Chilling Artworks By Serial Killers That Offer An Insight Into Their Minds

Image: via UpShout

Some serial killers like to boast, while others take their dark secrets to their graves. Either way, figuring out what makes their warped minds work is sometimes beyond even the best psychologists. But the paintings and cartoons produced by some of America’s most infamous killers can offer a chilling glimpse into the inner workings of their psyches…

Image: Via Perth Now / Via Murderpedia

10. Alfred Gaynor

From April 1995 to February 1998, Alfred Gaynor cold-bloodedly killed a total of nine women, all in Springfield, Massachusetts, and all in horrific circumstances. The former handyman was finally apprehended, though, and he is currently serving eight life sentences, giving him plenty of time to work on his macabre art.

Image: via Pinterest/Private Island Party

Paintings such as Murder Beach, seen above, give a disturbing insight into Gaynor’s mind. It is perhaps easy to see the twisted imagination that saw him leave his victims’ bodies in grotesque poses, often for their loved ones to find, at work here.

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Image: San Quentin State Prison

9. Richard Ramirez

As the “Night Stalker,” Richard Ramirez terrified Los Angeles in the mid-1980s. Indeed, during his sick spree, he showed “cruelty, callousness and viciousness beyond any human understanding,” according to the judge who sentenced him to 13 death sentences. His crimes? Shooting, raping and bludgeoning dozens of victims.

Image: via Pinterest/Grant Willing

The stark black-and-white pictures produced by Ramirez – who spent 23 years on death row – are testament to his identification as a Satanist. In fact, during his trial, the serial killer shouted “Hail Satan!” and he never expressed any remorse. Ultimately, Ramirez died from an illness in jail.

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Image: via Pinterest/Sheri Keeney

8. Charles Ng

Only Charles Ng himself knows how many people he killed, but the authorities put the figure at between 11 and 25. What is known, however, is that, in a cabin in the Sierra Nevada foothills, he and his partner-in-crime, Leonard Lake, tortured their victims before killing them.

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Image: via Pinterest/Private Island Party

Ng is on death row at San Quentin prison in California, where he passes the days painting. Ironically for such an infamous criminal, his works are largely bright, vibrant affairs, featuring mermaids, fish and even flowers – a marked contrast to the darkness of his crimes.

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Image: via Murderpedia

7. Keith Hunter Jesperson

In the 1990s Keith Hunter Jesperson murdered, at minimum, eight women, and he was called the “Happy Face Killer” because he taunted detectives with letters signed off with smiley faces. In one of his particularly nasty crimes, he strapped a victim’s body to the underside of his truck and drove it along in an effort to destroy her face and fingerprints.

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Image: via Pinterest/Private Island Party

Jesperson – who claims to have taken the lives of as many as 160 people – is serving a life sentence in California, and clearly the attention-seeking that gave him his nickname hasn’t dampened. The killer is a prolific painter, though his pieces are more the work of a twisted mind than an artistic genius.

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6. Henry Lee Lucas

Once captured, Henry Lee Lucas claimed to have killed hundreds of people, though a conviction for 11 murders was enough to ensure that he would die behind bars in 2001. The Virginia native’s spree between 1960 and 1983 saw him often choosing his victims among those who, like himself, lived on the edges of society.

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Image: via Pinterest/Private Island Party

Before he died of heart failure in prison, Lucas painted a number of works, some far more disturbing than others. One of the more tranquil ones – a picture of his family home – was included in a 1993 exhibition of serial killer art.

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Image: Jacksonville Police Department

5. Ottis Elwood Toole

A one-time lover of fellow serial killer Henry Lee Lucas, Ottis Toole was a drifter who murdered at least six people before he was apprehended in 1983. Nobody knows for sure just how depraved Toole’s life of crime really was, though he confessed to rape and even cannibalism as well as arson and causing death by strangulation.

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On appeal, Toole’s death sentence was commuted to one of life imprisonment, and he used his time inside to paint, often producing grotesque portraits far more likely to be of interest to a psychologist than an art critic. Toole perished in prison in 1996, aged 49.

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Image: SHERIFF’S DEPARTMENT/AFP/Getty Images

4. John Edward Robinson

For many, twisted John Edward Robinson was the first serial killer of the internet age, making contact with his victims through online chat rooms in the 1990s. Active from 1984 until his arrest in 1999, the Illinois native and family man killed at least eight people, though investigators believe he was responsible for many more deaths.

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Image: via Private Island Party

Robinson is awaiting a lethal injection in Kansas and uses his cartoons to rail against the authorities. In his own words, “Through art, those on America’s death rows can contribute to both society and what should be a meaningful dialogue about capital punishment.”

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Image: via Kirsten Lee

3. John Wayne Gacy

Even Stephen King couldn’t make up a killer as twisted as John Wayne Gacy. Dubbed the “Killer Clown,” he killed and sexually abused at least 33 teenage boys between 1972 and 1978. Chillingly, he entertained children at parties while in costume as his creepy alter ego, “Pogo the Clown.”

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Image: via Miami New Times

The psychopath was executed by means of lethal injection in 1994, but not before he had created dozens of paintings, a lot of them featuring Pogo the Clown. Soon after Gacy’s death, a bunch of these works were auctioned off, with a number of them being burned in a communal bonfire attended by relatives of his victims.

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Image: via Dearly Departed Tours Hollywood

2. Arthur Shawcross

In 1987, in what must be one of the most infamous errors in American judicial history, Arthur Shawcross was given early parole after the manslaughter of two minors. Within months, he was killing again, and overall the so-called Genesee River Killer claimed the lives of 14 people, all of them young women and most of them prostitutes.

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Image: via So Bad So Good

Shawcross was apprehended in 1990 and died in prison in 2008. While incarcerated, the killer took up art. But where his crimes were extraordinarily brutal, his paintings were dull, tranquil watercolors; did he yearn for an escape from his crazed thoughts?

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Image: via Murderpedia

1. Danny Rolling

One of America’s most notorious killers, Danny Rolling found infamy when he murdered five students in Gainesville, Florida. That spree earned him the nickname the Gainesville Ripper, and he also admitted to three more slayings. In any event, he was executed by means of lethal injection in 2006, having never shown any sign of remorse.

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Image: via News Beast

While awaiting execution on death row in Florida, Rolling penned poems, composed songs and drew pictures. His black and white pictures are creepy, to say the least, often featuring naked women or, in some cases, the grim reaper. Infamously, his works are collectors’ items among fans of “Murderabilia.”

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