There was an official port of both Jedi Academy and Jedi Outcast, available on the Mac App Store, Steam, GOG.com, etc. Those are still available, however they will not work on any version of macOS after 10.14 Mojave. Version 10.15 Catalina and beyond (Big Sur, Monterey) all drop 32bit support, and Aspyr (who ported them previously and more recently to consoles) stated they have no plans to update the games to work on modern macOS. Only a couple mods have updated their Mac versions as well to have native support.
If you plan to only play base Jedi Academy multiplayer, follow this video tutorial. It explains how to install EternalJK, which is currently the best way to play base multiplayer. You can follow that same tutorial but for Jedi Outcast, you'll want JK2MV.
For Jedi Academy singleplayer (and multiplayer if you don't want EternalJK), you can use OpenJK.
These options are very limited in terms of mods and honestly just makes things complicated. I highly just recommend using the options below, which will ensure you have access to any mod you want by using the Windows versions.
That leaves us with running the games in a more unconventional and non-native method called Wineskin, or more importantly, a Wineskin app called Porting Kit that makes it easy to run older games like these.
It's worth noting that Porting Kit works only with GOG.com versions of these games, due to the non-disc and non-DRM install process. However, I also tried it with the non-disc installer that was provided in the Limited Run USB drives, and they work just as well. Using these installers will be the easiest way to do this.
At the end of this tutorial I will explain how you could also install the Steam version or any other version to use with OpenJK or EternalJK, since all you need are the assets for mods like that.
Installing Porting Kit
Porting Kit makes this process easy. Start by going to their website below and downloading the app and installing it. The DMG or ZIP file won't matter, whichever you prefer.
Luckily it will run you through most steps needed for all this. The app opens on the News page, but you'll want to click over to Library. They have a pretty extensive library of games if you ever want to install any other old ones. Search for "jedi" to show both of these games and choose one to install. All steps in this tutorial apply to both games.
Choose your game and click install.
It should open and give you 3 options like this:
It's pretty straightforward. Click Download installer now to be taken to GOG.com to buy and download the offline backup installers. Once you have it downloaded, click Sure, which will then run through an installer. Click through to the end, where it will ask you to locate the installer file and let you select it from your Downloads folder. If you have the Limited Run installer instead, simple click Sure and select that installer. This app doesn't distinguish what you are installing, which we will use to our advantage if you want to use a non-GOG copy.
Let it run and do it's thing. It may take a minute or so with a couple pop-up windows and eventually show the installer for the actual game itself. Run through that as you normally would. Everything from here on out should look like Windows, basically.
Be sure to not run the game in that window once it completes. It should pop up with a window asking you which executable to run, like so:
Be sure to choose either jk2mp, jk2mp, or if you're installing Jedi Academy, your options will be jasp or jamp. Pick the one that you plan to play the most, it's up to you. If you want shortcuts to both, I will cover that below.
The game should show up in your Porting Kit library now. The first thing you'll notice is that it is quite small with a black background. You'll want to immediately go into SETUP and change the resolution to something bigger. I also recommend turning off full screen, but that's up to you. You will need to restart the game for the black background to go away if you turn off fullscreen. It's now installed and ready to go!
Adding a shortcut to MP or SP
If you want a shortcut to both modes, you can easily do that by going into Porting Kit, click the game, then click More, go to Advanced Tools, then click Add Shortcut to EXE. Name the shortcut whatever you want, such as Jedi Outcast MP, or JKA MP, or SP, whatever applies.
Then browse to the .exe that you didn't choose during the install. So if you chose jk2sp.exe last time, you'll want to find jk2mp.exe. If you're unfamiliar with Windows, it should be in ProgramFiles/LucasArts/Jedi Academy/GameData, or something very simliar. GOG might list it under ProgramFiles/GOG/JediAcademy or something like that. Poke around and you should find it.
That should make a new shortcut in your app for that executable and you can now launch both. Repeat this process for any mod launchers you have as well. More on that below.
You saw above that the file structure is exactly like in Windows, so installing mods should be self explanatory to mod veterans: put PK3's in the base folder. You can find your base folder very easily by going to that MORE menu like above and clicking Open C drive and navigating through the folders from there. Drag and drop PK3's into the base folder from there.
