Criminals and Courtesans: Caravaggio’s 20 Most Famous Paintings
By the late 16th century, art in Central Italy had hit a plateau. Still in the shadow of Renaissance greats like Michelangelo and Raphael, painters strove to capture the ideal of beauty embodied in the muscular figures and bright classical backdrops of these earlier masters. Then arrived Caravaggio, who in the words of one near contemporary had “come into the world to destroy painting.” Caravaggio sought to introduce a more visceral form of art, one that was more relatable and dramatic. His saints (painted from a small number of models) are ordinary people, with dirty feet and ruddy complexions. They appear in moments of high drama, isolated by a heavy all-encompassing shadow. The emotional tension in Caravaggio’s art far surpassed anything created by other painters of the day. Though underappreciated at the time, the magnetic appeal of Caravaggio’s innovative style would influence generations of artists for centuries afterwards.
Below is a full introduction to the art of Caravaggio, beginning with an extended bio, a brief introduction to his style and legacy, then a run through of his most famous paintings. For those interested in a specific painting, click on the link in the table of contents below to be taken directly to the desired section.
Table of Contents
The Life of Caravaggio
Beginnings
In talking about Michelangelo Merisi da Caravaggio, it is first useful to unpack the name. Da Caravaggio simply means “from Caravaggio,” the village near Milan where the artist was born. Though we refer to him as Caravaggio today, his contemporaries called him by his given name, Michelangelo. As best I can tell, the moniker “Caravaggio” seems to have been applied only to avoid confusion with the earlier Renaissance master in whose shadow Caravaggio lived and worked throughout his life.
Born in 1571, Caravaggio grew up in a modestly well off family. His father, Fermo Merisi, was a stone mason with his own workshop in Milan. His mother, though not highborn herself, came from a family with strong links to several important noble families. These links had been established by her father (Caravaggio’s grandfather), who was a land surveyor for the powerful Sforza and Colonna families. Throughout Caravaggio’s life, the Colonna family would be among his most unwavering supporters, coming to his aid again and again.
These middle-class roots and strong connections to powerful noble families might have made for an ideal start for an aspiring artist like Caravaggio. Unfortunately, whatever peace and security Caravaggio’s family might have enjoyed early on came to an end with a plague outbreak that struck Northern Italy in 1576.
The family took precautions, leaving the more crowded Milan for its home in the town of Caravaggio. In the countryside, the Merisis managed to evade the early stages of the pandemic. Unfortunately, in 1577, their luck ran out. That year, both Caravaggio’s father and paternal grandfather became ill, succumbing on the same day.
Their deaths proved to be a disaster for the family. Both had died without a will, leaving the family to fight with distant relatives for their inheritance. While the family did receive some property, much was lost to uncles and other relations.
Learning to Paint
Whatever challenges they may have faced, Caravaggio’s mother seems to have made due with the modest inheritance. In 1584, at the age of 13, Caravaggio’s mother paid a hefty sum to have her son apprenticed to Milanese painter Simone Peterzano. Unfortunately, not much seems to have been achieved during this apprenticeship. A poor student, Caravaggio learned little beyond the rudiments of oil painting and – after four years – he moved on.
The next part of Caravaggio’s life is shrouded in mystery. Murmurs of whoring, murder, and a year in prison swirl around him during this time period, though nothing is known for sure. Whatever happened, by 1592 Caravaggio was in Rome, the city where his career would at last take root.
Caravaggio’s entry into Roman artistic circles was relatively smooth. After a couple false starts, he soon found a position in the workshop of Giuseppe Cesari, who though only three years older than Caravaggio was quickly becoming the most famous artist in the city. In Cesari’s workshop, Caravaggio began to seriously apply himself to painting. In his free time, he painted Sick Bacchus and Boy with a Basket of Fruit, both of which showed real promise.
As his talent grew, Caravaggio began to feel stifled in Cesari’s workshop. Try as he might, he remained relegated to painting “flowers and fruit” on the margins of larger works. This put him at the lowest rung of the painting hierarchy – well below those who painted animals, landscapes, and the most exalted of all, the human figure.
Eventually, Caravaggio set out on his own. He began to paint independently, selling his works through a local art dealer. It wasn’t long before two of these works (The Fortune Teller and Cardsharps) came to the attention of his first great patron, the powerful cardinal and art lover, Francesco Maria del Monte.
Cardinal Francesco Maria Del Monte: Caravaggio’s First Patron
Cardinal del Monte was a consummate church insider. In the world of Roman politics, it was he who protected the interests of the Medici (the powerful banking family which dominated Florentine politics) and their French allies. His most notable achievement in this regard was ensuring the acceptance of Henry IV’s conversion to Catholicism; an act which established Henry as the uncontested King of France and ensured the Catholic Church remained the wealthiest and most powerful religious institution in Europe.
When not engaged in geopolitics, del Monte was pursuing his other great passion – the patronage of painters and musicians. With his support, Caravaggio at last found the recognition he had long craved. Sometime in the early 1590’s, Caravaggio moved into del Monte’s home, Palazzo Madama. Here, he further refined his technique, painting The Musicians, St Francis of Assisi in Ecstasy, and Rest on the Flight into Egypt.
Caravaggio’s most famous works of this period, however, was likely his Medusa (discussed below), which del Monte gave as a wedding gift to his benefactor, Ferdinando de’Medici. This work of classical allegory – with its gruesome depiction of the mythological creature’s decapitation – was reportedly cherished by Ferdinando, who displayed it prominently within the Medici collections.
