Why Leonardo da Vinci’s Greatest Painting is Not the Mona Lisa

Despite cre­at­ing two of the most famous paint­ings in the his­to­ry of West­ern art, The Last Sup­per and the Mona Lisa, Leonar­do da Vin­ci did not par­tic­u­lar­ly think of him­self as a painter. Sig­mund Freud may have devot­ed sev­er­al hun­dred words to show­ing that the Renais­sance man par excel­lence rarely fin­ished an art­work because of infan­tile psy­cho­sex­u­al con­flicts, but it seems more fit­ting to look at Leonardo’s approach to paint­ing as of a piece with his approach to every­thing: He was sim­ply far more inter­est­ed in process than prod­uct. Even when the prod­uct was a mas­ter­piece-in-the-mak­ing, and Leonar­do’s patrons await­ed, the artist’s rest­less mind was ready to move on before he fin­ished a com­mis­sion.

Such was the case with the Mona Lisa, which Leonar­do nev­er deliv­ered to his client and instead brought with him to France. This paint­ing, in all its unfin­ished mys­tery, may be Leonardo’s best-known work, but it is not — as Evan Puschak, a.k.a. The Nerd­writer, argues above — his best.

That hon­or should be reserved for a paint­ing Leonar­do began in the same year as the Mona Lisa, 1503: The Vir­gin and Child with St. Anne, which he worked on for sev­en years, nev­er deliv­ered to his client (most like­ly the King of France), and left unfin­ished at the time of his death in 1519.

The paint­ing depicts a group­ing of three fig­ures: the infant Christ, wrestling a lamb, his moth­er, attempt­ing to pull him away, and her moth­er, the apoc­ryphal St. Anne, form­ing the sta­ble base and apex of the tri­ad. Behind her head tow­ers a dense moun­tain range, a sym­bol of deep eco­log­i­cal time, says Puschak, just as the lamb in the fore­ground sym­bol­izes the Pas­sion to come. This tran­si­tion from a pre-his­toric past (one far more ancient than the Bib­li­cal sto­ries) to a redeemed future does not ter­mi­nate with the lamb, says Puschak, but with us, the view­er.

The pyra­mi­dal com­po­si­tion recalls Leonardo’s The Vir­gin of the Rocks from 1483. Such group­ings were com­mon in ear­ly Renais­sance paint­ings, but The Vir­gin and Child with St. Anne rep­re­sent­ed a mas­ter­ful refine­ment of the com­po­si­tion and of Leonar­do’s famed sfu­ma­to tech­nique. As Art­dai­ly notes:

In Flo­rence, where it was con­ceived, the Saint Anne quick­ly drew con­sid­er­able atten­tion and can be seen as a water­shed moment in the evo­lu­tion of artis­tic lan­guage, inspir­ing many dis­ci­ples and col­leagues who sought to emu­late Leonar­do’s style and tech­nique in this work. Flo­ren­tines were fas­ci­nat­ed by the var­i­ous car­toons exe­cut­ed by Leonar­do and by the paint­ed work, even in its rough out­lines.

One prepara­to­ry work, the so-called “Burling­ton House Car­toon” (below), shows “the full expres­sion of Leonar­do’s first vision of the Saint Anne theme upon being award­ed the com­mis­sion.”

Image via the Nation­al Gallery

The work also shows the con­tin­ued devel­op­ment of a theme that absorbed the artist through­out his life, expressed in ear­li­er works such as The Vir­gin and Child with Cat and The Vir­gin of the Rocks. “These Vir­gin and Child com­po­si­tions tes­ti­fy to Leonar­do’s ques­tion to ren­der in the most com­pelling man­ner the ten­der­ness of the rela­tion­ship between Jesus and the Vir­gin Mary,” and thus, between moth­er and son. Most of Freud’s obser­va­tions in his Leonar­do essay are non­sense, based on a mis­trans­la­tion into Ger­man of the word “vul­ture” for a word that actu­al­ly means “kite” (an error he lat­er found par­tic­u­lar­ly embar­rass­ing). But his dis­cus­sion of Leonar­do’s child­hood and his best, unfin­ished paint­ing may strike us with par­tic­u­lar poignan­cy.

[T]he smile which is play­ing on the lips of both women, although unmis­tak­ably the same as in the pic­ture of Mona Lisa, has lost its sin­is­ter and mys­te­ri­ous char­ac­ter; it express­es a calm bliss­ful­ness.… Leonardo’s child­hood was pre­cise­ly as remark­able as this pic­ture. He has had two moth­ers, the first his true moth­er, Cate­ri­na, from whom he was torn away between the age of three and five years, and a young ten­der step-moth­er, Don­na Albiera, his father’s wife. By con­nect­ing this fact of his child­hood… and con­dens­ing them into a uni­form fusion, the com­po­si­tion of Saint Anne, Mary and the Child, formed itself in him.

Per­haps Freud was right, and The Vir­gin and Child with St. Anne was tru­ly Leonar­do’s most per­son­al work, the apoth­e­o­sis of a quest to inte­grate his per­son­al­i­ty through art. What­ev­er the case, we can say, along the psy­cho­an­a­lyst, that “on becom­ing some­what engrossed in this pic­ture it sud­den­ly dawns upon the spec­ta­tor that only Leonar­do could have paint­ed this pic­ture.”

On a side note, Nerd­writer, the cre­ator of the video above, has a new book com­ing out, Escape into Mean­ing: Essays on Super­man, Pub­lic Bench­es, and Oth­er Obses­sions. You can pre-order it now.

Relat­ed Con­tent:

Leonar­do da Vinci’s Note­books Get Dig­i­tized: Where to Read the Renais­sance Man’s Man­u­scripts Online

Leonar­do Da Vinci’s To-Do List from 1490: The Plan of a Renais­sance Man

How Leonar­do da Vin­ci Made His Mag­nif­i­cent Draw­ings Using Only a Met­al Sty­lus, Pen & Ink, and Chalk

Josh Jones is a writer and musi­cian based in Durham, NC. Fol­low him at @jdmagness