Because it's a somewhat lengthy pasta, I'm just going to link you through to the original Jeff the Killer post on the Creepypasta Wiki rather than attempt to rehost it here. For anyone wanting to read it, the story is a available in its entirety there.
The JtK pasta on the wiki probably isn't the original. There's more than one version, and the story appears to have started with a YouTube video in October of 2008. Still, they all have one thing in common: that picture with the terrifying eyes that bore into your soul.
The story as posted on the creepypasta wiki is the one most commonly associated with the memetic picture, despite its lack of precedence, which is the reason why I've chosen it for the review here. It's also the perfect story to make a point about creepypasta and what separates it from more traditional horror fiction, so it seems fitting for an early post on this blog.
If you read the Creepypasta wiki's Jeff the Killer pasta, you'll notice something pretty quickly. Quite frankly, for a story so popular that it's spawned numerous spin-offs, hundreds of pieces of fan art, and a character sometimes compared with Slenderman and The Rake, it's not very good. That isn't to say that it's terrible, but there are serious grammar issues, and the dialogue can range from under-affected to "why did the cops take horse tranquilizers?":
Jeff grabs the kid’s wrists and breaks it..
We all look up to see him holding a knife. (story is not in the first person)
"Well kid, looks like a year in Juvy…”
Basically, one of the most popular creepypastas on the Internet sounds like it was written on the spur of the moment and never edited. I strongly suspect that's what actually happened, with the author deciding that the picture deserved a better backstory than the one given in the original YouTube video, and crafting something blending the minimal details of the video with one of the Joker's maybe-true stories about how he got his scars from The Dark Knight.
There's a unique situation in which a work like this can become more popular than it would in the world pre-Internet. First, it was self-published without cost. That's important. A low bar to entry means that a story not considered publishable in print can be made available to thousands of people, and some of them are probably going to like it. Second, it had the potential to reach a huge number of people through the endorsement of a handful. That, too, is important, since it means that a story like this can do its own advertising.
There is a third aspect to why Jeff the Killer is so popular, of course, and as I've said already, it's that picture.
How this story got associated with that image is probably a result of luck, since it isn't original, but the fact of the matter is that even popular stories rarely becomes outright memes without something that sets them apart. In this case, that's the haunting piece of multimedia associated with it. I knew about the picture long before I knew that there was a name attached to it. There's another, shorter version of the JtK pasta that omits the backstory, and probably led to the imposition of "Go to Sleep" on the original image:
The picture itself isn't a photoshop. It's actually a screencap from the movie Inland Empire. I've never seen Inland Empire, and I have no particular desire to do so, although I probably wouldn't turn it down if I had the chance. I have no idea what the context of the horrifying .jpg is in the film, and given that it's a movie by David Lynch, I seriously doubt that knowing the context would help very much.
It's hard to say which one came first, the original JtK post on YouTube, or the first posting of the image on the Internet. Obviously it would be pretty much impossible to find Inland Empire screencaps from more than 5 years ago, given how swamped they are in a sea of "GO TO SLEEP".
The more important thing about the picture isn't whether the terrifying image was circulating as a scares shot before or after the creepypasta. It's the fact that it is horrifying for some reason we can't quite identify. It's terrifying on a deep, biological level, because it lives somewhere far in the recesses of the uncanny valley. It has no nose, its mouth is too big, its eyes are too sunken. It's the perfect creepypasta monster, because creepypasta, in its purest form, is terrifying on the same level.
Creepypasta, by which I'm referring to the original short blasts of anonymous microfiction rather than the longer stories now commonly well-attributed to a specific author, comes out of nowhere. The most you can know about its source is that a person with a particular IP address decided to post it at some point after either coming up with it or hearing it somewhere else. There's no name attached, no description of their motivation. Ripping away context is horrifying in its own little way.
Beyond that, the topic of the creepypasta is usually frightening because something it describes is a real threat. Obviously Jeff doesn't exist, but look at that picture. What does he really look like? Are you more afraid that he'll stab you, or that he'll give you whatever disease took away his nose, made his skin pale, and caused his eyes to sink so deep into his skull that they look like they're staring out at you from the bottom of a pit? Jeff looks like a person suffering from an unspecified but destructive necrotic skin disease.
The fear of diseases that appear to bleach the skin and cause decay while the victim is still alive goes back thousands of years, to some of the earliest human records of pestilence. From Leviticus 13:
4 If the bright spot be white in the skin of his flesh, and in sight be not deeper than the skin, and the hair thereof be not turned white; then the priest shall shut up him that hath the plague seven days:
5 And the priest shall look on him the seventh day: and, behold, if the plague in his sight be at a stay, and the plague spread not in the skin; then the priest shall shut him up seven days more:
6 And the priest shall look on him again the seventh day: and, behold, if the plague be somewhat dark, and the plague spread not in the skin, the priest shall pronounce him clean: it is but a scab: and he shall wash his clothes, and be clean.
7 But if the scab spread much abroad in the skin, after that he hath been seen of the priest for his cleansing, he shall be seen of the priest again.
Despite the fact that Jeff is more frightening because of his appearance of disease than anything else, you also can't deny that his mouth makes him look somewhat predatory. That broad grin, expressing so many teeth, makes him look like a hyena, and you know what probably tasted really good to hyenas? Those stupid primates that really liked walking around on two legs for some reason.
So, apparently, Jeff is a diseased were-hyena. I'm not going to disagree with my natural fears on this one. I think that diseased were-hyenas are terrifying, too. Come to think of it, maybe a diseased were-hyena would make an even more horrifying creepypasta than the one that we actually have.
Most creepypastas, because they're short and don't require a lot of detail, can prey on those natural fears better than longer form fiction. These are things that we fear for rational reasons, but it's not that hard to just take the elements that cause the most horror and give them a fictional treatment.
Or, you know, maybe there's another reason why we're afraid of things like this:
Many classic horror icons, such as Geger’s xenomorphs, Silent Hill’s
Pyramid Head, and other
disturbing creatures, share common
characteristics. Pale skin, dark, sunken eyes, elongated faces,
sharp
teeth, and the like. These images inspire horror and revulsion in many,
and with good
reason. The characteristics shared by these faces are
imprinted in the human mind.
Many things frighten humans instinctively. The fear is natural,
and does not need to be reinforced in order to terrify. The fears are
species-wide, stemming from dark times in the past when lightning could
mean the burning of your tree home, thunder could be the approaching
gallops of a stampede, predators could hide in darkness, and heights
could make poor footing lethal.
The question you have to ask yourself is this:
What happened, deep in the hidden eras before history began, that
could effect the entire human race so evenly as to give the entire
species a deep, instinctual, and lasting fear of pale beings with dark,
sunken eyes, razor sharp teeth, and elongated faces?
… Just be careful out there.