The Contarelli Chapel: Caravaggio’s Arrival
Though paintings on classically inspired subjects like Medusa were a staple of Caravaggio’s early career, it was religion which really interested him. He was especially keen for public commissions, which would see his works displayed for all to see in the great churches of Rome. Fortunately for Caravaggio, he had found the right patron.
Using his influence, del Monte secured a commission for Caravaggio to paint the long unadorned Contarelli Chapel in the Church of San Luigi dei Francesi. Ironically, Caravaggio’s former employer, Giuseppe Ceseri, had been originally contracted to undertake the work. He, however, never completed it, noting he had more pressing open commissions. At del Monte’s urging and with the Pope’s blessing, the commission was transferred to Caravaggio.
The chapel was to be dedicated to St Matthew (Contarelli’s name saint). Commissions of this scale would generally have called for a series of wall frescoes. Caravaggio, however, chose to paint in his preferred medium – oil and canvas – completing two lateral works (The Calling of St Matthew and The Martyrdom of St Matthew), and one altarpiece (The Inspiration of St Matthew).
Completed in 1600, these now stand among Caravaggio’s most highly regarded works. They are a powerful display of both raw artistic talent and the dramatic chiaroscuro (light-dark contrast) which would come to define his artistic style. In a city still redolent with memories of Michelangelo and Raphael, this was something never before seen.
Caravaggio’s Detractors
Following the completion of these paintings, Caravaggio’s star rose rapidly. In the years that followed, he would paint some of his most famous works. Pieces like The Taking of Christ, The Crucifixion of St Peter, and Amor Vincit Omnia, would introduce a whole new style of art; one which more fully explored the dramatic potential of painting than anything that had come before. These works, among the first of the Baroque period, would become touchstones for artists in the succeeding two centuries.
Then, beginning around 1603, the tide began to turn against Caravaggio. While many responded ecstatically to his unique style of painting, others were less enthused. Among Caravaggio’s fellow artists, some were critical of his realism, which they believed reflected a lack of artistic imagination. Within the clergy, some were disturbed by his depictions of barefoot saints and grizzly acts of martyrdom, which in their eyes lacked decorum.
As this view took hold, Caravaggio began to struggle to win new Church commissions and even had some of his pieces rejected. His paintings were still in high demand among prominent private collectors, but this appears to have been insufficient to assuage the artist’s fragile ego. As criticism of his work grew in intensity, he became increasingly erratic, displaying behavior that would repeatedly land him in trouble with the law.
Caravaggio Fights the Law (and the Law Wins)
Caravaggio’s many run-ins with the papal police in the years 1603-1606 are the stuff of legend. Crimes he was arrested for include attacking a man with a hatchet in a crowded public square; defacing the house of young woman who had rejected his advances; and throwing a plate of artichokes at a waiter over a perceived slight.
In each instance, he avoided serious punishment only through the intervention of powerful supporters, including Cardinal del Monte, the French Ambassador, and the Colonna family. But in 1606, Caravaggio finally committed a crime so serious that even his most ardent backers could not get him off.
That year, Caravaggio murdered Ranuccio Tomassoni, a local pimp who also happened to be a scion of one of Rome’s most powerful families. No one knows for sure why Caravaggio murdered Tomassoni. A number of possible reasons have been put forward, including a disagreement over a tennis match, settling of a gambling debt, or rivalry for the affections of one of Tomassoni’s prostitutes. Whatever the cause, Caravaggio was forced to flee Rome, never to return.
On the Lamb
Caravaggio first fled to the hills outside Rome, then on to Naples. Even when on the lamb, however, he continued to paint. Among his first works after fleeing Rome was his David and Goliath, a gift for the head of Vatican justice, Cardinal Scipione Borghese (who coincidentally was a big fan of Caravaggio’s art).
The piece (discussed below) depicts David presenting to the viewer his trophy, the severed head of Goliath, which in this case is a self-portrait of Caravaggio. The painting served as Caravaggio’s plea for clemency, offering a figurative head for a real one. Borghese would ultimately support Caravaggio’s efforts to obtain a pardon, but given the seriousness of his crime, it would take time.
Not long after painting David and Goliath, Caravaggio continued on to Naples, then under Spanish control and well beyond the reach of the Papal States. While in Naples, his painting became even darker. Perhaps his most notable work from this period is The Seven Acts of Mercy, a swirling and shadowy painting which became an altarpiece for the recently consecrated church of Pio Monte della Misericordia. The piece was rapturously received by all corners of Neapolitan society, a marked contrast to the ambivalent response his work had attracted in Rome.
Other works painted by Caravaggio while in Naples received similar widespread acclaim. These paintings had an especially deep impact on later Neapolitan and Spanish artists, who embraced Caravaggio’s tenebrism with gusto. Yet despite the admiration Caravaggio’s work received there, he was not content to linger. After only a few months, he set out for Malta, seeking to join the Order of the Knights of St John (better known as the Knights of Malta).
Painting Toward a Knighthood
Caravaggio’s desire to join the Knights of Malta at this point in his life may seem strange, especially in light of his growing fame in Naples (then the second largest city in Europe). It could be that he saw it as a path to returning to Rome, as successfully joining the order would have resulted in an automatic pardon for the murder of Tomassoni. The elevated social status that would accompany a knighthood likely also appealed to his ever-sensitive ego.
Whatever his reasons for wanting to join, there was one big problem – membership in the Knights of Malta was open to only those of noble birth. To get around this would take some effort. Through the Colonna family, Caravaggio gained introductions to a number of senior knights who commissioned paintings from him. Eventually, his work came to the attention of the Grand Master himself, who asked Caravaggio to paint his portrait. The resulting work so impressed the Grand Master that he personally sought and received special dispensation from the Pope to invest Caravaggio with a knighthood.
