I’m going to be doing this with the GOG version of RollerCoaster Tycoon. Enough hard drive space for the install plus about 150MB.And it works with basically anything short of the latest and greatest. I recently noticed that GOG was offering Mac versions of PC-only Black Isle RPGs like Planescape: Torment. My curiosity over what witchcraft was enabling this led me to Wineskin, which now has me running stuff like RollerCoaster Tycoon natively in OS X. If you have fond memories of a PC game of that era and it’s not from Blizzard or id, odds are it didn’t get a Mac release.
What I like most about it, though, is that GOG is up there with Valve in its efforts to make Mac gaming less of a wasteland. When it comes to retro computer games, DOS isn’t too much of a hurdle because the hardware requirements are trivial and apps like Boxer make emulation simple, but the Windows ultra-dominance of the late 90s through late 2000s are a dark spot. They distribute classic PC titles, getting them running on modern operating systems, bundled with extras, and all without DRM.
