Look at this one for example - my mind is blown: https://blog.decryption.net.au/images/macpaint/lesson3d.png
How do you even do that? Zoomed out it looks like a nearly photorealistic street scene, zoomed in I just see seemingly meaningless patterns of black and white. Magic. Unbelievable.
This image in particular made me wonder if there was some type of tracing aid involved. Maybe the dutch-looking street reminded me of Vermeer's method. I wonder what input device they were using? I was using a pretty nice input surface for doing CAD work sometime around 1990-93 on a PC, and we had occasion to lay transparencies on top and trace on them. I don't know if Macs 5 years before that had this type of peripheral. And anyway, there were certainly some special artists I knew of back then who could do this with a mouse and enough time.
They could have been cleaning up a scan of a photo, ThunderScan came out real early in the Mac's life.
Scanned drawing + painting over it with dither patterns is an option too.
There's a few - including that one - that look like they're photos pulled through a transformation code. I'm probably wrong though - dithering seems to be incredibly difficult to get right, see e.g. https://forums.tigsource.com/index.php?topic=40832.msg136374...