Dec 02, 2022 I Nick Redfern

There's a Smile You Never Want to See: It Belongs to the Sinister Grinning Man

Over the years more and more creepy characters have surfaced into our world. They include: the Slenderman, the Black-Eyed Children,  the Shadow People, the Hat Man, the Women in Black and more. Probably the most creepy of all, though, is the Grinning Man. Yes, he has a smile. But, it's not the kind of smile you want to see. Indeed, that grinning thing looks like your average deranged axe-wielder. Or, something even worse. With that said, it's best avoided. Forever. The first case is a fascinating one, because - as you'll see - in this story, the Grinning Man has blended in with the Hat Man. It's a Man in Black-type being that appears in shadowy form; not unlike the infamous Shadow People – to whom the Hat Man is almost certainly related, even if we’re not sure why. On many occasions, however, the Hat Man appears in regular, human form, with a black beard and a black suit, and wearing a long overcoat or a cloak –always black, too. I know this, as I have investigated many such affairs. Most noticeable about this creepy figure is, of course, his hat. Sometimes, it’s a fedora, other times it’s an old style top hat. Occasionally, it’s more like a cowboy hat. But, regardless of the kind of headgear, it’s always present and always black. Many of the encounters occur while the victim is in a distinct altered state – that of sleeping. 

Angie had just such an encounter in Leominster, Massachusetts, on September 6, 1994, as she told me late on the evening of October 8, 2014. Her reason for contacting me was due to the fact that, quite out of the blue, she had suddenly begun to dream of the events of twenty years earlier – and dream of them almost every night for the last couple of weeks. Very much like those people unfortunate enough to be confronted by the somewhat similar Slenderman – the ultimate Internet meme come to life in Tulpa form - Angie was sleeping when the mysterious thing disturbed her sleep by manifesting in her bedroom and staring at her with a menacing grin on its pale, ghoulish face. For a few moments, Angie was unable to move. As she finally broke the spell of paralysis, however, the grinning Hat Man was gone. Now, to another case:

(Nick Redfern) Sinister characters out at night

In 1987, the Maxwell family spent a week vacationing in and around San Francisco, staying with friends in Menlo Park. On their way back home, they traveled along California’s famous Highway 101, which provides a panoramic view of the Pacific Ocean, and for mile upon mile. They chose to drive through the night, when the highway would be at its least busy, thinking that it would be to their benefit to do so. How completely and utterly wrong they were. As fate would destine to have it, after a couple of hours of driving, the family of four spotted a strange light in the sky. It was described as a bright green ball of light, about the size of a beach-ball, one which paced their car and that stayed with them for a couple of miles, at a height of around sixty feet. There was nothing frightening about the encounter. Rather, they were all amazed and excited. It wasn’t long, however, before things got very disturbing. The day after the Maxwell family got home was a Sunday, meaning they had an extra day before returning to work and school. It was while one of the teenaged children was sat on the porch and playing music on an old Walkman that she caught sight of a man on the other side of the road. He was dressed completely in black, aside from a white shirt. He even wore black gloves, on what was a bright, summery day. The girl was particularly disturbed by the fact that the man sported a weird grin and was staring right at her. So unsettled was she that she went back into the home and told her father of what had just happened. He quickly went to the door but – no surprise – the MIB was gone. Now, back to the 1960s.

Jaye P. Paro was a woman who had a number of bizarre, UFO-themed encounters in May 1967, in upstate New York. She was also a host on Babylon, New York’s WBAB station. On one particular day Jaye decided to take a walk. It was barely dawn, and the town in which she lived was still shrouded in shadows. As she walked passed a particularly dark alley, a Woman in Black loomed into view, as if from nowhere, or from some nightmarish realm. Then, out of the blue, came a black Cadillac, the absolute calling card of the MIB. It came to a screeching halt next to the two women, and out of one of the rear doors came an unsettling-looking character. It was a man dressed in a dark grey suit, with an “oriental” appearance, and who sported a disturbing, almost maniacal, grin. The driver seemed almost identical in appearance. The man with the fearsome grin shook Jaye’s hand and said, “I am Apol.” Jaye said that holding Apol’s hand was like holding the hand of a cold corpse. The man gave Jaye a piece of parchment which contained a metallic disc, in terms of size around that of a quarter. Jaye - who later said that throughout this entire, odd experience, she felt light-headed and spaced-out – announced to the WIB and Apol that she was going to mail both items to someone, who happened to be John Keel, although she did not tell the pair who, exactly.  Evidently, both the Woman in Black and the Men in Black were happy, since they again suddenly sported cold, eerie grins. Their black Cadillac immediately returned and whisked the pair away for destinations unknown, but surely no good.

