Games from over 20 years ago that work well with Wine on other platforms:

- Morrowind doesn't start after the launcher.

- Manhunt runs at 5 FPS. Five!

- Oddworld: Abe's Odyssey doesn't start

- Deus Ex is too slow to be playable

- Jet Set Radio doesn't start

- Half-Life Blue Shift works well

For Morrowind you should use OpenMW https://openmw.org/downloads/

The rule of thumb is generally that for Windows games pre-2008ish, Parallels is a better choice, since they tend to rely on weird corners of Windows compatibility and 32-bit performance in Wine is still not always great. DXVK + MoltenVK is generally the best choice for anything post-2000s, pre-DX11, and GPT/D3DM is generally the best choice for anything DX11/DX12.

Are any of those DirectX 12? The GPTK only supports DirectX 12, anything else won't get much of an advantage.

When was the last time you tried? It's gotten a lot better since I first tried it (probably like 15 years ago)

All of those today, about an hour ago. As I said, they work fine with Wine on Linux but not with Wine/Whisky on the Mac.

That’s my experience too. It looks like some modern games that are 64 bit and use DX12 and thus game porting toolkit‘s dx2metal work quite okay, but 32 bit DirectX<11 games run particularly awfully.

And I’m running what the community has dubbed the best way, crossover with cxpatcher.