There was, however, the matter of the passagio – a customary payment made to the order upon joining. Caravaggio, being close to penniless, naturally could not afford it. It was thus decided that in lieu of a financial contribution, he would paint an altarpiece for Valetta’s new Cathedral.
The painting that resulted, the Beheading of St John, is among the most haunting works Caravaggio ever created. Notable for its sparseness, tenebrism, and unflinchingly realistic depiction of violence, it is a fitting subject for the cathedral of the Church’s leading military order. Among all of Caravaggio’s works, this is the only one he ever signed, his signature formed from the blood of the martyred saint. With this painting, Caravaggio at last earned his knighthood.
Flight from Malta
It was at this point – having attained new heights of fame and prosperity – that Caravaggio’s erratic nature reasserted itself. In 1608, Caravaggio and five other knights broke into a private home where they assaulted and seriously injured a senior knight. A subsequent investigation identified Caravaggio as one of the lead instigators and he, together with one other, was immediately arrested.
However, as had happened two years earlier, Caravaggio would again escape punishment. After only a month in prison, Caravaggio (with the aid of some unknown party) escaped, fleeing to Sicily. Caravaggio spent almost a year in Sicily, moving between Syracuse, Messina, and Palermo as he evaded pursuit by the Knights of Malta. As he moved between the cities, painting proved to be his salvation. Powerful local patrons paid handsomely for his work, shielding him from the long reach of Valetta.
Eventually, Caravaggio made his way back to Naples, arriving in the summer of 1609. It was here that Caravaggio’s pursuers at last caught up with him. On his way home from a brothel, Caravaggio was ambushed by a group of assailants. These men, who were likely associates of the knight Caravaggio had attacked in Malta, left deep gashes in Caravaggio’s face – both disfiguring him and taking a steep toll on his health.
Death of Caravaggio
Following the attack, Caravaggio spent a considerable period convalescing. The seriousness of his injuries is apparent in his paintings from the period, which show nowhere near the skill evident in works he had done just a few months earlier. All, however, was not lost. In July 1610, word came that he may soon be pardoned for his crimes in Rome. His earlier gift to Cardinal Borghese (and possibly the promise of further works) appear to have borne fruit. Borghese was on the verge of obtaining a Papal pardon for the artist.
Not yet fully recovered, Caravaggio packed up everything he owned and rushed to board a ship to Rome. Unfortunately, his trip appears to have been premature. As he disembarked from his ship to enter the domain of the Papal States, he was stopped by customs officers and barred from entry. The resulting commotion between the artist and the customs officer appears to have spooked the captain who had ferried him to the port. The captain promptly put back out to sea with Caravaggio’s baggage still on board.
Eager to recover his property (which reportedly included three paintings meant as gifts for Borghese), Caravaggio set off overland to the ship’s next port of call, Port Ercole. He made it, but the exhausting trip in the middle of summer took a steep toll on his health. Overcome by exhaustion, Caravaggio fell into a fever, succumbing not long after. He was 38.
Modern investigations of his remains suggest he died from an infection, likely caused by his earlier wounds and compounded by exhaustion from his rush to Port Ercole. His remains were also found to contain high levels of lead, which Caravaggio (and other artists) frequently employed in pigments. It has been suggested that lead poisoning may have accounted for at least part of the erratic behavior Caravaggio displayed throughout his life.
Legacy and Style
While Caravaggio had been a relatively successful artist during his lifetime, following his death, he fell into obscurity. Caravaggio biographer Andrew Graham-Dixon suggests this was in large part a result of the critical opinion of some of his Roman contemporaries. While acknowledging the emotional resonance of his work and raw skill as a painter, these critics nevertheless judged him to have fallen short of the standards established by earlier Renaissance masters.
Most egregious in their view was the perceived lack of decorum in Caravaggio’s art. His paintings, filled with images of poverty and pain, were not to the taste then in fashion in Rome. In 16th century Rome, it was believed that the role of art was to depict objects and figures in an idealized manner, carefully arranged to illustrate sacred themes. Caravaggio’s decision to paint barefoot saints in darkened rooms suggested a fatal lack of artistic imagination, these critics believed.
Also troubling to many painters was Caravaggio’s practice of jumping straight into painting without first making preparatory drawings. Drawing was viewed as a critical element of the artistic process in Central Italy. It was the means through which great artists such as Michelangelo and Leonardo Da Vinci planned out their work, whether it be for a painting, a sculpture, or a design for a church.
Planning out compositions in advanced with preparatory drawings was particularly important when working in quick drying media, such as fresco. Caravaggio, however, painted exclusively in oil, which dried much slower. This made composing in paint much easier and was in fact already the norm in Venice and other places. Nevertheless, this practice didn’t sit well with Caravaggio’s Roman contemporaries, who like Michelangelo and Leonardo, placed a strong premium on drawing.
Further diminishing Caravaggio’s reputation was the persistent rumor that he was illiterate. Given where he grew up and his family background, it is highly unlikely that this is true. Moreover, inventories of his possessions showed that he owned a number of books, suggesting he was a well-read individual.
These criticisms, though subjective and occasionally misinformed, nevertheless enabled generations of scholars to discount the importance of Caravaggio’s art. Given that Caravaggio’s behavior during his lifetime did not make him many friend, few rallied to his defense, allowing this critical judgement to take hold. It would take until the mid-20th century before Caravaggio’s art would be given a second look.
Caravaggisti
While academic interest in Caravaggio’s art remained limited for centuries after his death, his work nevertheless inspired a whole generation of up and coming artists, sometimes referred to as the Caraviaggisti. These artists (which included Rembrandt, Velázquez, and Bernini) conscientiously adopted many of the same techniques used by Caravaggio in his paintings, creating what we know today as the Baroque period in art.
