The car­i­ca­ture was once a high­ly-regard­ed art form, before it was cor­nered on the upper end by the New York Review of Books and on the more pedes­tri­an side by board­walk and street fair artists. Dur­ing the Euro­pean Renais­sance and the ensu­ing cen­turies of artis­tic devel­op­ment, near­ly every artist had a car­i­ca­ture side project—if only in the mar­gins of their sketchbooks—and some, like Leonar­do da Vin­ci, were wide­ly known and appre­ci­at­ed for their skill in the art.

Gen­er­al­ly renowned these days for the high seri­ous­ness of his Mona Lisa, Last Sup­per, and Vit­ru­vian Man, Leonar­do does not tend to be asso­ci­at­ed with grotesque humor. Yet the car­i­ca­tures “were some of his most pop­u­lar and influ­en­tial works,” writes Jonathan Jones at The Guardian, “from the 16th cen­tu­ry up to the time of [William] Hog­a­rth,” the huge­ly pop­u­lar 18th cen­tu­ry Eng­lish visu­al satirist.

These car­i­ca­tures con­nect Leonar­do not only to graph­ic art of the future but to an ear­li­er, Medieval world—the “hell­ish visions of Bosch and Bruegel.” They are “Gar­goyles,” wrote crit­ic Ken­neth Clark, “the com­ple­ment to saints; Leonar­do’s car­i­ca­tures were com­ple­men­tary to his untir­ing search for ide­al beau­ty.

And gar­goyles were the expres­sion of all the pas­sions, the ani­mal forces, the Cal­iban grunt­ings and groan­ings which are left in human nature when the divine has been poured away.” Clark tem­pers this char­ac­ter­i­za­tion by not­ing that these draw­ings “in their expres­sion of pas­sion­ate ener­gy, merge imper­cep­ti­bly into the hero­ic.”

Indeed, Leonar­do loved unusu­al faces and heads—he found odd-look­ing peo­ple of all kinds fas­ci­nat­ing, and turned them into tragi­com­ic fig­ures fit for the stage. Gior­gio Vasari, the 16th cen­tu­ry biog­ra­ph­er of Renais­sance artists, wrote that Leonar­do was “so delight­ed when he saw curi­ous heads, whether beard­ed or hairy, that he would fol­low any­one who had thus attract­ed his atten­tion for a whole day, acquir­ing such a clear idea of him that when he went home he would draw the head as well as if the man had been present.”

We can’t say that stalk­ing exhibits much respect for the kinds of bound­aries most peo­ple would pre­fer to main­tain, but Leonar­do’s behav­ior does dis­play a rev­er­ence for inter­est­ing human phys­iog­no­my, both a source and a foil for his ide­al­iza­tions of the human form. Leonardo’s car­i­ca­tures res­onate into the late 20th cen­tu­ry in the work of Ralph Stead­man, the gonzo illus­tra­tor and polit­i­cal car­toon­ist.

In his satir­i­cal illus­trat­ed biog­ra­phy of Leonar­do, Stead­man remarked that the Renais­sance artist who enno­bled the human form also found “that man was not what he appeared to be, despite the pre­vail­ing atmos­phere of fine thoughts and high aspi­ra­tions.” Stead­man quotes a pas­sage from Leonardo’s note­books that sounds much more Swift­ian or Rabelaisian than high-mind­ed Renais­sance human­ist:

His Holi­ness the Pope sur­round­ed him­self with none but craven guz­zlers, gross pre­tenders and a host of fawn­ing dig­ni­taries who gri­maced through their days at court with no more grace than beg­gars I had enter­tained in days gone by — though they had nei­ther choice nor wit to rise above them­selves and in that they had a rea­son.

Oh that I had ways to sure­ly serve their putrid mas­quer­ades and twit­tery to make a drag­on from the very menagerie with­in the Vat­i­can itself.

If I could take for its head that of a mas­tiff or set­ter, for its eyes those of a cat, for its ears those of a grey­hound, with the eye­brows of a lion, the tem­ples of an old cock and the neck of a water tor­toise. 

O vile mon­ster! How much bet­ter it for men that thou shouldst go back to hell! For this the vast forests shall be stripped of their trees; for this an infi­nite num­ber of crea­tures shall lose their lives.

Though the car­i­ca­tures may not go as far as the hor­ri­fy­ing hodge­podge in this descrip­tion, they do por­tray human beings with rather less clas­si­cal equa­nim­i­ty than the serene Mona Lisa or the very com­posed Christ. But due to Leonar­do’s skill and seem­ing­ly irre­press­ible love for the human form—even if he had a jaun­diced view of human nature—the car­i­ca­tures con­tin­ue to be inspir­ing pieces of work.

Relat­ed Con­tent:

Leonar­do da Vinci’s Vision­ary Note­books Now Online: Browse 570 Dig­i­tized Pages

Ralph Steadman’s Wild­ly Illus­trat­ed Biog­ra­phy of Leonar­do da Vin­ci (1983)

What Leonar­do da Vin­ci Real­ly Looked Like

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