Anything around DirectX 10 and older has issues with Windows, these days.
One more popular example is Grid 2, another is Morrowind. Both crash on launch, unless you tweak a lot of things, and even then it won't always succeed.
Need for Speed II: SE is "platinum" on Wine, and pretty much unable to be run at all on Windows 11.
Unfortunately the modding community is split because OpenMW only cares about supporting the original game and not the script extender ecosystem that modders have built around it.
Windows used to be half operating system, half preconfigured compatibility tweaks for all kinds of applications. That's how it kept its backwards compatibility.
One more popular example is Grid 2, another is Morrowind. Both crash on launch, unless you tweak a lot of things, and even then it won't always succeed.
Need for Speed II: SE is "platinum" on Wine, and pretty much unable to be run at all on Windows 11.