Leonardo and Michelangelo's Flops and Failures
- Gerriann Brower
- 2 hours ago
- 8 min read
Even great artists, Michelangelo and Leonardo da Vinci included, had flops and failures. Renaissance art was not a sequence of flawless masterpieces. There were countless unfinished, abandoned, and rejected artworks. Markets and patrons changed, or sometimes the design or materials were flawed. Not every commission became a Mona Lisa. Early Modern Italy was neither peaceful nor politically stable. Conflicts, changing rulers, and uncertainty were a way of life. Famine, death, and economic struggles were common. Risks were ever-present.
Art failures usually fell into two categories—either production problems or market risks. Production problems could be a flaw in a marble block, payment disputes, or political conflict. Market risks included rejection of the work, poorly executed work, or harsh criticism of the artwork.
Production Issues
Imagine two monumental paintings by two great rivals: one by Leonardo da Vinci across the room from one by Michelangelo. As an established master with a very different style from the young Michelangelo, the paintings would have been two masterpieces equal to the Last Supper and the Sistine Chapel. It never came to fruition due to Leonardo’s experimentation and the political ups and downs of the Medici family.
Florentines longed for a non-Medici dominated republic, one in which they would have representation and the ability to govern. The Medici longed for complete family control of the city and its territories. In the early 1500s the Medici had been booted out, just as Michelangelo had finished the David. The newly formed Florentine Republic engaged Leonardo and Michelangelo to paint battle scenes honoring the republic in the Great Council Hall. Their artwork would constitute a powerful force for the new Florentine Republic, with council members governing the city surrounded by these murals.
In his late twenties, Michelangelo embarked on creating a fresco for the hall. Tasked with representing Florentines prepping for the Battle of Cascina against Pisa, he spent many months setting up his workshop, procuring supplies, planning, and drawing full-scale cartoons for each scene. To give a sense of the size of the proposed fresco, Michelangelo’s cartoon measured about 1251 square feet and consisted of over four hundred sheets of paper. It took five days just to glue the sheets of paper together to make the cartoon.

Across the room from him was Leonardo da Vinci, also asked to paint a battle scene in the hall. He started about 1504; about the same time he began the Mona Lisa. Leonardo’s Battle of Anghiari celebrated the Florentine military victory against Milan. Leonardo had set up shop about six months before Michelangelo. He willingly opened his studio to artists and citizens, who flocked to see what the famous artist was up to.
This mural would be Leonardo’s second, and last, wall painting. The Last Supper was his first wall painting. The Battle of Anghiari was larger than the Last Supper. Leonardo ordered about fifty pounds of flour to make a water-based paste to glue the paper sections together. Assistants glued the sections together and reinforced the cartoon along the edges so it could be placed on the wall.
Leonardo was intent on experimenting with different techniques. He completed the Last Supper in1498, and after a few decades it showed signs of deterioration. He preferred working in oil rather than painting on wet plaster. Fresco did not suit his artistic personality as he favored retouching, editing, adding, and changing his paintings. Leonardo went against tradition when painting a mural. He used pigments artists never used with fresco and prepared the wall as if it was a wood panel. Large narrative scenes also did not hold appeal for the artist. With the exception of the Last Supper and the Battle of Anghiari, he never included more than four figures in a painting. His battle scene measured fifty-seven by twenty-three feet and probably would have included hundreds of figures.
Leonardo began his fresco for the Great Council Hall using an experimental technique of an oil-based primer on the wall instead of the traditional fresco preparation. His pigments would not adhere to the wall. If they did adhere, they wouldn’t dry. Summer was humid and hot. Leonardo wrote about his troubles. Cartoons ripped, thunderstorms interrupted his work, rain poured down, and his paint would not dry. In an effort to accelerate drying, he lit a fire. The paint melted and dripped down the wall. Leonardo wrote he began to paint at 1:00 pm on June 6, then “The cartoon ripped. The water spilled and the vessel containing it broke. And suddenly the weather became bad, and it rained so much that the waters were great. And the weather was dark as night.”*
Unfortunately for this commission, the Medici regained power long before the frescoes were completed, resumed control of the city, and dissolved the republic. The Medici had no interest in frescoes commissioned by the republic. We are not sure how much Leonardo painted before he either abandoned the commission or the Medici ended his work. Michelangelo stopped preparing for the commission and moved on to work for Pope Julius II. Their drawings and cartoons were sold or destroyed, and we only have partial copies. Their cartoons became sought-after collector’s items.

Engravers distributed copies widely. Marcantonio Raimondi captured Michelangelo’s signature treatment of musculature and movement of the body to express emotion. More than one hundred years later, Peter Paul Rubens was inspired by Leonardo’s rearing horses and men fighting for the standard. The cartoons became a learning opportunity and teaching tool for artists, a way to copy the masters while developing their own styles.
It is a shame the paintings never were completed as they would have served as exceptional examples of their work. Five years later Michelangelo went on to paint the Sistine Chapel ceiling. He worked as painter, architect, and sculptor for nearly six more decades. Leonardo later worked in Milan, for the King of France, traveled to Venice, and worked in Rome under Pope Leo X. His time in Rome coincided with that of Michelangelo and Raphael, although Michelangelo and Leonardo generally avoided each other socially and professionally. Leonardo spent his last three years in France under the patronage of King Francis I. He kept the Mona Lisa with him all along as a work in progress (along with two other paintings) until his death.
Michelangelo and Leonardo were expert draftsmen and closely studied the human body in preparation for their frescoes. Leonardo wanted to understand how the body moved and worked, and Michelangelo posed the body to convey emotion. Which red chalk drawing do you think is Michelangelo’s and which one is Leonardo’s? (Answer at the end of the post.)
