Want to know more about Baroque art and Italian painter Caravaggio? We are Caravaggio experts, so you’ll learn helpful information about him and his works of art. Here are the most famous paintings you should not miss when trying to understand Caravaggio!
The 11 Most Famous Oil Paintings By Caravaggio
Caravaggio’s paintings were transgressors in the eyes of his contemporaries, according to scholar Mieke Bal. The Italian artist worked a lot with the contrast between pleasure and suffering, illusion and reality, religion and myth. Moreover, he painted things that were seen as taboo. Caravaggio was indeed a rebellious provocateur. And his own life reflects this.
Caravaggio was born in 1571 in Milan and trained as an artist in Peterzano’s studio in 1584. After that, he moved to Rome in the 1590s and started his early career both as a painter and criminal. Author Felix Witting explains that Caravaggio committed a series of crimes. Some of these included violence and defamation, just to mention a few. Eventually, Caravaggio’s criminal life lead him to the seemingly accidental killing of Tommasoni in a gang duel in 1606.
This is when he moved to Naples under the protection of the Colonna family. Between 1607 and 1608, he tried to get a pardon in Malta from the Knights of the Order. With no luck, he returned to Naples after a short stop in Sicily. In a final act of despair in 1610, he goes to Rome to seek pardon from the Pope himself. Unfortunately, he died in transit.
The cause of his death was unclear for a long time. However, a recent study of his remains by Michael Drancourt and his colleagues confirmed that he died from sepsis. It seems a wound he sustained in Naples after a fight got infected and eventually killed him. Finally, artist David Reed believes it is important that we understand that Caravaggio is a famous painter for us today because he can be seen and appreciated despite his turbulent past.
Now that you understand more about the psyche and life experience of this artist, you will be able to appreciate his art better.
11. Basket of Fruit

c. 1599 | Oil on canvas | Biblioteca Ambrosiana (Milan)
I wanted to include this painting because it is a classic piece of Baroque art. During this period, still life became an increasingly popular painting motif. Throughout that movement, artists were trying to capture the realism of life. Still life paintings became staple pieces to show an artist’s mastery to achieve a likeness of the real deal.
Moreover, according to Felix Witting, this type of painting with natural elements is very prominent at the beginning of Caravaggio’s career, perhaps his inception point of genius. However, Witting also states that Caravaggio discovers very early on that, despite how good he is at this type of painting, it is not for him.
He didn’t feel any kind of emotion in this art form, so he moved away from it to work on human narratives. In fact, Caravaggio even shows rebellion in this otherwise perfect painting. If you look closely you will see that he has incorporated elements of decay, such as wormholes and fallen leaves, which do not meet the picture-perfect ideas of this era.
10. Judith Beheading Holofernes

c. 1598-1602 | Oil on canvas | Galleria Nazionale d’Arte Antica (Rome)
This painting shows the biblical passage from the Book of Judith where Judith gets the Assyrian general Holofernes drunk and then cuts his head off. Caravaggio decided to paint the most impactful moment: when Judith is severing the head. If you look around the scene and pay attention to the expressions, you get a much deeper feeling for the psychology of this painting.
Aside from the obvious surprise and agony of Holofernes, if you look at Judith, her expression includes disgust, struggle, and uncertainty. Her helper looks on intensely too, yet away from the scene. Perhaps she is watching in case someone discovers the gruesome scene.
According to Andrea Pomella, this is the first painting in a series of works where Caravaggio explores the tragic meaning of life. The striking realism and expression on the faces convey the anxiety of the painter.
Author John L. Varriano explains this is also the first painting where Caravaggio starts using incisions into the materials to carve contours, which reinforces the contrast between light and dark in his tenebrism style.
9. Supper at Emmaus

1601 | Oil on canvas | National Gallery (London)
The Gospel of St Luke inspired this scene. This is the moment when, after his resurrection, Jesus appears to his disciples in the town of Emmaus. Moreover, according to Larry Keith, this is one of Caravaggio’s most highly touched up paintings and required a great amount of planning and preparation. Overall, we can see a more sophisticated development of his artistic skills.
If we compare this painting with the same version of the “Supper at Emmaus” in Milan, we notice that the London version uses light and contour more softly. There is more colour that helps create dynamism in the scene. The more elaborate composition creates the drama, instead of the stark tenebrism of the Milan version. According to Giulio Bora, this is because, in the London version, he borrows from the mannerism techniques we can see in Michelangelo or Raphael.
8. The Taking of Christ

