From disturbing sketches of their fantasies and kills, to demonic visages and eek-worthy babies, a lot of strange art has come from the minds of jailed serial killers. Some of it, as you would expect, is amateur to childish, while some demonstrates real artistic talent. Given our collective fascination with the morbid and eerie, it's no surprise that these images from killers who made art are as compelling as they are strange and disturbing.
John Wayne Gacy
Is there anything creepier than a creepy clown? John Wayne Gacy penned a number of such pieces during his time behind bars, many of which features Pogo the Clown. This is even more disturbing when one considers that Gacy was also known as The Killer Clown, as he was a member of a volunteer group that dressed up as clowns for fundraising and volunteer events. Gacy's clown identity was as "Pogo" or "Patches" the Clown. Creepy as it is, of course, there's no evidence that Gacy was ever in his clown getup when he murdered any of the 33 boys and young men for which he was eventually caught and convicted.
Keith Hunter Jesperson
Keith Hunter Jesperson killed a confirmed eight women in the United States and Canada, though he claims to have killed as many as 185. His flair for the dramatic, which can be seen in his drawings as well as his life, led him to be in regular contact with the media after initially not receiving enough attention for his crimes. He earned the nickname the "Happy Face Killer" by signing his letters with a smiley face, including his first "letter," which was, in fact, written on the wall of a bathroom stall in a truck stop, in which he confessed to the murder of Taunja Bennett.
Bobby Ray Gilbert
Bobby Ray Gilbert, unlike prolific killers like Ted Bundy or John Wayne Gacy, has only a couple of alleged murders in his past. One, for which he is serving three life sentences, was a murder committed during a robbery. The second, the murder of a fellow inmate. And the final potential murder, more interestingly, is for a murder he confessed to while in prison: the killing of Troy Wicker. The strange thing about this case is that another man, Tommy Arthur, was executed just a few years ago for this murder. However, he maintained his innocence until the end, and Bobby Ray Gilbert maintains his guilt. Given the disturbing, if talented, nature of his artwork, it's not too hard to believe either way.
Richard Ramirez made a number of disturbing sketches behind bars, many while on death row for 13 murders and 11 sexual assaults, among other crimes of burglary and attempted murder. His callous behavior and complete lack of remorse led him to be sentenced to death in all 13 counts of murder—however, he died of B-cell lymphoma in prison before his sentence could be carried out. His art was clearly influenced Satanism, of which he was a self-proclaimed follower. Though other serial killers like Henry Lee Lucas certainly surpassed him in number of murders, Richard Ramirez is considered by far one of the most disturbing killers in our history, given his complete inability to feel or demonstrate any kind of compassion or remorse.
Although Danny Rolling's body count is lower than many other serial killers, the crimes for which he was arrested were committed in a shocking spree, during which he killed five students in four days. Later, he admitted to murdering a total of eight people, and sexually assaulting many of them. Between his arrest and sentencing in 1994 and his execution in 2006, the "Gainesville Ripper" produced a number of works of art, which generally demonstrated both a deeply disturbed mind, as well as a moderate, but genuine talent for drawing.
Henry Lee Lucas
Perhaps the most disturbing artwork to come to us from behind the bars is that of Henry Lee Lucas. Fittingly, Henry Lee Lucas was also one of the world's most prolific serial killers, confessing to as many as 3,000 murders, and convicted of 11 murders. Of course, the real number is believed to be somewhere more in the realm of 350. He was ultimately sentenced to life in prison, a time which he spent making deeply disturbing art, among other things. After his arrest in 1983, he spent nearly two decades in prison before his death in 2001.
Henry Lee Lucas was a drifter and a traveler, murdering across state lines for years. For some of this time, he was accompanied by Ottis Toole, a mentally challenged man with an IQ of 75 and fairly severe epilepsy. Toole, like Lucas, confessed to hundreds of crimes. However, also like Lucas, he was only ever convicted of a small portion—in his case, six murders. Despite his violent tendencies, which were believed to be at least partially due to an abusive and violent upbringing, Toole often demonstrated childish behavior and understanding, which further manifests itself in his somewhat juvenile, though often demonic, drawings.
Despite the seemingly wholesome content of Gaynor's art, the man himself was responsible for a number of seriously heinous crimes. He was guilty of the murder of at least seven women. Some of these women he posthumously posed in gruesome and grotesque ways, to be later found by family or friends, including young children. To further contradict the messages of much of his artwork, like that seen above, many of his victims were introduced to him through their mutual quest for illicit drugs, a habit he used to find, rape, and murder his victims.
Dennis Rader, also known as the "BTK Killer," murdered 10 people—including a family with two young children—between the 1970s and 1990s. His nicknamed, the BTK Killer, is an acronym for "Blind, Torture, Kill", which was his M.O. He lived and killed in Kansas, where he is currently serving a sentence of 75 years without parole for these crimes. His art is uniformly disturbing, often mixing violent and pornographic elements, such as nude women being hanged or bound, as well as disturbing messages and writing. Overall, not the kind of thing you want hanging on your wall.
Ed Gein is one of the world's most influential serial killers. His disturbing habit of making furniture out of murdered or exhumed bodies has made its way into a number of pop culture icons, including Buffalo Bill in the film Silence of the Lambs, Norman Bates in Alfred Hitchcock's Psycho, and even some of the decor in original The Texas Chainsaw Massacre. After his murders and exhumations, he also created some surprisingly gentle-looking works of art, including this almost dainty drawing. Of course, if you include his furniture, he was making art long before he joined the ranks of killers who made art behind bars.
David Berkowitz, or the Son of Sam, became one of the world's most famous serial killers after successful escaping authorities for a long time, while sending regular letters to mock the media and police for their failures. He earned his name by claiming that he killed on the orders of a demon in the form of a dog, owned by his neighbor, Sam. However, he later admitted this was untrue, and stood trial as mentally competent. Despite this, his artwork does indicate a deeply disturbed mind. He has since also claimed his murders were part of his role in a Satanic cult, but this claim too has since been questioned.