Obviously follow the instructions that each mod provides for installation. Any client-side mod like JA+ that don't have their own installer should go into GameData by default, but just make sure to read their own instructions, as they are all Windows based instructions that will apply to you now, rather than Mac instructions.
If you're installing a major mod that has it's own installer like Movie Battles II, do the same steps as above but choose Install Patch/Mod and select the downloaded installer for it. It should then run through the install process as if it is Windows.
If you're unsure which type the mod is, go by the file that you downloaded. If the file is one .exe, it needs to be installed. If it's a PK3 or a folder with a bunch of pk3's and other files, it should go right into GameData. If it's one PK3 file, it goes into base. Again, just follow the instructions provided by the mod itself. Comment here if you need help.
Installing Steam, MAS, or disc version
You should only be reading this section if you don't already have the game on GOG.com or the Limited Run USB drive. If you do, skip the hassle, that way is much smoother. You're reading this is if you already have the game on Steam, the Mac App Store, or even the old disc version (either PC or Mac disc should work).
The workaround here is to run a random installer when it asks for one, so that it creates all the necessary files and configurations and then you can copy your assets and OpenJK into the C drive folder. The random installer we will choose is the official SDK for Jedi Academy. Download it below.
Unzip by double clicking it. You should see the .exe file for it. Run through all the steps above but use this EXE instead of the GOG or LR ones. It will show an error at the end about not able to open a .htm file. Click okay to ignore it.
It will ask which exe to run at launch. It won't matter which one you choose here since it will be changed later, so I just chose ModView.
Follow the instructions above to open the C drive and have that ready. I'm breaking down each version first and the common steps under that, but these are assuming you don't already have the games downloaded on your computer already. If you do, skip past this.
As of now, it is still possible to download incompatible Mac games on Steam. So go download the game via Steam as you normally would. Then when it's done, go to the Library page for the game and go to Browse local files.
It'll show an app. Right click the app and go to Show Package Contents, then go to Contents. You should see the base folder there with all the assets.
Mac App Store
Go to the App Store app, and click your name in the bottom left. It should show all of your previous app purchases. Find Jedi Academy or Outcast in that list and download it. If you can't find it, you either aren't signed in to the account you purchased it with
Go to your Applications folder, find the game.
Right click the app and click Show Package Contents, then go to Contents. You should see the base folder there with all the assets.
The disc versions should be easy to do, as long as you still have a disc drive to put them in. External disc drives are extremely cheap these days, so I recommend looking on Amazon if you have a device without one (chances are, this is you). Once you open up the disc's folder, you'll be able to find the base folder there.
If you have a PC disc, you should still be able to run it and get to those folders no problem on Mac. Again, you just need the base folder.
Now go back to the window that you had open with the C drive for the app. You'll need to make a new folder for the game. I recommend creating a folder structure similar to how the installers do it, just for the sake of simplicity, however you can potentially make whatever folders you want, as long as base is inside another folder.
So in the C drive folder, go into Program Files and create a folder called LucasArts, and inside that folder create a folder called Jedi Academy, and inside that folder create a folder called GameData.
Go back to your Steam/MAS/disc game folder, drag or copy/paste that base folder into this new GameData folder. So now you should have it like so:
Now that you have the assets, you'll need OpenJK or whatever client mod you prefer. For SP I recommend OpenJK (download below has both JKA and JK2 support), and for MP I recommend EternalJK for Academy and JK2MV for Outcast.
Put whatever items related to your version into the GameData folder.
Now is the tricky part. You'll need to go into the MORE button again, go to Advanced tools, go down to Launch Wineskin app. Go to Advanced. Go to Browse and browse to the relative .exe file. So if you got OpenJK for Outcast, choose GameData/openjo_sp.x86.exe.
Next, go to the Tools tab, and then Config Utility. Go to Graphics tab, and check the box next to "Automatically capture the mouse" and click Okay.
Close that window and now click PLAY to launch the game. It will launch, and you'll notice a weird issue with the mouse cursor. Bring up the console (the tilde ~ key on your keyboard) and type in_mouse 2
Restart the game and it hopefully will be working fine.
Please let me know in the comments if you have any issues. This guide probably seems very complicated but it's not! It only gets complicated if you want to use the Steam version, but hopefully this explains it well.