It didn't work particularly well.

Wine used to involve a lot of black magic and trading configs to get things to work.

With the right incantations, and some luck and a few DLL replacements, you could make things mostly work.

3-D rendering was a shit show earlier on. You just didn’t even try. DirectX was everywhere and unusable. It was probably a slow march, but it felt like a sudden boom when 3D started working and suddenly 2/3 of your games/apps would work natively with a smaller config/spell.

Nothing like the lengthy spell castings of early wine. I summon thee brood wars!

If you weren’t a software engineer, you probably weren’t getting it to work for anything.

Not sure what to say, yes, it was more difficult. I remember getting games from humble bundles that were Windows only, got those bundles for the Linux games it had. Some of them I got to work easily, others were just not running or had performance issues.

For a time it had a commercial fork for gaming called WineX. It mostly handled DirectX and incompatible DRM. Still not nearly as reliable as Proton.

There were also a ton of helper programs like today. The general cycle was:

1. Wine on its own works well.
2. The more programs you add the worse it works.
3. A hip new helper comes along with program specific tweaks.
4. The tweaks start being over engineered.
5. The tweaks stop working in more and more cases as the Windows programs get updated.
6. return to 1.

I honestly thought that Lutris would have reached step 6 by now but so far it seems to be holding on.

I think I first used it around 2004ish. It was barely useful with basic applications without doing work, you could use it to have fairly decent support once you figured out the process. I think I was able to get an SNES emulator and a barely stable N64 emulator to run.

It was basically a best last option if you needed to run a windows program and couldn't/wouldn't do a dual boot.

So yeah, they definitely improved things.

I basically only used it via crossover office way back when when there was a time I had to use Lotus Notes for email.