The most obvious element which attracted these artists was Caravaggio’s dramatic use of light and shadow, or chiaroscuro. The pervasive shadow in works like The Conversion on the Way to Damascus, The Calling of St Matthew, and David and Goliath, create a theatrical effect, heightening the tension inherent in the moment.
There are few precedents for the extreme tenebrism of Caravaggio’s art. Painters travelling through Rome as part of their training or merely looking for inspiration were struck by the dramatic quality of Caravaggio’s light and shadow, which would prove a lasting inspiration for artists throughout the Baroque. One need only look at Velazquez’s Las Meninas or Rembrandt’s The Night Watch to see the effect this had on European art.
Naturalism
Another element which attracted other artists to Caravaggio is the naturalism (or realism) of his art. While this was a key characteristic distinguishing Renaissance painting from its Gothic predecessor, by Caravaggio’s day, Roman artists no longer found nature by itself sufficient.
This is particularly evident in late-16th century depictions of the human figure. Art from this period is filled with extravagantly muscular figures (often drawn from the sculptures of Michelangelo) and plump women with elongated necks. Caravaggio instinctively moved away from this tradition, instead preferring to paint directly from live models. His bare foot saints with their ruddy complexions and rough hands are a far cry from the idealized figures painted by his contemporaries.
Caravaggio also extended this treatment to the world occupied by his figures. Rather than depict his subjects performing startling miracles in bright and colorful worlds, Caravaggio painted them in more modest settings – a shadowy barn, a squalid street corner, a humble tavern. This made his art more relatable, lending it an emotional resonance that often exceeded the more traditional Renaissance iconography.
Famous Paintings of Caravaggio
Below is a deeper dive into 20 of Caravaggio’s most famous paintings. As with any artist active in this time period, the fame of any individual painting is in part a function of where it is displayed. Nevertheless, I have done my best to include below what I believe are Caravaggio’s most important works, even if one may have to travel a bit off the beaten path to see it.
Early Works
Caravaggio’s earliest known works come from the period shortly after his arrival in Rome in the early 1590’s. Though many pieces from this period were lost, much still remains. In them, Caravaggio’s raw artistic talent is already apparent, especially in his extraordinarily detailed still life. Also notable about Caravaggio’s art from this period is his focus on classical allegory and other secular subjects – a sharp contrast with his later art which was almost exclusively religious. This likely reflects the tastes of his patrons, which at this point in his life did not include the Church.
1) Young Sick Bacchus
Caravaggio’s earliest attributable works come from his time as an assistant in the workshop of Giuseppe Cesari. Among the most notable is Young Sick Bacchus, which was painted around 1593.
This painting – a self-portrait of Caravaggio – is a peculiar piece. The strange yellow pallor of Bacchus’s skin, the huddled pose, and the manner in which he seems to covet the grapes in his hands suggests something subtly untoward. Add to this the neuroticism inherent in depicting himself in this manner and it’s not hard to see in it seeds of Caravaggio’s later erraticism.
Yet the work does also demonstrate Caravaggio’s skill as a painter. The dusty grapes in Bacchus’s hands, the skillfully folded classical tunic, and the strange twisting pose evinces a skill beyond that of an ordinary novice. Even more impressive though is the strange magnetism of the work. Bacchus, the god of wine and festivity, was also the God of madness. To depict him in this way suggests a deep and tantalizing darkness within.
2) The Cardsharps
Painted around 1594, this painting (together with The Gypsy Fortune Teller) brought Caravaggio to the attention of his first great patron, Cardinal Francesco Maria del Monte. It depicts a young nobleman being cheated at a game of cards in a tawdry gambling den.
The painting is a morality play, warning the viewer of the danger that awaits them in such games of chance. The young gentleman, enticed into the trap, is relieved of his pocket money by the waiting vipers – the logical consequence of his moral lapse.
Aside from the entertaining subject, the work is most notable for its depiction of an otherwise everyday scene. Neither a classical allegory or a religious painting, it depicts three ordinary individuals caught in a comical but relatively mundane moment. Such works are rare for the period. In the late 16th century Italy, almost all art depicted heroic deeds from classical mythology or a scene from the Bible or the life of a saint. Rarely did paintings include such lowlife cutthroats, and rarer still did they receive such sympathetic treatment.
It was a sign of what was to come in the art of Caravaggio. Ordinary people would figure prominently in many of his works. Sure they might be depicted in the guise of a saint or martyr, but looking past the subject of the painting, the individuals depicted were just the ordinary cast of characters one might encounter every day in the mean streets of 16thcentury Rome.
3) The Musicians
Painted in 1597 after joining the household of Cardinal Francesco Maria del Monte (the artist’s first great patron), this is the most complex work Caravaggio had yet attempted.
As many have noted, there is a certain awkwardness in the painting. The musicians are compressed into a tight plane within the piece – so close that the knee of the singer seems almost to project through the groin of the lute player. Some suggest this was the result of Caravaggio’s use of the same model for multiple figures. It also, perhaps, validates contemporary criticism of his practice of painting without first making preparatory drawings
This awkwardness aside, the painting still works as a musical allegory. Most interesting is Caravaggio’s decision to paint the group during a rehearsal. Musicians were often the subject of paintings, but usually they were depicted in concert or another idyllic setting. Caravaggio’s painting is a break with this tradition, which instead focuses on the artistic toil that goes into the creation and production of music.