1602 | Oil on canvas | National Gallery of Ireland (Dublin)
According to Andrea Pomella, the dramatism of this scene shines through the entangling of the bodies in the painting. Even though there is no clear setting or background to this scene, the figures alone and the drama are sufficient. This is the key moment when Judas betrays Christ at the garden.
The figures, from left to right are John, Jesus, Judas, who has just kissed Christ, and three Roman soldiers. Finally, there is a man holding a lantern, which is the point of light that Caravaggio uses for his tenebrism technique in this scene.
On a final note, this painting was believed to be lost for about 200 years. At the end of the 17th century, it was accidentally attributed to one of Caravaggio’s Dutch followers. This happened during the inventory taking of a large art collection that hosted this painting, so it’s origin was mixed up.
Thankfully for us, the senior conservator of the national gallery of Ireland, Sergio Benedetti, found it amongst the collection of some Jesuit priests in Dublin in the 90s and expertly identified it as an authentic Caravaggio.
7. Amor Vincit Omnia

1601-2 | Oil on canvas | Gemäldegalerie (Berlin)
The theme of the painting is clear: love conquers all. Here we see Cupid trampling over items related to reason, science, and war. This is, in fact, a fairly common subject of the time, but Caravaggio’s twist turned it into an instant classic.
We know that Caravaggio worked with a model for this painting, and the realism showcased here is almost photographic. In fact, according to Bradford Kelleher, there is a clear element of sculptural work in the creation of this piece and its structure. And David Stone notes that there is also a clear example of Caravaggio’s irreverence towards classicism.
If we look at this Cupid, he is charming but far from the beautiful god of ancient history. He has crooked teeth and appears incredibly childish, which is very far removed from the angelic and platonic Cupid of the Renaissance and ancient Rome.
6. Bacchus

c.1596 | Oil on canvas | Uffizi (Florence)
Although depictions of the classical gods were popular during the 1500s and 1600s, this painting of Bacchus is not conventional. According to Witting, Caravaggio painted the god as an androgynous figure. Moreover, the gesture and posture of Bacchus are actively engaging with the viewer: offering them a cup and inviting them to rejoice in the terrestrial pleasures.
Furthermore, Kelleher and Gregory state that this is a painting where we can see better than anywhere else in Caravaggio’s portfolio the impact the Cinquecento influences from artists in Brescia, Italy. Moreover, they explain that the tri-dimensionality and illusion effects here are direct borrowings from painters such as Moretto and Salvodo.
Art historian Ann Sutherland Harris states that this is the most polished out of all the half-length paintings of young men that Caravaggio did during his early career. In addition, she points out this is one of the few paintings that was never copied. She also proposes that the deviation from the traditional depiction of Bacchus may suggest that, perhaps, Caravaggio didn’t intend to paint the god himself, but someone dressed up as him.
5. Narcissus

1597-99 | Oil on canvas | The Galleria Nazionale d’Arte Antica (Rome)
According to Mary Ann Mattoon, this is another painting by Caravaggio that transforms art and the way we see this story of Narcissus. The trick is all in the water. Caravaggio uses his mastery of light and shadow, along with his realism of movement and form, to create two parallel images of narcissus. One stands in the light, which is the Narcissus that contemplates his reflection. The other one is the darkness of the water that will bring his doom.
Mattoon states that in other paintings, water had traditionally been used as a direct mirror or calming effect, but here Caravaggio achieves troublesome anguish that drives the narrative. Moreover, due to the composition of this painting, we have a general sense of fragility and lack of stability.
You might also see that the centre of gravity is off balance. So if you view this painting in person and feel a little dizzy, lightheaded, or slightly off, don’t worry, this is normal. Just take a moment to sit down; you’ve fallen victim to Caravaggio’s mastery of perception and drama.
According to John Varriano, these mythological topics, particularly those where there is one single figure, give us a glimpse into Caravaggio’s mind. He argues that although the motives may be borrowed from myth, pieces such as narcissus have also a sense of self-expression. Arguably, one could read that this is a moment of acknowledgment from Caravaggio to himself, realising his own troubled life and the darkness that surrounded him.
4. The Cardsharps

