Police mugshots are among the most familiar and revealing of portraits, celebrated internationally in art galleries and coffee table books. But what about less stark images of criminals? This month sees an exhibition of portrayals of British gangsters past and present, painted by a young artist whose aim is to capture the likenesses of some of our most notorious criminals for posterity.

“Mad” Frankie Fraser, Charlie and Eddie Richardson, Chris and Tony Lambrianou of the Krays’ gang, Freddie Foreman, Bert “Battles” Rossi, Roy “Pretty Boy” Shaw and Linda Calvey, jailed for killing her lover, are among those included in an exhibition that represents a year of work by Cambridgeshire-based painter Charles Delafeld. Many of that crew not already in the great holding cell in the skies will be attending the event at the Arts Theatre Club in Soho, London, itself once an illegal drinking den.

Delafeld, 29, says his interest in portraiture was prompted by a school trip to Florence. “At the age of 16, I just wanted to be Caravaggio!” he says over a mocha in a Cambridge cafe. His mother was a chef who liked to paint, his stepfather a taxidermist. Delafeld had wanted to go to art school but “went off the rails a bit” when his mother died while he was still at school.

Roy “Pretty Boy” Shaw by Charles Delafeld.

After a brief career selling Cambridge university goods, he started painting portraits professionally from photos. One of his first works was of the former archbishop of Canterbury, Rowan Williams: “He looks like what he is – he could be a Renaissance painting.” His move to the sinners’ end of society started when he painted Steve Tully, a Kray twins protege, and his work was last year used as the cover of Dodger, Tully’s memoir.

This led to interest from elsewhere in the underworld and he next painted a 94-year-old “Battles” Rossi, a key figure in 1950s gangland London whose memoirs come out this year. “I wanted to do portraits of an era that was fast disappearing,” says Delafeld. He has now created images of more than 20 such figures, leading to the Gangland Art exhibition.

There is a long history of overlap between British art and crime, which reached its apotheosis in the 1960s. Francis Bacon and Ronnie Kray hung out together not least because the Kray twins ran the gaming club Esmeralda’s Barn, where Bacon ran up hefty debts; he cancelled one exhibition because he did not want the Krays to realise quite how much he was making from his work.

Ronnie, who fancied himself as an artist, later corresponded with Bacon from Broadmoor; a brief letter from the artist, sent in 1989, fetched £7,400 at auction 20 years later. Bacon’s muse and partner was petty crook George Dyer. And the scar-faced gentleman in Lucian Freud’s 1964 portrait, A Man and His Daughter, was later described by the artist as being of “a very clever bank robber”.

Chris Lambrianou approves of his portrait by Delafeld. Now 78, he was jailed for 15 years for disposing of the body of Jack “the Hat” McVitie but found God in prison and on release worked with the Ley Community in Oxfordshire, a rehab centre that helps addicts, some referred from prison. He is wary of glorifying old gangsters – “the Krays were not legends but losers” – but will be attending the exhibition and thinks Delafeld has caught his likeness,using a photo taken at the funeral of “Mad” Frankie Fraser.



Chris Lambrianou by Charles Delafeld.

“I think the painting is quite realistic,” says Lambrianou. “It captures the moment: reflective and sad, the end of a journey, the parting of ways.” He is relaxed about being part of a rogues’ gallery. “I see my picture all over the internet, sometimes with a machine gun added. You can’t do anything about it. It’s today’s world.”

He remembers Bacon from the Kray years: “He seemed like a decent chap to me – but then everyone seemed like a decent chap in front of the twins.” Most of Delafeld’s portraits are, inevitably, of men but there will be a couple of women. One is Linda Calvey, who spent 18 years in jail for the murder of her lover, Ronnie Cook, in 1990 and is routinely described by the tabloid press as “the Black Widow – because all her men end up dead or in jail”.

Her first husband, Mickey Calvey, was shot dead by police during an attempted robbery in 1978. Calvey was accused of paying Daniel Reece £10,000 to kill Cook, although it was claimed in court that she finished off the job. She later married and divorced Reece in jail and still denies the murder.

Delafeld has also painted Harry Roberts, who shot dead three police officers in 1966, although that picture will not be appearing in the exhibition. So what about the morality of immortalising or glorifying men who have carried out murder? “I don’t agree with putting them on a pedestal and I don’t condone what they have done,” he says. “But they are still a piece of history.” What if, say, Peter Sutcliffe, “the Yorkshire Ripper”, asked to be commemorated. “No, I wouldn’t do that.”

Of other faces Delafeld would like to commemorate, the late Howard Marks, often described as Britain’s best-loved drug smuggler, is top of the list. After that, he says, he wants to shift to the other side of the law and paint judges. He says the link between art and crime is strong in numerous ways. “For instance, The Scream has been stolen a number of times.” Thieves briefly took Edvard Munch’s famous picture from its Norwegian gallery home in 1994, and again for two years in 2004.

Norman Buckland by Charles Delafeld

He admires the work of David Henty, who was jailed for forging passports. He turned to art in prison and now describes himself as a “fine art copyist”, reproducing convincing duplicates of work by everyone from Modigliani to Van Gogh.

Not that Delafeld is the only person to have put faces to the underworld. Nick Reynolds, the son of the late great train robber Bruce, is both an artist and a musician (a member of the Alabama 3, who created the Sopranos theme tune Woke Up This Morning). He made a death mask of John Joe Amador, who was executed in Texas in 2007 and a “life mask” of his late father, which is now in Highgate cemetery. His subjects have also included Frankie Fraser, Roy Shaw, Tony Lambrianou, Howard Marks and cat burglar Peter Scott – whose last conviction was for involvement in stealing Picasso’s Tete du Femme – which he has shown in an exhibition called Cons to Icons.

But Reynolds thinks this may be a dying art. “Thanks to the cod science of phrenology in the 19th century,” he says, “it became commonplace to cast the heads of executed criminals to see if criminal traits could be observed in features and skull shapes. Notable cases include the infamous bushwhacker Ned Kelly. With the debunking of phrenology, the practice declined and the masks became macabre curios. Nowadays most people prefer not to dwell too much on their mortality, and reminders of death have fallen out of fashion.”

There is also a declining number of criminals who would like to be commemorated for other reasons. As David Bailey has said of his famous photo of the Kray twins: “Their big mistake was posing for me. If you’re a real gangster, nobody knows who you are.”