Elevating this rehearsal is the classical clothing worn by the musicians and the presence of Cupid on the far left. The presence of these two elements suggests the virtue inherent in the musician’s toil. Adding to this is the self-portrait of Caravaggio, which faces out at the viewer from the back. This makes explicit Caravaggio’s identification with the toil of the musicians who are similarly engaged in the labor of artistic creation.
For more on this work, see: The Musicians by Caravaggio: The Joyful Toil of Artistic Creation
4) St Frances of Assissi in Ecstasy
One of Caravaggio’s earliest religious paintings, in this work we see the beginnings of much of what would become the artist’s dominant style in later years.
The work shows St Francis of Assisi – possibly the most venerated saint in Italy at the time – undergoing the stigmata (the suffering of wounds experienced by Christ during the Crucifixion). The Saint’s calm expression as he rests in the angel’s embrace convey a deep sense of serenity, perhaps obtained through this final surrendering to the will of God. Strangely, Caravaggio chooses only to depict the wound in St Francis’s side, not his hands or feet as was more common. This could suggest that the stigmata has only just begun.
As in so many of Caravaggio’s religious paintings, the work is enhanced by a high light-dark contrast (chiaroscuro). St Francis and an accompanying angel are bathed in a divine light while the world around them fades into darkness. This adds drama to the work in the same way a spotlight at a theater might accentuate a soliloquy.
The deep tenebrism of this work, its emphasis on the internal nature of spiritual experience, and the sparseness of the composition (with its almost exclusive focus on the two figures) would be recurring themes throughout much of Caravaggio’s religious art.
5) Medusa
Completed around 1598, this is one of Caravaggio’s more interesting works. The piece is made from a canvas stretched over a wooden tournament shield. According to mythology, Medusa could turn to stone anyone who gazed into her eyes. She was slain by the hero Perseus, who used the reflection from his shield to defeat her. Caravaggio’s work depicts the reflection in Perseus’s shield in the exact moment he decapitates the monster.
The image of Medusa is actually a self-portrait of Caravaggio. He is said to have used a convex mirror to get the proportions just right. The terrified expression frozen onto the severed head, with its bright streaks of blood shooting outward, were especially shocking to early viewers not quite used to such graphic depictions of violence. Interestingly, this would not be the last time Caravaggio would paint his own severed head – he would do so again 10 years later in his David and Goliath, discussed below.
Following its completion, the work went to Caravaggio’s patron at the time, Cardinal Francesco Maria del Monte. Del Monte in turn gave it as a wedding gift to his benefactor, Ferdinando de’Medici, the Grand Duke of Tuscany. The Grand Duke reportedly loved the ingenuity of the work, displaying it prominently within the Medici collections.
6) Judith Beheading Holofernes
This painting tells the story of the biblical heroine Judith, who sneaks into the tent of an enemy general (Holofernes) and slays him as he lies passed out in a drunken stupor. The painting is known today for its strong sexual overtones and vivid depiction of violence.
Viewing this work, we can almost hear Holofernes’s blood curdling scream as his head is visibly separated from his body. Judith looks down at the screaming and naked general, her expression a mix of disgust and concentration on the task at hand. Beside her, a maidservant holds a bag ready to receive the head.
Contemplating this painting, one can’t help but feel that Caravaggio is in his element. Violence, betrayal, a sexual tryst gone horribly wrong – these were all things Caravaggio had experience with and was able to channel into his art. Annibale Carracci (possibly the most famous Roman painter from this time period aside from Caravaggio) is said to have remarked about the work, “I don’t know what to say except that it is too natural.”
7) St Catherine of Alexandria
Completed around 1599, this haunting work depicts the 4th century saint and martyr, Catherine of Alexandria, daughter of the Roman governor of Alexandria.
According to legend, the Roman Emperor Maxentius ordered Catherine be tortured on a spiked wheel and executed for refusing to renounce her faith. Imprisoned, she daily received divine sustenance brought to her by a dove. When her jailers attempted to torture her, the spiked wheel shattered at her touch. All the while she continued to convert all those who visited her, including the Emperor’s wife, Valeria. At last, when she was ready, she allowed her jailers to go forward with her execution – a beheading by sword.
In Caravaggio’s painting, Catherine leans casually against the broken wheel, a portion of her dress spilling over the axel. Her pose is relaxed even as she caresses the sword that will bring about her death. She stares sidelong at the viewer, as if confident of God’s mercy. The scene is sparse; the brutality to come not yet realized.
The heroine in this painting is modeled by Fillide Melandroni – the same courtesan who modelled for Judith in Judith Beheading Holofernes. Unlike the earlier painting of Judith, violence here is only alluded to, leaving the viewer’s imagination to fill in the gaps.
Mid-Career
Most of Caravaggio’s best known works come from the middle years of his career, which run from about 1600 to 1606. It was during this period that Caravaggio’s unique style, with its sharp chiaroscuro and naturalism, reached its fullest potential. These works would form the foundation of Caravaggio’s legacy, inspiring generations of artist from all across Europe.
8) The Calling of St Matthew
As noted above, this was one of the trio of paintings Caravaggio made for the Contarelli Chapel, his first major Church commission.
In this painting, Matthew, the tax collector, sits at the table with his companions. The room they inhabit is dingy and spare, perhaps a basement. Jesus raises his hand toward Matthew, uttering “follow me.” Matthew appears confused by this command, pointing to his chest as if to ask, “who me”? He nevertheless rises in compliance, compelled forward by the peculiar magnetism of the stranger.
In this painting, we feel the full force of Caravaggio’s tenebrism. The shadow adds mystery to the partially concealed image of Christ while accentuating the dreariness of Matthew’s office. At the same time, the light emanating from outside appears almost divine. Matthew seems to be literally in God’s spotlight.
