Oh Dear God. (Probably Cthulhu.)
@foone I’m always in for a Brautigan reference.
(It’s so sad how far away we are from the techno-pastoral paradise he imagined.)
@wavejumper3 They're mostly screenshots of the original OSes running in emulators. I used Visual Basic 6, Visual Basic.NET, Word Dialog Editor (from Office 4, I think?), and MUSH, the tool for controlling Agent characters like Clippy.
The DOS EDIT one is a lot of careful paint.net manipulation of pixels, combining a few screenshots while respecting the underlying text grid