Michelangelo Merisi, known as Caravaggio after the small town in Northern Italy where he grew up, was a prototypical bad boy. A rebel artist with a tempestuous 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.
In 1500s Italy, art mostly glorified Biblical stories and the saints. Like many artists then, 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 brought in an element of realism that freaked out the establishment.
His paintings do depict the expected stories and Biblical scenes—but with his own delicious twist: He painted the Virgin Mary with the face of a known prostitute, or with a little too much cleavage for comfort (as in his Madonna of Loreto, left). He dared to portray the Madonna as a normal woman, and even showed her bare feet. Horrors! "He had to know what the reaction was going to be, but it was like he couldn't help himself," says writer Tiffany Parks (ThePinesofRome.blogspot.com). "He couldn't sell out." Caravaggio wanted to show the truth, and his truth often involved Roman prostitutes.

CARAVAGGIO'S WHORES Who were Caravaggio's models? 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.
Fillide and Anna were both born in Siena, and they met as young girls, after their fathers died, leaving their 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 waitressed in a tavern. The Bianchini family—including daughter Anna, who was the same age as Fillide—shared the carriage.
You might imagine the girls sizing each other up during the cramped ride to Rome, but they quickly realized 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. The girls were about 13 years old.
It's unclear when the twenty-something Caravaggio met the girls, but by the time they were 16 or 17, they'd begun modeling for him. Anna has a sad story, which I write about on my blog, searchingforbernini.com. Here, I'll focus on the fierce Fillide, of whom he painted a famous portrait (above) around 1598 that unfortunately was destroyed during World War II.
Also in 1598, both Fillide and Anna posed for the reckless but brilliant artist's Martha and Mary Magdalene. Fillide is on the right as Mary, while Anna likely sat for Martha.
The painting exemplifies the irony in many of Caravaggio's works: He used prostitutes to represent the moment Mary Magdalene turned away from prostitution and was telling her sister Martha, who had devoted her life to God. While the women are depicted realistically, down to Fillide's slightly crooked finger, neither she nor Anna was likely to give up her work to follow the Almighty.
Fillide seemed resigned to her life as a prostitute and toughened up accordingly. As Graham-Dixon writes, Caravaggio later painted her as she really was, "tough, passionate, with a capacity for violence." In one instance in 1600, she got arrested for assault with two other prostitutes, writes Graham-Dixon. She reportedly attacked another whore with a knife and had to be restrained. One witness said Fillide shouted at the woman, "Whore, I'm going to scar you everywhere."
Just two years earlier, Fillide had posed for Caravaggio's fearsome and beautiful St. Catherine. She'd also modeled for his visceral and bloody Judith Beheading Holofernes. But the realism of paintings like these horrified the establishment. They were too real for comfort. Locals may have read in the papers that Fillide was often in trouble with the law and recognized her in the painting.
What's more, 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. Her assault arrest in 1600 may have involved a fight between the women over Ranuccio.
A COURTESAN'S LIFE Fillide disappears from Caravaggio's art for a while after 1599, but she was by that point a sought-after courtesan. She had earned enough to leave Anna behind, and had begun training other courtesans—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). She may also have taught her trainees how to avoid pregnancy: Like cutting a lemon in half, squeezing out the juice and using it as a 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, for whom her portrait may have been painted. Her elevated social status could have put an end to her working with Caravaggio. But in 1604's The Entombment (now in the Vatican's picture gallery), Fillide, now 22, reappears, posing for both Mary Magdalene and another woman, who weep beside the Madonna.
A Deadly Rivalry Two years later, on the evening of Sunday, May 28, 1606, Caravaggio killed Ranuccio Tomassoni. Could Fillide have played into the deadly animosity between the two men? Perhaps. Graham-Dixon argues that Caravaggio moonlighted as a pimp—what better way to be sure he had models at his disposal? Had he tried to steal Fillide from Ranuccio, inflaming a rivalry between the two men? The usual story says the men fought over a tennis match, but Graham-Dixon disagrees, writing that it was only a ruse to set up a duel over slighted honor.
Caravaggio fled Rome, and sadly died in 1610 while on his way back to the city having finally secured a pardon. Anna had died in 1604, Ranuccio followed and now 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 at the time—25 years—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 off. She left some money to religious institutions dedicated to the Virgin, as well as to the Convertite—religious houses where reformed prostitutes could go to escape life on the street. But she asked that the portrait Caravaggio had made of her when she was a young girl of 17, and now was in her estate, should go to her former lover, Giulio Strozzi.

Lisa Chambers United States

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