Market Shift
Decades later, Michelangelo painted the Last Judgement in the Sistine Chapel. He labored on the painting for five years in his sixties. The hard work of climbing up and down scaffolding, painting, and managing a monumental wall painting took its toll mentally and physically. He sustained a fall from the scaffolding while painting, which delayed the completion. It was a labor of love for his faith and his patron, Pope Paul III.
His once close friend Sebastiano del Piombo prepared the wall, not for standard fresco, but primed it for oil paint. By the mid-1530s, oil painting on canvas was becoming the preferred medium. Michelangelo never painted oil on canvas and had no intentions of doing so. Oil painting a mural would be cutting edge and highly risky. Sebastiano’s involvement in the preparation for oils caused a falling-out with Michelangelo. He derided the medium of oil as appropriate for women and lazy people like Sebastiano. He removed the oil preparation and readied it for traditional fresco.
It had been many years since he had painted a large-scale fresco. The Last Judgement contains over four hundred figures on two thousand square feet. There are precedents depicting the end times as Christ judges humankind. Those on Christ’s left side (the sinister side or sinistra) are condemned to hell, and those on his right rise up, reconstituted from skeletons to human form, joining him and Mary in heaven. Judgement scenes are distinctly hierarchical; however, Michelangelo has created more fluid boundaries between the divine and the abyss. Hell is inhabited by monstrous beasts inflicting unspeakable consequences for sins. Heaven is peaceful and orderly.
Michelangelo limits his background to brilliant lapis lazuli. Humans structure the space, congregating on different levels up, down, and on horizontal bands. Space is condensed in the end times with little to no perspective or depth. Nudity is pervasive, as in God’s eyes we are all equal. Under Christ’s left leg, St. Bartholomew holds a knife, the symbol of his martyrdom, while grasping his skin painted with Michelangelo’s self-portrait.
Michelangelo, Last Judgment, 1536-41, Vatican Museums, Rome, Wikimedia Commons, public domain. Giovanni Ambrogio Figino, Nude Demon Encircled by a Serpent, After Michelangelo’s Last Judgement, 1548-1608, Metropolitan Museum of Art, New York, open access.
When the fresco was about two-thirds complete, Pope Paul III and the papal master of ceremonies, Biagio da Cesena, viewed the wall. Biagio was appalled at the nudity, especially for saints, claiming the art was more appropriate for a bathhouse or tavern. Michelangelo responded with his paintbrush and included Biagio’s portrait in hell. He is pictured as Minos, a tormented figure with ass's ears in the lower right-hand corner of the fresco. An enormous serpent encircles him and bites him in the genitals. Biagio complained to the pope, requesting the removal of his portrait. Pope Paul responded to Biagio’s request by telling him that as pope he had some influence in heaven, but no authority in hell.
The Last Judgement was unveiled in late 1541 and was not received with the same acclaim and awe that the Sistine ceiling had nearly thirty years earlier. Although hardly a failure, the cultural impact of the Sistine Chapel ceiling was far greater than that of the Last Judgment. Some said Christ was too young, and he should have been painted with a beard.
However, Biagio was on to something. Times had changed since the Sistine ceiling. Martin Luther’s teachings, the German troops attacking Rome in the Sack of Rome, the Reformation, and a more cautious attitude towards religious art prevailed. Criticism of the fresco persisted throughout Michelangelo’s life. Immodest portrayals of heavenly figures were viewed unfavorably. Some accused Michelangelo of losing his piety, or that he was past his prime. Michelangelo was not accustomed to criticism at this point in his storied career.
The human body was divine for Michelangelo, a metaphor for God’s creation. One year following Michelangelo’s death, his dear friend Daniele da Volterra carried out instructions to modify the nudity under the Council of Trent’s decrees. Daniele, an accomplished artist in his own right, lived with Michelangelo and was at his bedside when he died. He added loincloths and robes to mask the genitalia of various figures. It must have been a troubling task to paint over his friend’s masterpiece. Daniele became known as the “pants painter.”
*Bambach, 2003, 235.
The Standing Male Nude is by Leonardo da Vinci. The male nude with arms and left leg raised is Michelangelo’s study for the Sistine Chapel ceiling. He ran out of room to draw his feet and flipped the paper over to continue drawing. The figure is painted in the corner by the Prophet Daniel. Leonardo da Vinci, Standing Male Nude, 1504-6, Royal Collection Trust HM King Charles III, RCIN 512956. Leonardo made studies of male nudes in preparation for the Battle of Anghiari fresco. Michelangelo, Study for the Nude Youth over the Prophet Daniel (recto), 1510-11, The Cleveland Museum of Art, public domain.
Sources
Bambach, Carmen C. “The Purchases of Cartoon Paper for Leonardo’s ‘Battle of Anghiari’ and Michelangelo’s ‘Battle of Cascina.’” I Tatti Studies in the Italian Renaissance 8 (1999): 105–33.
Bambach, Carmen C. Leonardo da Vinci: Master Draftsman. Metropolitan Museum of Art, Yale University Press, 2003.
Bambach, Carmen C. Michelangelo: Divine Draftsman and Designer. Metropolitan Museum of Art, Yale University Press, 2017.
Nelson, Jonathan K. and Richard J. Zeckhauser. Risks in Renaissance Art: Production, Purchase, and Reception, Cambridge Elements: The Renaissance Cambridge University Press, 2023.
Wallace, William E. Michelangelo: The Artist, the Man, and His Times. Cambridge University Press, 2011.