The painting tells a masterful story of redemption. Matthew, a tax collector and Roman collaborator, is in some ways the antithesis of everything Christ stands for. Yet despite his shortcomings, he is called by Christ into the light, ultimately becoming part of his inner circle and a celebrated evangelist. It suggests that anyone, no matter how lost, can be redeemed at any moment.
9) The Martyrdom of St Matthew
Painted not long after The Calling of St Matthew, The Martyrdom of St Matthew brings the story to its conclusion.
The painting shows an assassin standing over Matthew, blade at the ready. As he does so, the onlookers scramble aside, fleeing the armed youth. Overhead, an angel appears, passing to Matthew the martyr’s palm.
This painting is an electric work. One which together with The Calling of St Matthew secured Caravaggio’s reputation as one of the leading painters of Rome. The raw talent apparent in the painting, from the expert foreshortening in the figure of the assassin to the instinctive recoil of the onlookers, mark Caravaggio as among the most exceptional artists of any age.
Adding to the tension is the sharp chiaroscuro. An external light illuminates the assassin at the center of the painting. His tensed muscles ripple with energy. Like an explosion, he sets everyone else into flight. Even the light dims as the eye moves closer to the edges of the painting.
Amidst the tumult is a self-portrait of Caravaggio. The most distant figure in the painting, he looks back at the soon to be martyred saint – his expression a mixture of sorrow and helplessness.
10) The Conversion of St Paul on the Road to Damascus
Painted between 1600 and 1601, this was one of two pieces Caravaggio made to decorate the Cerasi Chapel in the Basilica of Santa Maria del Popolo (the other was The Crucifixion of St Peter). Santa Maria del Popolo sits just inside Rome’s northern gate and was thus one of first stops of many pilgrims to the city. It was an important commission for Caravaggio and one in which he initially floundered.
In his first attempt, Caravaggio had modeled his work after Michelangelo’s fresco on the same subject in the Vatican’s Pauline Chapel. Though the two artists shared a name, they otherwise had little in common. Unsurprisingly, the vision of Michelangelo failed to inspire when painted by Caravaggio’s hand.
His patrons rejected the piece but gave Caravaggio an opportunity to try again. On his second attempt, Caravaggio went back to his strengths, moving away from Michelangelo’s thundering fresco to one more focused on the internal spiritual experience, just as he had done in the earlier St Francis of Assisi in Ecstasy described above.
Unlike this earlier work, however, we do not see St Paul’s internal vision but rather its outward appearance. Paul lies flat on his back, arms outstretched in response to some invisible force. The horse looks on, perhaps startled by Paul’s flamboyant gesture, while a servant leads the animal around his stricken master. If not for the image of Peter’s crucifixion hanging directly opposite, the work would appear almost comical.
To the pilgrims who saw this piece, it would have been a reminder that not all miracles are heralded by choirs of angels. Rather, some miracles may only reveal themselves in the act of a man falling off his horse.
11) The Taking of Christ
Painted for the private collection of Cardinal Ciriaco Mattei, the work depicts the moment just after Judas’ kiss, the sign by which he was to identify Christ to the waiting soldiers. In this moment, we witness the beginning of the Passion, a series of brutal events culminating in Christ’s crucifixion. For now, however, it is just a small tussle in the night.
Caravaggio has cropped the scene to its bare essentials. Jesus recoils from Judas, who stares into Christ’s eyes as if looking for a reaction to his betrayal. As he does so, the soldiers collapse in on Jesus, a dark steel gauntlet reaching for his collar. Christ looks down at the approaching hand, a look of weariness in his eyes.
The chiaroscuro in the painting is remarkable. The gleam of the cold metal armor of the soldiers foreshadows the brutality to come, while the dark, all-encompassing night, forecloses any possibility of escape. Salvation may await, but it will be a long and difficult road to reach it.
12) Sacrifice of Isaac
Painted in 1603, Caravaggio completed this work at the height of his career. Commissioned by Cardinal Maffeo Barberini (the future Pope Urban VIII), the painting is a classic example of Caravaggio’s ability to capture the most critical moment of a story. As told in Genesis, God commands Abraham to sacrifice Isaac, his favorite son, as a sign of his faith. However, just as he is about to do so, an angel stops him, offering a ram to be sacrificed in Isaac’s stead.
The threatened violence in this painting is palpable. You can feel it in the cold practiced grip with which Abraham pins Isaac’s neck against the stone and in the cold gleam of the butcher’s knife he holds near Isaac’s neck.
This drama is further amplified by the sharp chiaroscuro. A shaft of light originating over the angel’s shoulder cuts diagonally across the work, ending on the ram which is to take Isaac’s place.
This painting would have a deep influence on later Baroque artists, most notably Artemisia Gentileschi and Rembrandt, who would paint their own similarly menacing takes on the story.
For more on this painting, see: The Sacrifice of Isaac and the Screaming Realism of Caravaggio
13) The Entombment
Of all Caravaggio’s paintings, The Entombment was the most widely acclaimed during his lifetime, with even his harshest critics expressing begrudging admiration. The painting is closely modelled on Michelangelo’s Pietà. Like that work, Christ’s lifeless body is unflinchingly depicted, sagging under the support of his followers. Most notable is Christ’s right hand, a mirror image of the carefully crafted veins and musculature in Michelangelo’s sculpture.
But whereas Michelangelo depicted Christ in the lap of a youthful virgin Mary, Caravaggio did not. His aged Mary stands by Christ’s side, staring stoically down at the body of her lifeless son. Beside her is Mary Magdalen, drying her tears, while behind is Mary of Cleophas, who somewhat theatrically reaches toward heaven.
