I guess I'm gonna take another shot of these threads because some weren't shitposted as much as last year, and before. I'm gonna go ahead and get started anyway,
So, we all know that the "Jeff the Killer" image predates before the Creepypasta, and that it is a well photoshop-edit (well duh) of a girl who allegedly "committed suicide" named "Katy Robinson" due to bullying. A screencap of it is provided, but there is no evidence that such a thread exists, despite being that old.
We all know that rumor is real, right? You're wrong. The image of Heather White dates EARLIER than 2008 and got posted on a Christian parody maymay site around 2005.
A FB user got in touch with her, and she said that she isn't the girl behind the photoshop, nor she has anything to do with the rumor. Someone thought it would be funny to make her into some sort of morbid joke as a meme.
Other than that, there is this early theory going around indicating that pics related come from a fugly autistic girl on Stickam. Despite how ugly she looked towards some, she got impersonated by someone screencapping a still of her smiling (either from a live chat or profile page) and shitposted it towards the /b/ forums (whether 4chan or 2chan, we don't really know for sure, but a lot say 4chan might be the case). The OP pretended to be the girl, asking "Am I pretty?" in the thread. Soon enough, her image got progressively shopped by others, and eventually, the OP pretended to complain about said shops and immediately left. Nobody can really confirm this as this was all back around 2005 when 4chan got ahold of camwhores and underage maymays.
The only thing we can figure out is how long it took for that OP to crosspost the girl's image, where it actually got shopped from, who the girl in the photo is all along, and what her face actually looked like before it got shopped.
If there are any archives of the thread that exist around that timeframe, including all shops, let alone the unedited pic, let me know.