I came across a bunch of those recently, which is how I came up with the idea for this, as a parody :)
Internet horror is disappointingly un-creative. I have no idea why the weakest works (sonic.exe, anti-piracy, kill screens) always end up becoming huge trends, or why so few people try to put a significant twist on said trends.
I think it has to do with the age of the target audience? I remember being absolutely terrified and morbidly fascinated by sonic.exe and similar when I was in middle school. What might seem weak/shallow/uncreative to an adult might actually be extremely interesting to someone younger.
whatever.EXE doesn't make my eyes roll as hard as anti-piracy screens because the former at least is working with the premise that the thing has been corrupted by demons and thus isn't supposed to be realistic. Anti-piracy screens often want you to suspend your disbelief that Nickelodeon, Babyfirst TV or anything else aimed toward kids or even free and publicly available like PBS would jumpscare kids with pictures of their mascots bleeding from the eyes because piracy bad.