c.1594 | Oil on canvas | Kimbell Art Museum (Fort Worth)
If there is a painting that represents the actual life that Caravaggio lied beyond his paintings, it is this one. The picaresque that exudes throughout his life story comes across here, as he paints these people playing cards. Just two people in the painting are playing tricks on the other naïve person.
According to Sybille Ebert-Schifferer, Caravaggio knew the literary fashions of the time. And as it often happens, one art method borrows from another. Aware of the picaresque novels from Spain that were ever so successful, with ruffians, tricksters, and the ordinary people as their protagonists, he would have thought this would also make perfect characters for his paintings. According to Ann Sutherland Harris, if we look closely, we will notice that the characters in this painting are similar to those in “The Calling of St Matthew.”
In addition, we know that Caravaggio liked gambling. In fact, it is likely that many of his fights happened because of games, debts, and egos hurt in the process. Above all, we must understand pieces like this, acted as social windows and commentaries of the world around people such as Caravaggio and their contemporaries. They are accounts of people who don’t often get an abundant historical record, which helps us understand periods of history in a more holistic manner.
3. The Calling of St Matthew

1599-1600 | Oil on canvas | San Luigi dei Francesi (Rome)
This painting is interesting because, according to Juliet Benner, it is full of spiritual power. The huge size of this painting in its current location (which is a relatively small chapel) means the message is impossible to miss. The pointing hand of Jesus to the tax collector Levi, who will later become Matthew, is a clear and commanding invitation to join Christ.
Marjorie Cohee Manifold explains that, if you notice the window on the upper area of the painting and follow the light to the pointing hand, this helps understand the story. Benner notes that the darkness of the room symbolizes Levi/Matthew’s soul, while the piercing light is the clear road to salvation. Furthermore, Pomella states that this was Caravaggio’s first prominent commission in the city of Rome.
And Witting explains this painting caused a commotion in Rome at the time. This is particularly easy to see if we think that this painting was originally an altarpiece. If you pay attention, you can see how the five characters were actually gambling, and as Jesus comes to announce his mission, the scene breaks up. This would have looked rather out of place in a church despite the topic of conversion.
2. Medusa

1597 | Oil on canvas mounted on wood | Uffizi (Florence)
Here Caravaggio painted the very moment where Perseus cut off Medusa’s head. Mieke Bal states that, unless you see this Medusa in the flesh, her gaze gets lost in translation. In this digital version, Medusa seems to be looking away and terrified at her fate. However, on the convex surface of the shield where it was originally painted, it becomes harder for us to know exactly where she is looking or with what intent.
Bal explains that Caravaggio played a lot with the concept of spatiality, often confusing and baffling his audience. Unfortunately, this is one of the many issues we get with decontextualized art. Either way, the expression of absolute shock is as realistic as it gets, and so is the perfect depiction of the snakes in Medusa’s head.
By now you’ve also seen a recurring theme of beheading as a running topic in Caravaggio’s paintings. As historian Thomas Puttfarken explains, this is a reflection of his internal struggle and violence, which he develops through these scenes that show torture and martyrdom in a very baroque and Christian dual nature, just like his life.
Finally, this piece is also important because of Caravaggio’s patron. This was the second artwork that Cardinal Francesco Del Monte commissioned from him. In fact, it is thanks to the patronage from this cardinal, diplomat, and art collector, that Caravaggio found his place as a stable artist despite his run-ins with the law. Without the help of people such as Del Monte, Caravaggio may have struggled to keep up his momentum.
1. Conversion On the Way to Damascus

1601 | Oil on canvas | Santa Maria del Popolo (Rome)
This painting perfectly shows Caravaggio’s famous chiaroscuro and tenebrism techniques. This is highlighted once again by the diagonal line creating perspective and directing the light. You can see this from the rump of the horse to its muzzle. Moreover, authors George Van Kooten and Antonio Cimino point out that the way Caravaggio uses the light to shape St. Paul gives the impression that the conversion has already happened.
Saul is now Paul because of the grace of the Lord. Light surrounds his whole body. This suggests the mystical powers have now done their job. Therefore, Paul is ready to become a follower of Jesus.
To fully understand this painting, we need a little bit of biblical knowledge. The motive of St. Paul and his conversion is very powerful because it is the ultimate tale of redemption. Saul (Paul’s name before converting) was a Pharisee who actively discriminated against Christians. His conversion demonstrated that even the enemies of God can find their way into the path to heaven.
Finally, the fact that Caravaggio had the opportunity to make paintings for the Pope’s treasurer, Tiberio Cerasi, is remarkable on its own. It suggests that despite his troublesome background, his talent was—at least at that moment—still outshined his criminal activities. According to the Menzies, he was like a “rock star.” In which case, even the most powerful men in Rome could look momentarily look the other way to obtain a masterpiece.
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