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16 Chilling Facts About Hitman Glennon “The Dentist” Engleman

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16 Chilling Facts About Hitman Glennon “The Dentist” Engleman

To quote Little Shop of Horrors, “You’ll be a dentist. You have a talent for causing things pain. Son, be a dentist. People will pay you to be inhumane.” Nothing could be closer to the truth for Dr. Glennon Engleman who truly was a horror movie come to life. He is no longer with us and assumed to be in a very hot environment now so feel safe visiting the dentist with confidence. But if you were a patient of Dr. Engleman’s in the 60s to 80s and didn’t feel like paying your dentistry bill, especially if you were female, you were seriously in danger of losing your life to the bad doctor in a particularly gruesome fashion. While only seven of his victims have been actually verified, it’s widely believed by the people who knew him (including his would-be victims) as well as prosecutors and detectives working his case that his murder count was exceptionally higher. Refusing to give closure and relief to the families of his victims, Dr. Engleman took the details of his victims and other crimes down with him. If you’ve always feared a trip to the dentist, welcome to your worst nightmare.

16. His Thrill Was Planning Different Ways To Kill

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You know that saying, “find something you love to do and you’ll never work a day in your life?” Dr. Engleman found that to be true as he enjoyed every aspect of planning different ways to kill his victims. He started with bludgeoning. He then moved on to shooting (he had hunting experience, we’ll get to that later) and after this, he began to get creative in a very twisted way. One of Dr. Engleman’s victims had the horrible misfortune to die in a car bomb that he planted. Another one of his victims met a gruesome fate after being thrown down a well chased by lit sticks of dynamite. The creepy aspect (aside from the whole murdering part) is that Dr. Engleman is a dentist, a profession that many people fear is for those who enjoy inflicting pain. While not true for the general population of dentists, this definitely seemed to be the case for Dr. Engleman.

15. Patriotic Passion For This Prolific Murderer

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What does an evil dentist have to do with military benefits and fate? Well, had it not been for his time and service to the U.S. Army Air Corps, Dr. Engleman might have been Mr. Engleman. How would this have affected his killings? Well, chances are high that he still would have been a sociopathic murderer but the lives of his female patients would have been spared. He attended and earned his degree from Washington University of St. Louis’ school of dentistry and was able to attend college under the G.I. bill. Exact dates of Dr. Engleman’s time in the service isn’t known but he graduated from Washington University in 1954 so it’s possible that he served during World War II. Dr. Engleman joins other notable serial killers such as Timothy McVeigh, Jeffrey Dahmer, Son of Sam killer David Berkowitz, and Green River murderer Gary Ridgway as famous murderers who bring much shame to Americans everywhere and the entire nation by having served in the U.S. military.

14. Hollywood Inspiration

This 1996 cheesy horror movie was based on Dr. Engleman though the real dentist’s motives were far more nefarious. The fictional Dr. Feinstone (portrayed by Corbin Bernsen) kills because *SPOILER ALERT* he catches his wife cheating on him, and other reasonable motives according to the horror movie world. In real life, Dr. Engleman had truly sick reasonings (not that any reason is good for these horrible actions) that we’ll explore a little later on this list. The Dentist was followed two years later by The Dentist 2: Brace Yourself. Gotta love that subtitle humor. Before The Dentist hit the big screen, Beyond Suspicion also billed as Appointment For A Killing was a TV movie that first aired in 1993 starring Corbin Bernsen, Markie Post and Kelsey Grammer — all based on everyone’s least favorite dentist. Apparently, Hollywood loves a good depraved dentist story! There’s nothing like preying on the general fear of visiting the dentist to make you jump out of your seat.

13. On The Hunt For Bigger Prey

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Dr. Engleman first attempted to satiate his thirst for taking innocent lives by killing animals. He tried his hand at hunting and bought all of the proper equipment and went on several hunting trips, as reported by family and friends. Reportedly, he kept some parts of the animals as trophies. He even tried hunting large exotic animals. While he started off enjoying his new murderous hobby, it wasn’t what he was looking for and did not satisfy his appetite for murder. To take his hobby to another level, he turned to the ultimate hunt: human lives. Now this seemed to satisfy him though he did keep upping the ante in the way he killed as noted in #15. Dr. Engleman has something else in common with David Berkowitz and Jeffrey Dahmer as serial killers who used to torture and kill animals. Other notable animal and human killers (aka severely twisted individuals) include Ted Bundy and Albert Desalvo.

