Re: The older the OS...
The 16-bit PC/GEOS[0] operating system (later just GEOS, then Geoworks Ensemble) ain't nerdcore. Early AOL floppies came with a runtime version of PC/GEOS that could be modified to become HDD bootable. I know a couple of folks who used this as a primary GUI to get computer illiterate folks online.
You want nerdcore? Try DesqView. Ran Win3.x in a window.
[0] Note that the 8-bit software also called GEOS, and from the same company, for the C-64 and Apple ][, is a completely separate code base and mostly incompatible with the later 16-bit code.