Holding Christ is John the Baptist (identifiable by his characteristic red cloak) and Nicodemus, whose face some speculate to be a portrait of Michelangelo. The physical exertion is evident in their tensed posture as they lower Christ into the tomb.
Against the dark backdrop, the painting belies none of the miracles evident in other depictions of Christ’s entombment. No choirs of angels descend in celebration or images of fruit foreshadowing the resurrection to come. In this moment, there is just an ordinary family laying to rest a man taken from them much too soon.
14) The Death of the Virgin
A brutal work, the painting was meant to be an altarpiece for the church of Santa Maria della Scala in Rome. It depicts the corpse of the recently deceased Virgin Mary. Unlike The Entombment, Mary is again young. Her skin, however, has taken a yellowish pallor and her stomach is somewhat bloated. The only obvious symbol of the divine is the thin halo over her slumping head.
The apostles stand around her in mourning. They stare on with mixed expressions, some contemplative while others are filled with grief and despair. Beside the Virgin Mary is seated Mary Magdalen, slumped over with grief. From this point on, she is alone in the world.
Somewhat discordantly, a bright red canopy hangs overhead. The same color of the Virgin’s dress, the folded canopy mirrors the body of Mary below, perhaps suggesting the departure of Mary’s soul from its earthly body to a new realm above.
It is a deeply moving work but went unappreciated by Laerzio Cherubini, the man who had commissioned the piece. A lawyer by profession, Cherubini charged that the figure of Mary had been modeled by a prostitute and thus lacked decorum. The painting was ultimately replaced by a more traditional Assumption of the Virgin painted by Carlo Saraceni. Saraceni’s work shows Mary surrounded by angels preparing to be transported to Heaven. Formulaic and crudely handled, Saraceni’s painting possesses nowhere near the emotional depth of Caravaggio’s original.
Interestingly for art history, the painting was purchased from Cherubini by future Caravaggio biographer Giulio Mancini. Mancini then sold it on to the Duke of Mantua clearing a tidy profit from the transaction. The Duke had purchased the painting on the advice of his agent, the great Flemish painter Peter Paul Rubens. Rubens, who was deeply influenced by the art of Caravaggio, would become one of the best-known painters in the history of Western art.
But before Rubens sent it on to Mantua, he and another of the Duke’s agents were approached by the city’s painting guild. The guild requested the work be put on public display before it left the city, as hardly anyone had seen it. Rubens and the other agent agreed, allowing it to be displayed for an entire week. During this period, the painting received widespread acclaim – a far cry from the rude reception it had received from the man who had initially commissioned it.
Later Career
The final years of Caravaggio’s life saw the artist almost constantly on the move, fleeing the many enemies he had made through his violent and erratic behavior. Despite the instability in his life (or perhaps because of it), his art entered an entirely new plane of expressiveness. These paintings lose some of the theatricality of earlier works, making them more relatable and further deepening their emotional impact. Collectively, they mark Caravaggio as the equal of any great master who came before or has since.
15) David and Goliath
Painted in 1606, this work is one of the darkest Caravaggio ever created. The painting shows David presenting to the viewer his trophy, the severed head of Goliath (a self-portrait of Caravaggio). David looks at the head with an expression of discomfort, perhaps even compassion for the slain monster, whose head appears contorted in agony. A heavy shadow encompasses both David and the head, isolating them in an encroaching oblivion. It is a gloomy way to paint a scene usually regarded as David’s moment of triumph.
To understand this work requires further context. This painting was a gift for Cardinal Scipione Borghese, the head of Vatican justice. Caravaggio had just murdered a man in cold blood, forcing him to flee Rome and go into hiding. The painting is a plea for mercy from Caravaggio. He is offering to Borghese a figurative head hoping he will accept it in place of a real one.
As noted above, Borghese was a fan of Caravaggio’s work, so the ploy wasn’t quite as crazy as it might appear on the surface. It even appears to have worked. There is evidence that Borghese was on the verge of winning Caravaggio a pardon just a few years later. Unfortunately, Caravaggio died shortly before he was able to receive it.
For more on this work, see: David and Goliath by Caravaggio: The Art of Despair
16) Seven Acts of Mercy
Caravaggio painted this work in 1606 for the recently consecrated Chiesa del Pio Monte della Misericordia (Church of the Pious Mount of Mercy) in Naples.
Set at the intersection of two narrow Neapolitan alleys, the piece perfectly captures the charitable spirit upon which the church was built. All around this crowded urban scene are individuals offering aid to the needy: a nobleman cuts off a piece of his tunic to give to a beggar; a pilgrim is given shelter by an innkeeper; and a woman breastfeeds a hungry prisoner. The piece conveys the urgent need for charity at that moment in Naples while highlighting the religious imperative of offering it.
From a stylistic perspective, it also shows Caravaggio’s shadowy chiaroscuro at its most elegant. The pale skin of the foreground beggar, the breast of the woman feeding the man in jail, and the bright swirling angels up top stand out sharply against the shadowy night-time world they inhabit. Their striking forms have the beauty of white veins running through black marble. It is one of the most visually appealing pieces to come out of the entire Baroque period.
17) Beheading of St John the Baptist
Like David and Goliath, this work also holds an interesting place in the life of Caravaggio. Painted as an altarpiece for the new Cathedral of St John in Valetta, it remains in situ in the church’s oratory. Completed in 1608, the work served as Caravaggio’s passagio – a customary payment made by one seeking to join the Knights of Malta. This is the only painting Caravaggio ever signed, using the blood spilling from St John’s neck to spell out Fra Michelangelo – the Fra hear meaning brother, a reference to Caravaggio’s new status as a knight.
