful drawing closely relates to an oil painting on panel of the Virgin and Child with Saint Anne (Musée du Louvre, Paris) from around 1508-12, and may have been a preparatory study for it. The head seen here appears to be exactly the size of the Virgin's head in the Louvre painting. The delicately finished drawing focuses on the atmospheric dissolution of her relieflike forms, and vividly illustrates the depth of Leonardo's explorations of optical phenomena late in his career. The artist would increasingly rely on complex pictorial techniques of drawing to articulate his scientific research on the perspective of color, the disappearance of form, and the gradations of light and shadow. Here, Leonardo reworked the charcoal and black chalk drawing with red chalk, especially evident in the face (but also extending less noticeably to the locks of hair in the underdrawing), using the sfumato technique. He softly smudged all the strokes of drawing to achieve a seamlessly blended tone "in the manner of smoke" (fumo), as he called it in his notes. It conforms with the observable phenomenon of disappearing edges in the secondary planes of a perspectival space, a subject that he amply discussed in his scientific writings. Further preparatory studies for the Virgin and Child with Saint Anne composition are at the Royal Library (Windsor Castle), and these transform scientific principles into a pictorial language of magical force and nuance.

Inscription: Recto is annotated at upper left with script in pen and faded brown ink that is not legible; verso is annotated at center of right border in late Cinquecento hand (Giovanni Francesco Melzi?): ".T." and at upper center in pen and brown ink by a late Seicento hand (Sebastiano Resta?): "i20. R.Vr." (C. C. Bambach; March 26, 2006)

Marking: [obverse, lower right]: Earl of Warwick [reverse, lower right]: Sir Charles Greville, uncle of Warwick

Sir Charles Greville (British, 1763–1832); George Guy, Fourth Earl of Warwick (British, 1818–1893); Christie's, London, May 20-21,1896, no. 213.; Dr. Ludwig Mond (London, 1839–1909); Right Honorable Lady Gwen Melchett of Landford ; Sotheby's, London, May 23-24, 1951, no. 7repr. frontispiece

Winter Exhibition of Drawings by the Old Masters and Water-Colour Drawings by Deceased Artists of the British School Exh. cat., London, Grosvenor Gallery, 1877-78. Grosvenor Galleries, London, 1877-1878, cat. no. 675, p. 79.

Earl of Warwick Sale Sale cat., London, Christie's, Manson and Woods. Christie's, London, May 20-21, May 20-21, 1896, cat. no. 213, p. 26.

Bernard Berenson The Drawings of the Florentine Painters Classified, Criticised and Studied as Documents in the History and Appreciation of the Tuscan Art, with a Copious Catalogue Raisonné. 2 vols., London, 1903, vol. 2, p. 59, cat. no. vol. 2, 1045, vol. 1, p. 158.

Dr. Jean Paul Richter, London The Mond Collection, An Appreciation. 1, 2, London, 1910, fig. no. pl. 19, pp. V.2, pp. 323, ill.

Gustavo Frizzoni "La Raccolta Mond ed opere attinenti alla medesima." Rassegna d'arte. 11, no. 2, 1911, fig. no. 6, p. 43, ill.

Osvald Sirén Leonardo da Vinci. New Haven and London, 1916, p. 137.

Giovanni Poggi Leonardo da Vinci: La 'Vita' di Giorgio Vasari, nuovamente commentata e illustrata con 2000 tavole. Florence, 1919, pp. 20-21.

Frits Lugt Les marques de collections de dessins et d'estampes. Marques estampillés et écrites de collections particulières et publiques. Marques de marchands, de monteurs, et d'imprimeurs. Cachets de vente d'artistes décédés. Marques de graveurs apposées.... Amsterdam, 1921, p. 487, no. 2600.

Adolfo Venturi Storia dell'arte italiana: Vol. 9: La Pittura del Cinquecento. 9, parts 1-2, Milan, 1901-1940, fig. no. 138, p. 208, ill.

Aldo De Rinaldis Storia dell'opera pittorica di Leonardo da Vinci. Bologna, 1926, fig. no. pl. 69, p. 235, ill.

Osvald Sirén Léonard de Vinci: L'artiste et l'homme: Edition entièrement refondue et mis à jour.. 3 vols., Paris and Brussels, 1928, vol. 1, p. 112.

Bernard Berenson The Drawings of the Florentine Painters. 3 vols, amplified edition. Chicago, 1938, vol. 2, p. 116, cat. no. vol. 3, no. 1045, fig. no. vol. 3, fig. 514, vol. 1, p. 176.

Théodore Rousseau Jr. "The Metropolitan Museum of Art Bulletin" Notes. 10, December, . New York, 1951, fig. no. on cover, ill.