(Nick Redfern) The classic M.I.B. car

Now, let's jump to relatively recent times: on July 19, 2012, Gloria told me – as we drank coffee and ate homemade lemon cake in her living-room – she briefly saw what can only be accurately described as a flying saucer, which hovered over her home as she sat in her backyard, reading a book and with her two dogs for company. In fact, it was the barking of both dogs - which stared intently and rigidly at the sky - that alerted Gloria to the presence of the weird craft. It didn’t stay around for long, however. It was a case of here one second and gone the next second. But that was not all. The next afternoon, that of the 20th, there was a knock at the door. It was a pale-faced, thin woman of about thirty, wearing a long black wig and dressed in a black jacket, a white blouse, and a flowing, black skirt. And then there were the huge sunglasses. And the WIB smelled of dirt – something I have heard before. Gloria felt deeply uncomfortable as, upon opening the door, the Woman in Black proceeded to warn her not to talk about the UFO she had encountered the previous day, due to the claim that “the government is concerned.” Concerned about what was never explained. Clearly, the WIB was not from the government. Or, from any government. According to Gloria, the woman didn’t even look human. “Skeletal” would have been a far better description. After asking what the time was, the Woman in Black turned, grinned weirdly, walked down Gloria’s driveway and vanished. Now, to another angle:

There are multiple comparisons between none other than the Slenderman and Indrid Cold [a creepy, endlessly grinning character who appears in John Keel’s acclaimed 1975 book, The Mothman Prophecies]. Essentially, any creepy shadow-dweller is worthy of comparison. Jack the Ripper? Perhaps. Why not? This begs the question, if indeed the comparison with Cold and MIB is to be considered, are ‘we’ as a modern culture being ‘led’ into these interests? Is there a greater scheme at play?” That question is one we should all be concerned about. Perhaps, the agenda of the Slenderman is so complex and massive that we fail to see the full picture. The smiley-face angle to all of this is notable, as there are more than a few paranormal entities that sport what can only be termed terrifying, maniacal grins. One is Indrid Cold, a sinister Man in Black-type character with an undeniably Dickensian-like name. He roamed around the city of Point Pleasant, West Virginia when, in the late 1960s, the Mothman affair was at its height. Those who encountered this unsettling entity – usually at night - were unable to take their eyes off of his psychotic, serial-killer-like smile. Today, we have a modern day equivalent of Indrid Cold. He is, most appropriately, known as the Grinning Man. Imagine Jack Nicholson’s insane, grinning character of Jack Torrance in Stanley Kubrick’s 1980 movie, The Shining, and toss in a liberal amount of MIB, and you’ll get the picture. 

(Nick Redfern) Mothman!

And, finally...“Christine” grew up in West Texas and was confronted on more than a few occasions that involved the Grinning Man. I leave the story to Christine, herself: "I haven’t told a lot of people about it. When I first saw the person I was about 1 or 2 years old. I have a very long memory. It was like the typical thing that you hear: it was this man who would stand in the doorway of my bedroom. I remember standing up in my crib and holding onto the bars and he wore a fedora and a tan raincoat and black trousers, shiny shoes and black leather gloves. His face wasn’t like someone who had been burned, but he just stood there and would grin. There was nothing friendly about the way he was grinning. It was horrible. Emotionless, didn’t blink. And he came off and on for a few years. Even as I got older and slept in my own bed I would wake up sometimes, like at 3 o’clock in the morning, and that went on. That still happens: all of a sudden I’ll be wide awake at 3 o’clock in the morning, for no apparent reason. But as a kid I’d wake up at 3 o’clock and he’d be there. I didn’t have any frame of reference for it. Of course, my mom didn’t believe me; she just thought I was dreaming."

Christine continued: "But there were all sorts of strange paranormal things that happened throughout my childhood and I wonder if it was all part of the same thing. I even got weird phone calls as a teenager. The phone would ring and it sounded like a little kid speaking in another language; just rapidly talking into the phone. I thought at the time it was some little kid got on a payphone and started dialing numbers from another country. But, when I read The Mothman Prophecies, I went: Holy shit! This was the same thing. What kind of validated that this person was real was that when I was twelve, a friend and I were out riding our bikes about 9.30 at night in the summer – it was a small town in west Texas. And we stopped and were looking in the doors of the Baptist church, as they had just put in new carpets. A big Saturday night! But, we both turned at the same time to look behind us and this man appeared like right on the edge of the street light and started walking towards us, and he was wearing the exact same outfit: the fedora and the tan overcoat and black pants. But, this time, his whole head and hands were bandaged. We didn’t speak; we just took off like a shot, around the corner, to her house. We didn’t know what to make of it, but I thought it was probably that same person that I used to see. I’ve never saw him again."

