Severance package … detail of David with the Head of Goliath by Caravaggio. Photograph: Archivo Iconografico/SA/Corbis. Click to enlarge.
You can't make a top 10 of criminal artists without putting Michelangelo Merisi, called Caravaggio after his hometown, up top. There is a cutting quality to Caravaggio's art, a tough cinematic realism that puts you right in the mean streets of early 17th-century Rome. And on those mean streets, he was a dangerous man. Aggressive, ill-tempered and given to carrying a sword, Caravaggio was constantly in trouble for everything from hitting waiters to slandering rivals. Eventually, inevitably, he killed a man in a fight on a piazza and had to flee Rome. On the run he painted works that seem full of guilt, including his dark self-portrait as the severed head of Goliath in which his eyes despair of his sins.
2. Benvenuto Cellini
But Caravaggio's reputation as a criminal is arguably exaggerated. Street fights were not rare in his time and he shows penitence in his art. Not soBenvenuto Cellini, who in the 16th century killed repeatedly without remorse and without being punished. He stabbed his brother's murderer to death with a long twisted dagger that he drove downward through the man's shoulder. He also killed a rival goldsmith and shot an innkeeper dead – and recounts all these crimes in his autobiography. He escaped being executed because he was so admired as an artist. In those days, geniuses really could get away with murder.
Graffiti is a Crime … a Banksy mural in New York City
Graffiti art is by definition a defiance of the law, and Britain's Banksy has made a brilliant career of painting and stencilling in places you are not supposed to. Part of his sucess is his ability to evade capture – a trial would presumably blow his famed anonymity. Yet the works that were once erased by angry councils and property owners are now regarded as precious treasures to be preserved, or broken off the building and sold.
4. Egon Schiele
In 1912 this dangerously erotic Austrian artist was arrested for supposedly having sex with a teenage girl. Schiele was 22 at the time – and the real motive for the arrest was a small town's horror that he was drawing his models in their underwear.
Stolen glance … Picasso in his studio at Vallauris in southern France. Photograph: AP
The greatest modern artist received stolen goods in the early 20th century when a criminal friend of a friend – the connection between them was the avant garde poet Apollinaire – stole some ancient Iberian statues from the Louvre. They ended up in Picasso's studio where he made good use of them, studying their primitive forms to use in his raw revolutionary art.
The Carmelite friar and Renaissance genius Filippo Lippi seduced a young nun called Lucrezia Buti. They had a son and daughter. Was 15th-century Florence scandalised by this outrageous defiance of ecclesiastical law? Not really. Lippi was a favourite artist of Cosimo de' Medici, the most powerful man in the city, and as a result he was never prosecuted for his crime. His illegitimate son Filippino grew up to become a great artist in his own right.
7. Olive Wharry
This early 20th-century British artist was sent to prison after she burned down the tea house at Kew Gardens. Wharry was a suffragette and is remembered more for her defiance of the law than for her art. Her gentle watercolours make a surprising contrast with her deeds of arson and self-starvation.
8. Shepard Fairey
The alleged vandal Shepard Fairey, at work in Copenhagen
This 15th-century artist is famous for his altarpieces bulging with fancy architecture, sinuous female saints and hyperrealistic images of fruit. His art was made for churches in eastern Italy and yet it seems more worldly than pious. In fact, the only reason Crivelli was in all these small cities decorating altarpieces for a living was that he was persona non grata in Venice after being convicted of a sex crime for sleeping with another man's wife.
This brilliantly gifted young Victorian artist was tragically struck by mental illness while touring Europe. Was his collapse the result of tensions between Victorian England and the sensuality of foreign climates? When he came home, he stabbed his father to death and spent the rest of his life in prisons and mental institutions where he painted fantastic fairy scenes of bizarre intensity. He died in Broadmoor.
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