12. He Had A Surprising Way With The Ladies… And Used It To Kill

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Judging from Dr. Engleman’s photo, you may be surprised to learn that he was something like a walking Axe body spray commercial but for the women in his life, it seems to be true. First up is Ruth. Though their marriage ended after just three years, the pair decided to keep on good terms — very good terms. You see, Ruth still received money from her ex (on their own terms, not alimony payments) and they had created some sort of friends with benefits situation plus she got free dental care whenever she wanted from him. Win-win. Shortly after Ruth remarried, her young husband wound up with a mysterious gunshot. Lucky Ruth received a nice life insurance payout however. Next on his list of lovely accomplices ladies, he seduced his very own dental assistant. 24-year-old Carmen was talked into marrying a man for the sole purpose of Dr. Engleman shooting him and splitting up the life insurance money. Then there was Barbara who allowed her lover, Dr. Engleman to shoot her new groom and his wealthy parents. Keep in mind, these are just the ladies that are known to have been involved with his murder schemes!

11. Money Motivated

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While it seems that Dr. Engleman truly enjoyed killing for the “fun” of it, he also had monetary compensation on his mind when he plotted and schemed the demise of his victims. As noted above, life insurance was a major motivation for him. There was some talk about possible troubles with the I.R.S. but by all accounts, the dentist was making good money in his practice. Perhaps the thrill of earning a sweet little payout was just a part of a sick game for him. Here’s a rundown of some of the money he made taking lives. An exact amount is not known for his take in the $64,000 payout that his first wife, Ruth received for the death of her husband but it was probably pretty sizeable. Next, he received $16,000 from a $25,000 payout from the widow of a man he killed and used the money for his drag racing business. His dental assistant agreed to pay him $10,000 from the $75,000 she received when her boss murdered her husband in cold blood. He also received a nice chunk from a $190,000 policy from the lady he was having an affair with after he killed her in-laws and husband. Murderous and greedy? There’s not much to like about this guy.

10. Just A Kid From St. Louis

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Born in 1927 and raised in St. Louis by his railroad worker father and mother, alongside three siblings, sister Melody and two brothers, in a modest home. Dr. Engleman had a normal start to life for such a not-normal human being. He was described as an average student in school, earning slightly less than average grades at times. But he managed to succeed in finding a good-paying career after school and found it in his heart to give back to the community by treating some of the city’s poorest patients on the house. This earned him some brownie points around the neighborhood and once he got his own practice, he was known as one of the more decent and respectable members of society. He was a war veteran who seemed to truly care about the people in his neighborhood. That is, until people closely connected to him started turning up dead — in truly horrific ways, no less.

9. A Life In Exchange For A Drag Racing Business (Which Failed)

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One of the dentist’s business ventures was the fine art of drag racing. He even managed to convince (with his Bond-like sexual prowess, no doubt) his former girlfriend to toss some of the blood money a.k.a. life insurance payout ($16,000) she received into the drag racing business which Dr. Engleman believed was sure to be a huge success. It wasn’t. A business fail in exchange for a man’s life doesn’t seem very fair. Not to mention that this was Eric Frey, who suffered a truly horrific death at the hands of the dentist and who believed up until his death that he was to be part of the drag racing business. Unfortunately, he was the Dr. Engleman victim who wound up in an exploding well. Can you imagine how terrified Eric was to see those lit sticks of dynamite crashing into the well after him? Apparently, Dr. Engleman and Mrs. Frey thought that Eric’s life in exchange for money and the chance to kill was more than fair.

8. Many Matrimonies

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We already went over the fact that Dr. Engleman was a ladies’ man. But he followed through with some of those ladies all the way to the altar. All in all, he was married three times, first to Edna “Ruth” Ball in 1953, the little charmer that allowed her ex to shoot her new husband and split the payout with him. Apparently, she had a bit of a wild reputation in St. Louis for causing major scenes in local bars. The police questioned the heck out of her for the shooting death of her second husband before giving up after they were given a hard time by the community for “verbally attacking” her. It seems that Dr. Engleman and Ruth’s relationship was something of the “one that got away” for both of them as they stayed in contact, sometimes intimately, throughout the years. Then he married Eda G. Vanhest just three years later in 1956. Not much is known of their marriage. While the dentist was a ruthless killer, he was a ruth-full lover. His third and last trip down the altar was to a woman who was also named Ruth (née Jolley) in 1967.

7. Multiple Life Sentences In Prison

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For his brutal murders, Dr. Engleman had already been sentenced to double life terms while new charges for other murders were still being investigated. It was as if he killed so much that the district attorney could barely keep up! In fact, while the case of his lover, Barbara’s husband, Ronald Gusewelle and his parents, Arthur and Veronica Gusewelle’s 1977 murders were being investigated, he was busy serving two back to back life sentences. At their collective trial, he decided ‘what the hey’, he was already in jail and had nothing else to lose so he pleaded guilty to the hit of the family. As a result, Dr. Engleman’s sentence became a triple life term. After this, he was sentenced to another thirty years which was useless at this point, unless Dr. Engleman was a vampire and capable of living 330 extra years, but served to give a sense of justice to the family of Sophie Barrera, a dental laboratory owner who the greedy dentist owed a big outstanding bill to. Rather than simply pay his debt, his decided placing a car bomb in her vehicle would be a smarter financial move.

