Getting Escape from Monkey Island to run under Residual on a Mac is an exercise in frustration I wish on nobody. Once upon a time, Wine -- the Windows emulator that apparently is not an actual emulator -- was an equal futile experience. These days, times have changed, and after the Rum_Rogers commented that the GOG version of Escape works just fine in Wine, I decided to give it a try. And you know… It worked! For me. Apparently not as much for everyone, but regardless, here are a few steps that might make your life a bit simpler if you want to get Escape running under macOS.
First open Terminal. Most everything here will be done through command line, so get ready for tears and to type in your password at regular intervals.
Type in: ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"
That will install the package manager you need. Next type brew doctor to set everything up.
Type sudo xcodebuild -license -- you may get an error message, and all that means is you’ve already accepted the license.
Next you need XQuartz for window management. Type in: brew cask install xquartz
When ready, run a clean-up for good measure -- brew cleanup -- and then install Wine: brew install wine
Make sure you have the two backup installation files downloaded from GOG…
… in the Downloads folder. Type in cd ~/Downloads to get there in Terminal.
Here, type in wine setup_escape_from_monkey_islandtm_1.1_\(20987\).exe (triple check version number -- it might have changed by the time you read this) and wait. And wait. And wait.
You may get a 32-bit error. That’s fine, and it will happen only one time. Re-run the code above, and it’ll be fine.
And then the regular Windows style installation will start. Set the game up as usual, and boom -- the game should start!
To run it in the future, you’ll find it under ~/.wine/drive_c/GOG\ Games/Escape\ from\ Monkey\ Island/ and you can start it by typing in wine ~/.wine/drive_c/GOG\ Games/Escape\ from\ Monkey\ Island/Monkey.exe
And that’s it. The FSAA was disabled for me, so no guarantees what your result will be, but I’m pretty sure Rum_Rogers will field all your questions in the comments!