Here we’ll go through an example with Wineskin Winery. Sometimes referred to as just “Wineskin” or just “Winery.” The UI is very unfriendly, but does offer a little more configurability than WineBottler, and doesn’t have any donation-begging, nor do you have to suffer through ads in order to download it like you do with WineBottler. WineBottler, which is the easier option to use and has a nicer looking UI, but doesn’t support using different versions of Wine per application, which you might find helpful for older games that can run on Windows 95 but crash on XP.
But you wouldn’t want to run it that way. So there are a couple of different choices for GUI front-ends. Wine itself is a command-line program, installable via MacPorts. Even though it’s technically not an emulator, it fits the theme of this blog. Here’s a walkthrough. Years ago it was called “Windows Emulator,” but later it became Wine Is Not An Emulator. And it’s not – it doesn’t translate instructions, it just translates functions (“system calls”) from Windows to POSIX, which they call a “wrapper” (wraps the Windows software to intercept its Windows API calls). Most games from the Windows-era of PC gaming (as in, pre-modern/pre-Steam-era, or roughly 1995-2005) can be run on Intel Macs (Macs made after ~2006) thanks to a compatibility layer called Wine.