6. Hollywood Heartthrob Casting Delight

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Actor Corbin Bernsen (you might know him from USA’s Psych) was a bit of a hottie back in the day and in 1996 when The Dentist premiered, he was still definitely in his prime. Rumor has it that when Dr. Engleman saw who Hollywood had cast as his movie counterpart, his was quite pleased with the choice. Of course, Dr. Engleman was not sitting in a comfy movie theater chair while enjoying plenty of popcorn with flavored toppings on the side but locked up in the stony lonesome where he rightfully deserved to be. Police reporter Bill Bryan said that Dr. Engleman had a cocky and almost macho way about him. It was clear that he thought very highly of himself and was probably pleased to see such a handsome and successful actor playing his slightly fictionalized self. But then again, perhaps he was so cocky that he thought Corbin Bernsen was not up to his level.

5. Diagnosis: Sociopath

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This probably comes as no surprise but just like Dr. Engleman’s multiple life sentences, he was diagnosed as a sociopath a few times over, too. From the time of his capture to his death in prison, he showed zero remorse for the suffering that he put his victims and their families through, further torturing them by refusing to release important information that would help the families with closure but at the same time, seemed to relish the details of the horrific crimes. Police investigators who interviewed Dr. Engleman reported that he was highly intelligent with an IQ near 140. He liked talking about parapsychology and signs of the Zodiac to one reporter. The Zodiac Killer struck in the 1960s and 1970s and gained huge media attention. This all happened while the dentist was free and out committing murders of his own. You have to wonder if he was really interested in signs of the Zodiac or was perhaps just playing to the media to gain extra attention.

4. The Dentist Was A Daddy!

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Not much is known about Dr. Engleman’s son, David. He was born to Ruth Jolley, the third (and final) wife of the cavity-fighting hitman. But then again, if your father was famous for all the wrong reasons such as being a sociopath hitman, you probably wouldn’t seek out attention either, right? What is known is that David was born after his parents’ marriage in 1967 so that means that he was born amidst his father’s murders. David would have been born before the murder of James Bullock, his first wife’s new husband and the murder of Eric Frey in the well. After Dr. Engleman’s only child was born, he continued his killings. Bear in mind that Dr. Engleman refused to give a full confession so there could have been many other killings in between his multiple marriages and the birth of his child that we don’t know about. By all accounts, he was a loving husband and father but I suspect only his family knows the real truth of that statement.

3. Dr. Engleman’s Three Murderous Decades (That We Know Of) And The Takedown That Put Him Away

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Dr. Engleman’s killing spree lasted for thirty years from 1958 to 1980. Had he not been caught, who knows how many more women he would have cajoled and talked into setting up heinous crimes with him? A chilling aspect of his case is that his kills seemed to get only more brazen, more bold, and more brutal as the years went by. Finally (and luckily for his potential victims), while police were investigating the horrific car bombing that claimed laboratory owner Sophie Barrera’s life, they talked to wife #3, Ruth who broke down and told police that she was in fear for her safety. Apparently, she had been hearing things that led her to believe that her husband was ready to make her his newest victim. Fearful, she agreed to wear a wire and get her dentist husband to confess on tape with police listening in. No one knows how many more decades would have been filled with his victims had she not bravely chosen to cooperate because Dr. Engleman showed no signs of stopping or slowing down.

2. Lasting Legend Of Dr. Engleman?

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Besides The Dentist movies in the 90s, it would seem that the legend of Dr. Engleman’s creepy killings live on today. FX’s miniseries Fargo has a character that is too Engleman-esque to just be a coincidence. Billy Bob Thornton plays Lorne Malvo, a hitman and conman who gains the trust of a dentist only to kill him then briefly assumes his identity. While Dr. Engleman was an actual dentist, the hitman/dentist connection plus Thornton’s look is all very Engleman — do you see the resemblance in the photo above? There have been several other cases of evil dentist characters on the tube from The Simpsons to the movie Marathon Man and let’s not forget Little Shop of Horrors. Certainly, an evil dentist makes for a surefire scary/creepy character so Dr. Engleman isn’t necessarily responsible for all of the character creations that resemble his life but it’s a definite possibility. It wouldn’t be the first time writers of TV and movies pulled composite characters based on real life events and after all, truth is stranger (and scarier!) than fiction.

1. Death By Diabetes

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For a man who played God, taking lives as he saw it, the one life that he left to natural causes was his own. He died behind bars in his Jefferson City prison cell due to complications of diabetes on March 3, 1999 while he had barely made a dent into his 330 year prison sentence. He was seventy-one years old on the day of his death. His female (“lovestruck” according to some officials that worked the case) accomplices got off with much lighter sentences compared to his, one receiving twenty years. He left the world with a quote of, “It takes a certain kind of person to be able to kill another human being.” It’s a quote that was perhaps carefully designed to leave the interpretation up to each individual but knowing what we know of Dr. Engleman, it’s unlikely that he meant it in a remorseful way and rather as a way of paying himself an impressive compliment.

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