Without men there would be no prostitutes.

I’m starting this entry with a portrait of a man, the painter Caravaggio. And without Caravaggio, we would know nothing about these women.

Michelangelo Merisi, known as Caravaggio after the small town in Northern Italy where he grew up, was a prototypical bad boy, as I wrote in a story first published by Dream of Italy in April 2015. A rebel artist with a tortured personal life who lived in Rome from 1592 to 1606, Caravaggio created paintings unlike any that had been seen before: Dark, moody and startlingly naturalistic, he painted as he lived—in the most dramatic and risky fashion.

Today, his reputation and life story lives on through his work, which is still revered in museums around the globe, and through movies, biographies, like Andrew Graham-Dixon’s 2011 best-seller, and novels, like the engrossing A Name in Blood by Matt Rees, that capture the agony and ecstasy of the artist’s life.

In the 1500s, art was focused on glorifying the stories of the Bible and the saints. Like many artists in the late 1500s and early 1600s, Caravaggio often hired prostitutes to pose for his paintings. But unlike most artists who used the women’s features to paint works that conformed to the religious or moral expectations of the day, and conveyed a kind of ethereal beauty, Caravaggio took that tradition and brought in an element of realism that freaked out the establishment.

The Italians thought, essentially, that he was biting his finger at those traditions—a terrible insult.

His paintings do depict the expected stories and Biblical scenes, but he painted the Virgin Mary with the face of a known prostitute, or with a little too much cleavage for comfort. He dared to portray the Virgin as a realistic, normal woman, and even show her bare feet! Horrors. As writer Tiffany Parks (ThePinesofRome.blogspot.com) told me, “He had to know what the reaction was going to be, but it was like he couldn’t help himself. He couldn’t sell out.” Caravaggio wanted to show the truth and his truth often involved Roman prostitutes.

Who were Caravaggio’s prostitutes?

Fillide Melandroni became a well-known courtesan, sought after by the elite. Anna Bianchini dreamed of such success but her life came to a tragic end. There were others, too, like Maddalena Antognetti, known as Lena, who likely worked as a prostitute in Piazza Navona and may have been Caravaggio’s lover at the time of his exile, but I’ll save her for a later post.

In Rome, street walkers often got rounded up,
whipped or tortured as the authorities tried to convince
them to change their wicked ways.

Fillide and Anna were both born in Siena, and they met as young girls when they were moving to Rome under similar circumstances. Both of their fathers had died, leaving the families in dire financial straights. According to Andrew Graham-Dixon’s stellar biography, Caravaggio: A Life Sacred and Profane, Fillide traveled with her mother and brother to Rome where her aunt worked as a waitress in a tavern. Sharing the carriage to Rome with the Melandronis were members of the Bianchini family—mother Sibilla, and her three children, including daughter Anna, who was the same age as Fillide.

You might imagine the girls sizing each other up during the cramped ride to Rome, but quickly realizing how much they had in common as their mothers talked about their shared misfortune and what awaited them in the city. The two families found lodging together, and before long the mothers “put their daughters to work as prostitutes,” writes Graham-Dixon. Anna and Fillide were about 13 years old.

No doubt it was a miserable and terrifying existence. The girls worked to support their families, but as Graham-Dixon reports, they were arrested together when caught out after curfew a year into their new career. The charge was suspicion of solicitation.

It’s unclear when Caravaggio, who would have been in his twenties, met the two girls, but by the time they were about 16 or 17, he’d begun using them as models. Red-haired Anna likely posed for two early works by the artist—The Rest on the Flight to Egypt and The Penitent Magdalene. Both paintings can be seen in the Palazzo Doria Pamphilj museum in Rome. They’re beautiful depictions, and much softer than his later, darker work.

But what shocked viewers at the time was that Anna, who posed as the Virgin and the Magdalene, was recognized as a prostitute in Rome, which even today can seem like a small town. Caravaggio had done nothing to hide the fact of who she was, but sticking to his belief in realism he depicted her as she appeared to him: humble, repentant, and with a tear slipping down her cheek. As Graham-Dixon writes, she looks truly like “a person in turmoil.”

And she may have been, according to an excellent walking tour I took from storytellingrome.com. Our guide Massimo said that Anna wasn’t acting but truly shedding tears because she’d come to Caravaggio’s studio after having been flogged by the authorities. While Rome (and the Church) looked the other way when it came to high-class courtesans who could entertain visiting heads of state, street walkers often got rounded up, whipped or strung up by their arms and tortured as the authorities tried to convince them to change their wicked ways. Not only that, if they survived the beating, they were then forced to ride around Rome on a donkey, with their dresses pulled down to show their cuts and bruises, as a deterrent to other would-be working girls.

But Anna and Fillide remained undeterred. Fillide may have been enjoying her steady income and Anna probably didn’t have a choice. The two girls both posed for the recklessly brilliant artist sometime in 1598 for his Martha and Mary Magdalene. Mary is on the right, modeled by Fillide, while Anna likely sat for Martha, on the left. The painting is a good example of the irony in many of Caravaggio’s portraits: He used prostitutes to represent the moment Mary Magdalene decided to turn away from prostitution, and was telling her sister Martha, who had already devoted her life to god. While the women are depicted realistically, down to Fillide’s slightly crooked finger, neither of them was likely to give up her work to follow God.

Posing for Caravaggio may have given the girls a brief respite from their lives on the streets. But Fillide, for one, seemed resigned to the life and she toughened up accordingly. As Graham-Dixon writes, Caravaggio later painted her more as she really was, “tough, passionate, with a capacity for violence.”