Though Caravaggio’s time with the Knights of Malta would end in disgrace, this work nevertheless remains among his most famous. In it, Caravaggio again offers a hyper-realistic image of violence. St John, his throat slit, lies forcefully pinned against the ground. The manner in which he is murdered resembles the method by which a lamb might be slaughtered.
Accentuating the violence is a high light-dark contrast. Though the scene occurs at night, the figures are bathed by a sharp overhead light. This contrasts with the gloom of the courtyard and the impenetrable shadow of the doorway and window.
These ordinary surroundings remind the viewer that even a great saint may be martyred alone in a dark courtyard, an especially pertinent message for those seeking to join the ranks of the Knights of Malta.
18) The Burial of St Lucy
Caravaggio painted this work while on the run from the Knights of Malta. A fugitive from justice, the artist sought refuge in Syracuse. The Syracusan Senate was amenable to protecting the artist but at the price of a painting.
The painting they requested was an altarpiece for the recently renovated Basilica of Santa Lucia al Sepolcro. Caravaggio agreed, beginning work in late 1608. It would take him only around a month to complete the work, a very rapid pace for such a monumental painting.
The painting depicts the martyred St Lucy being laid to rest in the old Christian catacombs of Syracuse. St Lucy had suffered a particularly brutal martyrdom. Denounced by her would-be-husband to the authorities, she was ordered removed to a brothel. However, when the time came to take her away, no one was able to move her. A fire was lit around her and burning oil poured on top of her but still she remained “as impassive as a mountain.” As a last-ditch effort, a sword was stabbed through her neck. Though it pierced her, she did not die. Lucy asked for one last communion and when it was given, she at last perished.
Caravaggio’s painting, much damaged by time, depicts the aftermath of these events. Two massive laborers shovel away in the foreground. Behind them lies the lifeless body of St Lucy, languid and pale. Around her is a crowd of mourners. Among them standing prominently in the center is a young man with a bright red scarf, an attribute of John the Baptist.
A young woman, put to death by the violence of men, is prepared for burial in these massive anonymous catacombs. Yet in the darkness, the Lord’s emissary stands beside her. This was Caravaggio’s gift to the people of Syracuse.
19) The Raising of Lazarus
Painted in 1609 as an altarpiece for the chapel of the de’Lazzari family, the piece depicts one of Christ’s most well-known miracles – the resurrection of Lazarus of Bethany.
According to the gospels, Lazarus’s sisters requested Christ go with them to Bethany to heal their sick brother. Christ, however, delayed and by the time he arrived, Lazarus was dead.
Lazarus’s sisters lamented that Christ had arrived too late, not believing he had the power to revive the dead.
Christ, however, proceeded to the tomb. When the stone cover of Lazarus’s tomb was opened, Christ commanded “Lazarus, come forth.”
This is the moment depicted in Caravaggio’s dark painting. Christ reaches out toward Lazarus with a gesture reminiscent of Michelangelo’s Creation of Adam. A crowd looks on, eager to see if Christ does indeed hold the power to restore the dead to life.
The corpse of Lazarus, pale and wasting is caressed by one of his sisters. No sign of life is visible in his eyes. His arms, however, are held up and one of his hands lifts as if to touch the light. The crowd does not yet realize what is happening, but the miracle is already half accomplished. In the next moment, Lazarus will indeed come forth.
Surrounding the small crowd is a pervasive darkness, with a bright light emanating from somewhere behind Christ. The piercing light is again a metaphor for the theme of the painting. As shadow gives way to light, death too gives way to life.
20) Adoration of the Shepherds
Caravaggio’s Adoration of the Shepherds is perhaps the best known of his Sicilian works. Painted in 1609, one year before his death, the painting gives full expression to the unique style Caravaggio cultivated over the course of his career.
The piece is a departure from earlier Renaissance depictions of the Nativity, which show bright scenes filled with angels and well-healed worshippers. Caravaggio takes a more naturalistic approach, returning to themes of humility and holy poverty emphasized in biblical accounts.
The result is a moving work of a tired mother with her newborn child. She is attended by Joseph and the shepherds, whose bare feet and ruddy complexions meld well with the humble surroundings. This further connects the themes of material poverty and spirituality – a reflection perhaps of the beliefs of the Franciscan friars for whom this piece was painted.
The skill with which Caravaggio conveys the emotive ecstasy of this moment is extraordinary. The addition of angels or exotic animals or majestic scenery (staples of Renaissance Nativities) would in no way add to the miraculous feeling of this work. It’s a powerful demonstration of the emotional resonance of the humble piety at the heart of Caravaggio’s art.
For more on this work, see: Adoration of the Shepherds by Caravaggio: A Light in the Dark
Sources/Further Reading on the Famous Paintings of Caravaggio
- Graham-Dixon, Andrew. “Caravaggio: A Life Sacred and Profane.” Allen Lane and Penguin Books. London. 2010 – A beautiful and very readable biography of Caravaggio. I highly recommend it.
- Swarzenski, Hanns. “Caravaggio and Still Life Painting: Notes on a Recent Acquisition.” Bulletin of the Museum of Fine Arts, vol. 52, no. 288, 1954, pp. 22–38.
- Christiansen, Keith. Caravaggio and “L’esempio davanti del naturale.” The Art Bulletin Vol. 68, No. 3 (Sep., 1986), pp. 421-445
- Chorpenning, Joseph F. “Another Look at Caravaggio and Religion.” Artibus et Historiae, vol. 8, no. 16, IRSA s.c., 1987, pp. 149–58