Marziano Bernardi Leonardo a Milano. Turin, 1952, p. 105.

"Art Treasures of the Metropolitan" A Selection from the European and Asiatic Collections of the Metropolitan Museum of Art. Art Treasures of the Metropolitan, New York, 1952, cat. no. 60, p. 68, ill.

Carlo Pedretti Documenti e memorie riguardanti Leonardo da Vinci a Bologna e in Emilia. Bologna, 1953, p. 76.

Bernard Berenson, Luisa Vertova I disegni dei pittori fiorentini. 3 vols., Revised and enlarged. Milan, 1961, vol. 2, p. 205., cat. no. vol. 3, 1049D-1, fig. no. vol. 3, fig. 499, vol. 1, p. 256., ill.

Jacob Bean, Felice Stampfle Drawings from New York Collections, Vol. I: The Italian Renaissance exh. cat. The Metropolitan Museum of Art, vol. 1, New York, 1965, cat. no. 19, fig. no. pl. 19, p. 28, ill.

Walter Vitzthum "Current and Forthcoming Exhibitions: Drawings from New York Collections." The Burlington Magazine. 108, (Feb. 1966). London, 1966, p. 109.

Walter Vitzthum "Review: Drawings from New York Collections, Vol. 2: The Seventeenth Century in Italy (Exh. cat., New York, MMA and PML, by Jacob Bean and Felice Stampfle, 1967)" Burlington Magazine. 109, April 1967. London, 1967, p. 109.

Geoffrey Agnew Agnew's, 1817-1967. London, 1967.

B. Bacall A Catalogue of the Drawings of Leonardo da Vinci and his School in the United States of America M.A. thesis, directed by Carlo Pedretti. Master's thesis, 1968 cat. no. 7.

Jacob Bean, Lawrence Turcic 15th and 16th Century Italian Drawings in the Metropolitan Museum of Art. New York, 1982, cat. no. 110, fig. no. 110, pp. 119-20., ill.

Angela Ottino della Chiesa, Mario Pomilio, L. D. Ettlinger L' opera completa di Leonardo pittore. English edition (Italian edition Milan 1967). London, 1985, p. 109.

Alessandro Vezzosi Leonardo: Arte, Scienza e Utopia Exh. cat., Toronto, J. D. Carrier Art Gallery. Toronto, 1987, p. 17.

Carlo Pedretti, Patricia Trutty-Coohill The Drawings of Leonardo da Vinci and His Circle in America. Florence, 1993, cat. no. 18, pp. 53-55.

Martin Clayton Leonardo da Vinci: A Singular Vision Exh. cat., London, The Queen's Gallery, Buckingham Palace, Mar. 1, 1996 - Jan 12, 1997. New York, 1996-1997, p. 133.

Pietro C. Marani Leonardo: una carriera di pittore. Milan, 1999, p. 288.

Pietro C. Marani Leonardo da Vinci: The Complete Paintings With an appendix of documents transcribed by Edoardo Villata. New York, 2000, pp. 288-89.

Francis Ames-Lewis "Leonardo da Vinci e il disegno a matita." Raccolta Vinciana. 29, Milan, 2001, cat. no. 23, p. 13.

Martin Clayton Leonardo da Vinci: The Divine and the Grotesque Exh. cat. Edinburgh, The Queen's Gallery, Palace of Holyroodhouse; London, The Queen's Gallery, Buckingham Palace. London, 2002, fig. no. 50, p. 149.

Leonardo da Vinci: The Divine and the Grotesque Exh. cat. Edinburgh, The Queen's Gallery, Palace of Holyroodhouse; London, The Queen's Gallery, Buckingham Palace. London, 2002, fig. no. 50, p. 149.

David Alan Brown "The Burlington Magazine" Leonardo Drawings. 114, no. 12, August. August, 2003, pp. 613-15.

Leonard de Vinci. Dessins et manuscrits Exh. cat. Paris, Musée du Louvre, May 5 - July 14, 2003. Edited by Françoise Viatte, Edited by Varena Forcione, Musée du Louvre, Paris, 2003, p. 261.

Leonardo da Vinci, Master Draftsman Exh. cat., New York, The Metropolitan Museum of Art, January 22 - March 30, 2003. Edited by Carmen C. Bambach, The Metropolitan Museum of Art, Yale University Press , New Haven and London, New York, 2003, cat. no. 108, fig. no. 35a,b,c,d, pp. 41-48, 566-5, ill.

Giovanna Giacobello Bernard (ed.) Leonardo da Vinci: Capolavori in mostra Exh. cat., Turin, Biblioteca Reale, 2006. Milan, 2006, cat. no. I.15., pp. 64-67.