She posed for his gorgeous St. Catherine, who is at once fearsome and beautiful. And she modeled for his famous Judith and Holofernes, where Fillide’s own penchant for violence may have come in handy. But the realistic results of paintings like this one horrified some members of the elite establishment. It was too real for comfort.

Locals may have read in the papers that Fillide was often in trouble with the law, and once had been charged for having a raucous Mardi Gras party at her house. Her pimp was likely Ranuccio Tomassoni, and here the plot thickens. Tomassoni is the man Caravaggio murdered in 1606, forcing the artist to flee Rome, never to return.

A scar on the face—sfregio—was a known mark
of a fallen woman in Italy.

In 1600, Fillide got arrested for assault with two other prostitutes who also worked for Tomassoni, writes Graham-Dixon. She reportedly attacked another whore with a knife and had to be restrained. In testimony against Fillide, one witness reportedly said Fillide rushed at the woman shouting, “Whore, I’m going to scar you everywhere.”

A scar on the face—sfregio—was a known mark of a fallen woman in Italy. (Gian Lorenzo Bernini sent one of his servants to slash the face of his mistress when he caught her cheating on him with his own brother. Hey, what else could he do?) The incident shows how violent the life of a Roman prostitute could be. Remember Fillide’s bent finger? That may have come from one of her brawls.

Fillide disappears from Caravaggio’s art for a while after 1599, but she was by that point a sought-after courtesan, perhaps due to Ranuccio’s connections with the grand Farnese family (I’ll write about Giulia Farnese in a later post). Fillide earned enough to leave Anna behind, and trained other women hoping to enter the upper levels of courtesan life—teaching them the art of conversation or, more likely, the ways to make love (a popular catalogue from the times was published in the 1500s of 16 favorite sexual positions, including one called “the bell tower” the church’s only condoned position, known today as the missionary position). (For a clip from the film Dangerous Beauty, that explains what kind of training the courtesans went through, click here!)

She may also have clued her courtesan-trainees in on how they could avoid pregnancy. While for years women had tried things like drinking mercury, which didn’t turn out so well, they resorted to a simple, and less-deadly, answer: Cutting a lemon in half, squeezing out the juice and using it as a very primitive kind of diaphragm!

The dark-eyed, volatile Fillide may also have fallen in love with one of her patrons during that time, the Florentine nobleman Giulio Strozzi. Her elevated social status—and her continued work with Ranuccio—might have put an end to her working with the scrappy struggling artist Caravaggio.

But in Caravaggio’s 1604 painting The Entombment (now in the Vatican’s picture gallery), Fillide, 22, reappears, and she posed for two different characters: Not the Virgin, but Mary Magdalene and a third Mary, who weep beside the Madonna. Perhaps she was on the outs with Ranuccio at that point.

But what of Anna? Most of what is known of her comes from legal records of the time, for she continued to get in trouble with the law—and continued to be a streetwalker. According to an Italian book on the subject, she “attended tailors, butchers and innkeepers.” She hadn’t achieved Fillide’s success.

It’s not clear if Anna continued to “attend” Caravaggio, but she came to a sad end. In 1604, according to storytellingrome’s Massimo, she drowned in the Tiber river. She may have been murdered. At the time, Caravaggio was under pressure to produce a painting of the Death of the Virgin, and stories of the time say he somehow had Anna’s corpse delivered to his studio where he used the bloated body of the poor street walker as the model for the dead Mary.

It was shocking for obvious reasons, but also because in the final painting Mary’s dress is hitched up and disordered to show her bare feet and her hair is a mess. If this was really Anna’s body dragged from the river, Caravaggio caught the realism of her death. But for people who wanted to see the peaceful, sacred end of the life of the mother of Christ, this wasn’t it. Massimo told us that Caravaggio may have painted the purported murderer into the picture as a dark, bearded figure in the background who’s showing very little emotion, unlike those around the body. But that may also be legend. Nevertheless, it was a sad end for Anna.

Two years after starting his Death of the Virgin (now in the Louvre), Caravaggio killed Ranuccio with a knife. With Anna gone, could Fillide have played into the deadly animosity between the two men? Perhaps. Graham-Dixon argues that Caravaggio likely moonlighted as a pimp—after all, what better way to be sure he had models at his disposal? Having lost Anna, had he tried to steal Fillide from Ranuccio, setting up a rivalry between the two men? The usual story says the men fought over a tennis match, but Graham-Dixon disagrees, writing that the match was only a ruse to set up a duel over slighted honor.

Ranuccio was dead and Caravaggio exiled for murder. He died in 1610—perhaps of malaria, perhaps following an attack on him by the Knights of Malta (which is a whole other post!)—while on his way back to Rome having finally secured a pardon for Ranuccio’s murder.

Fillide was the last woman standing in this strange circle of friends and rivals. Surprisingly, given her life and the life expectancy of most prostitutes—which was 25 years, about the age Anna was when she died—Fillide lived into her late thirties.

By 1618, Graham-Dixon reports she had her own house, which may have looked like one of the few courtesan’s houses still standing in Rome. But she was very ill, perhaps with a venereal disease, and she died in July of that year.

Fillide left a will behind in which she stated she wanted her estate sold. She left some money to religious institutions dedicated to the Virgin, and a good amount of her estate to the Convertite—religious houses where reformed prostitutes could go to escape life on the street (if the house would take them in, which wasn’t always the case). But she asked that the portrait Caravaggio had made of her when she was a young girl of 17 should go to her former lover, Giulio Strozzi.

Ciao!