The most troublesome one at the moment is Populous: The Beginning. Specifically, the DirectX version.

The game has two EXE files:

There is a software-rendered version which works fine on Win8, PopTB.EXE.

The one I want to work is D3DPopTB.exe, which crashes every time with a page fault of some kind. I'm pretty sure the crash is due to it using DirectX 7, which just doesn't work on Win8. I seem to recall the page fault is in the D3D libraries somewhere.

I've been reading through forums on Populous Reincarnated and GOG.com, and everyone's solution there seems to be to just run the software-rendered version. Which is not what I want. Though it's what I'm doing for now because I have no other choice.

Neither VirtualBox nor VMWare can run this thing well in Direct3D mode. I think I got one of them to sorta kinda do it at one point, after a ton of tweaking and secret tricks and installing special drivers and editing the VM config files, but it was a slideshow when it ran, even while slamming my CPU/Video to 100%. I tried a ton of workarounds and config tweaks based on all the weird tweaks and things found in message boards and FAQs and howtows on the net, and none of them got it running satisfactorily in the VMs.

I had originally been wanting to do the same kinda thing with Homeworld, but then they came out with Homeworld: Remastered and I just bought that, and it's pretty good.

Most of my TRULY older games were in DOS and so run great under DOSBox with a bit of tweaking.