They were ’s most infamous gangsters who terrorised the East End with armed robberies, extortion and two high-profile m, but it turns out that also had a fondness for art.

While still at large, the brothers commissioned friend Paul Lake to paint an oil portrait of themselves, which had to be repeated twice after a bullet went through Reggie’s head and a knife slashed through Ronnie’s heart.

After the Krays twins were finally caught and jailed in 1969, they joined art classes at Parkhurst prison on the Isle of Wight, where they produced several works of their own, as well as self-portraits. Some of their canvasses will be auctioned on Friday at Sloane Street Auctions in central London, with the oil portrait expected to fetch up to £20,000.

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But they aren’t the only famous criminals who have left their own image on canvass. From serial killers to death cult leaders and dictators, here are some of the others…

One of the worst serial killers in American history, John Wayne Gacy was known as the “Killer Clown” due to the fact that he performed as “Pogo the Clown” during the day.

At night, however, he prowled the streets of Chicago and murdered 33 young men and boys between 1972 and 1978, raping, torturing and strangulating them before burying them around his house.

While on death row before his execution in 1994 Gacy painted pictures of Elvis, Jesus, the Seven Dwarfs, as well as a terrifying self-portrait dressed as a clown.

In 2001, musician Nikki Stone bought the painting, but decided it was cursed after both his dog and his mother were diagnosed with cancer soon after. The painting now belongs to paranormal investigator Zak Bagans, who owns and operates his own Haunted Museum, housing creepy items like Charles Manson’s hospital gown as well as John Wayne Gacy’s brain.

Before he became one of history’s most murderous dictators, Adolf Hitler was an awkward teenager who wanted to become an artist.

Aged 18, he went to Vienna to study fine art, but was rejected twice by the city’s Academy of Fine Arts after being told he wasn’t a talented enough artist, so resorted to painting watercolours and selling them to tourists.

One of the watercolours shows the future Fuhrer sitting alone on an old stone bridge, along with a cross and the initials AH above the figure. The painting, along with 12 others by the Nazi monster, was discovered by a US Army sergeant in 1945 when he was stationed in Essen, Germany, who kept them out of sight for decades.

An art expert who analysed the painting on wrote: " I would think that the person who created it was lonely and felt isolated, perhaps depressed or pensive due to the drab colours and overcast sky. The fact that the figure is placed near the edge rather than the centre makes me wonder if there were feelings of hoping there'd be room for others who haven't come and a feeling of waiting, or maybe feeling uncertain about themselves."

The painting fetched £10,000 - ten times its reserve price - when it was auctioned in Shropshire in 2009.

One of America’s most infamous criminals, in the summer of 1969 cult leader Charles Manson ordered his followers to commit a serious of heinous murders that terrified Los Angeles and shocked the country.

Over the course of two nights, ‘Manson Family’ members brutally killed seven people, with crime scenes marked with bizarre and disturbing messages written in victims’ blood. They included pregnant actress Sharon Tate, wife of famed film director Roman Polanski, who was was killed in her own home along with four others.

Initially given the death penalty in 1971, his sentence was later commute to life in prison in 1972. While behind bars he took up painting to pass the time, including a portrait of himself, a coloured-pencil drawing with a distorted, disturbing image of his face.

One of the most prolific serial killers in US history, Samuel Little was convicted of three murders but later confessed to killing 93 people between 1970 and 2005.

A former competitive boxer, Little would knock out his mostly-female victims with punches before strangling them, meaning there were not always obvious signs that the person had been killed. Instead many deaths were incorrectly determined to be overdoses or accidental and were never investigated.

He was finally caught after a routine arrest for a drug-related offence in 2012, when his DNA was matched to the murders of three women in the Los Angeles area in the late 1980s. Sentenced to life, he took up art in prison, when he sketched his own self-portrait, but also drew pictures of many of the women he claims he killed. In 2019, a year before Little died aged 80, the FBI released 15 of the portraits as part of efforts to track down his remaining victims.

Just as some murderers take up art, Richard Dadd was an artist who become a murderer. A promising painter of the Victorian era, Dadd went to the Royal Academy Art Schools and by the age of 25 had won a medal for life drawing and had his illustration published in books.

But in July 1942, and a year after he drew his self-portrait, Dadd went on a trip with a group of fellow artists to the Middle East and underwent a dramatic personality change, becoming delusional and violent, and believing he was under the influence of the Egyptian god Osiris. When he got home, he became convinced his father was the devil in disguise and murdered him with a knife.

Dadd was admitted to Bethlem psychiatric hospital - also known as Bedlam - then Broadmoor hospital, where continued to paint, producing increasingly surreal and fantastical scenes which have become his most famous works.