There's still more to come: "When I got into my early twenties, I was living in Dallas and I met a girl; we got to talking about paranormal stuff and she lived in Lufkin, in east Texas. She said that she and her sister shared a room and that sometimes she would wake up and there would be this man in her room. She said he wore a hat and a long coat. He reminded her of the McDonald’s “Hamburglar” and he would just stand there grinning at her. One night, she woke up and he was looking at her, but he was petting her sister’s head while she slept. And, then, a few years later, another friend of mine who had grown up in New York, she had seen a similar man and that would stand in her room. I thought, okay that’s great; I am absolutely not nuts. I had lights that would turn off and on. My stuff got moved around all the time. I still have my things get moved around. I had a poster of Marilyn Monroe jump off my wall. It was like 6 o’clock, I think I was sixteen, and it just flew off the wall and into middle of the floor. I grew up in a really religious family: southern Baptist; so that was all something of the Devil, although I don’t believe that now."

(Nick Redfern) Women in Black: a clear connection

It gets very creepy: "There was another visible entity that used to show up. It was black sort of shapeless, but had these enormous eyes, kind of like the quintessential way we depict aliens. The great big eyes, but they were silvery with no pupil. They had a reflective quality. Again, it would be 3 o’clock in the morning and I would feel my bed jolt. And I would look down and see those eyes, right over the edge of my bed, and the black shapelessness around it. I turned on the light once I got my courage up. I thought: if I don’t move it’s going to kill me, and if I do move it’s going to kill me. Again, I was sixteen or seventeen. I screamed for my mom. I just told her I had a nightmare. But then I saw it again; one morning I was getting ready to go to school and I turned toward the shower and I could see the eyes looking between the hooks on the shower curtain. The final time this thing ever appeared I didn’t see it. I had a friend sleeping over, a senior in high-school. She had never been to my house and I had never told her about any of this kind of stuff. She was very religious; didn’t really believe in any of this or would have said it was the Devil. We’re up the next morning, and she was helping me make my bed and I said: “It was a lot of fun; you should come back over.” And she looked at me and said: “I’m sorry, I’m never gonna come back here.” 

Christine's final words on this issue: "I said: 'What did I do?' She said: 'You didn’t do anything. How do you not remember?' I said: 'I really don’t know what you’re talking about; you’ll have to tell me.' She said she woke up suddenly during the night and she thought that she couldn’t see. Then, when her eyes adjusted, there was a face so close to hers that she couldn’t see anything else. I asked her what it looked like and she said the same thing: these big eyes and just black. She said she screamed so loud she figured she woke the whole neighborhood. All I did, according to her, was lift up and sit up on my elbow and look at her and said: 'Are you okay?' And she said she was and went back to sleep. My mom didn’t hear it either. And, surely enough, she never came back to my house. I did have a person who would actually call me and talk to me while I was in high-school.

"It may have just been some nut, but he seemed to know everywhere that I went. I took dance classes in Abilene and I had friends that lived there as well. And this person would call late at night and ask: 'How was your dance class?' He knew my every move, which was odd. They wouldn’t tell me who they were. They knew a week’s worth of my activities. I might have decided to see a friend and not had those plans prior. So, no-one would know where I was going, but this person knew where I had been. The last time I saw him was in a dream when I was thirteen and it was like a lucid dream, and I was in a store, looking at a rack of magazines. And I turned and looked to my left and there he is, and he’s got a magazine in his hand and staring right at me and grinning. And in the dream I put my magazine down and I walked right past him and told him: “Don’t ever come here again.” And he never did. That was the last time I saw him, physically or in a dream. I just decided, right there, in my dream I’m not having this anymore."

Nick Redfern

Nick Redfern works full time as a writer, lecturer, and journalist. He writes about a wide range of unsolved mysteries, including Bigfoot, UFOs, the Loch Ness Monster, alien encounters, and government conspiracies. Nick has written 41 books, writes for Mysterious Universe and has appeared on numerous television shows on the The History Channel, National Geographic Channel and SyFy Channel.

Join MU Plus+ and get exclusive shows and extensions & much more! Subscribe Today!