Caravaggio paintings that broke all the rules

Learn more about Caravaggio and how his paintings, although controversial, broke paradigms.

The story of Michelangelo Merisi—better known as Caravaggio—is full of talent and controversy. This master of the Italian Baroque defied convention, both in his artistic practice and in his personal life. Being a man with a difficult personality, his work fell out of favor after his death in 1610 and was not appreciated by the public again until the middle of the 20th century.

Born in Milan, Caravaggio moved to Rome in his twenties and joined a circle of wealthy patrons who furthered his career. In an age where figures in paintings were idealized, Caravaggio using living models and portraying them realistically was groundbreaking. His use of realism and chiaroscuro technique make his paintings radiate a certain unprecedented psychological drama. Caravaggio was never afraid to take risks, and this is why anyone who was part of his life could end up in one of his paintings. This includes his disciple—and his lover—Mario Minniti, who appears in several paintings, including Bacchus, now in the Uffizi Gallery in Florence. In this piece, Minniti appears dressed as the god of wine, a representation of youth that invites the viewer to join the party.

Although many others would have preferred to follow the rules, Caravaggio’s artistic convictions were unshakable. In fact, many of his paintings commissioned by the Catholic Church were rejected, as they did not conform to the aesthetic standards of the time. Fortunately, Caravaggio always had a legion of loyal collectors ready to snap up any painting he offered them.

Historians tend to focus a lot on Caravaggio’s explosive temper, which caused numerous fights and eventually a murder that led him to flee Rome. Artistically, however, Caravaggio is perhaps best known for his use of light and shadow. The high contrast between light and dark present in his paintings would influence later artists such as Rembrandt and Pedro Pablo Rubens. An entire generation of painters (especially in Northern Europe) known as Caravaggisti was inspired by his use of shadows. Let’s examine what makes Caravaggio and his art so revolutionary by taking a look at some of his most fascinating paintings.


Bacchus, the mythological god of wine, was a popular subject among painters, but none had portrayed him with Caravaggio’s realism. This painting, painted on the painter’s arrival in Rome, is actually a self-portrait. Known as sick Bacchus, Caravaggio does himself no favors when it comes to portraying himself. Here it is already demonstrates his desire for realism, even if the results can be unpleasant.

Caravaggio’s Bacchus has pale, grayish skin, and few would think him handsome. However, as was typical of the Baroque painter, Caravaggio was not interested in idealized portraits. The oil painting, done for one of his earliest patrons, was a kind of business card showing his ability to create still lifes as well as portray classical subjects in complex poses.


You may be wondering: what is revolutionary about a simple fruit basket? In the case of Caravaggio’s Basket of Fruit, the painting is truly transcendental. Although still lifes were already becoming popular in Northern Europe, things were different in Italy. Flower or fruit baskets were often incorporated into larger scenes, but were never the main subject of the work. Or, at least, that’s how it was before Caravaggio.

Basket of Fruit was a gift from one of Caravaggio’s early patrons, Cardinal Francesco del Monte, to Cardinal Federico Borromeo, a great admirer of Flemish painters. Having seen Caravaggio’s talent for still life as part of other works such as his paintings of Bacchus, it would have been natural to ask for a piece featuring these decorative elements. It is currently in Milan, and today it is considered the first Italian still life.


After a few years in Rome mingling with high society, Caravaggio began to receive important commissions in the city’s churches. Without letting institutional expectations or traditional iconography pressure him, the rebellious artist used these projects to experiment and show his unique point of view. The Calling of Saint Matthew, which is still in its original location, remains one of Caravaggio’s most famous paintings. The informal and natural posture of the figures represented an enormous change against the idealism of Mannerism. Dressed in contemporary clothing, the characters seem to be taken from a genre scene, not a traditional religious painting.

But the real genius of the painting is found in Caravaggio’s use of light and shadow—a characteristic element of his style. Following the architecture of the chapel and its windows, the sunlight enters and follows the hand of Christ, who points to Mateo. The light not only creates more drama but acts as a metaphor for the hand of God, asking Mateo to join him.


Caravaggio’s next big project saw him create two paintings for the same chapel. Although both are still in the church of Santa Maria del Popolo in Rome, neither of the two paintings currently on view was the artist’s first version. In fact, both paintings were rejected by the patron, forcing Caravaggio to do them again.

Although the exact reason why the Crucifixion of Saint Peter was rejected is unknown, his second version is still full of daring elements. Caravaggio was known for using ordinary people as models, something unheard of at the time, and it was shocking to see figures in a religious scene so realistic. Here Peter looks like an ordinary man, not a glorified saint, and one of his executioners even has dirty feet. Caravaggio put these biblical characters on the same level as ordinary citizens, instead of elevating them on a pedestal—a controversial decision at the time.


Directly opposite the Crucifixion of Saint Peter is another striking painting by Caravaggio, The Conversion of Saint Paul on the Road to Damascus. The first version of this painting was also rejected—although both were acquired by avid Caravaggio collectors. The oil painting on display today showcases Caravaggio’s masterful use of light, with a warm glow taking over Pablo as he falls from his horse, emerging from the darkness.

The performance once again breaks with tradition. Whereas Renaissance and Baroque paintings of the scene often included a horse, here Caravaggio has made the animal—and its rear—a dominant element of the composition. It was a controversial choice that, it is said, provoked this exchange between the artist and an ecclesiastical authority: “Why have you put a horse in the center and Saint Paul on the ground? “Because if!” “The horse is God?” “No, but he is under the light of God!”