What's a an old and creepy, odd, disturbing, etc,. piece of software/shareware that you're aware of?

Not sure if this is an appropriate sub to ask this, but here it goes:

I had just watched this video, which features a lot of recent disturbing games from some off-putting one-man developers (like Demonphobia), with the oldest game on the whole list only being from 1990.

I am curious, however, if there have been other creepy, weird, disturbing, etc,. pieces of old software and shareware, especially those made before the internet became more common (like around the mid 90's).

I know the only pre-internet way to share software was either things like BBS or sharing via floppies or cassettes... Or you would just buy it. I'm curious what creepy, disturbing, off-putting, etc,. stuff was ever shared or purchased in certain circles between the 70's and early 90's.

The biggest stuff I could think of are crappy porn games, especially shareware... Which honestly aren't even that surprising in my eyes.

The story/software could either be personal (like "Yeah, a crazy friend of mine put a threatening image on some of the school's Apple II's. He's now locked away in an asylum.") or it could be from someone you don't personally know, a group, a weird company, etc,.