SpyParty player coocoofroggy/steam did some helpful investigation on how to get the game (both the spyparty.com and steam versions) working on modern versions of macOS.

Here is the website purchase version of the HOWTO:

I have Spy Party working on MacOS Big Sur, super user friendly.

It takes 4 steps and less than 10 minutes!

1. Simply download PlayOnMac (https://www.playonmac.com/en/) and the Spy Party setup exe (for windows! not Mac) from the website (https://secure.spyparty.com/beta/download-latest.php).

2. Open PlayOnMac > Install a program > Install a non listed program

- "Install a program in a new virtual drive"

- Name it anything (I did "spyparty")

- Leave everything unchecked

- 32 bit installation

- Gecko? I clicked yes, I don't think it matters

- Browse, select your Spy Party installer .exe

3. Finish the installation wizard as normal

3b. When prompted, add the spyparty.exe shortcut to play easily, name it whatever you want

4. Click your spy party shortcut from PlayOnMac to run the game! Runs as smooth as on Windows.

Bonus

If your mouse doesn't move the camera/sniper

5a. Open the game, right click the game's icon in the dock > options > show in finder

5b. Open system prefs > security and privacy > privacy > accessibility

5c. Drag in the application that you found in 5a into the list in 5b

Bonus 2

If you want to be able to open Spy Party with one click:

6a. Right click the Spy Party clover on your desktop and click show package contents

6b. Contents > MacOS > right click "playonmac" and choose 'make alias'

6c. Put the alias on your desktop or dock or wherever you want to launch it from

Bonus 3

Find replays on Mac (since ctrl-O opens the virtual explorer)

7a. Open finder, do Cmd Shift G

7b. In the window that opens, paste this:

~/Library/PlayOnMac/wineprefix/[DRIVE NAME FROM STEP 2]/drive_c/users/crossover/Local Settings/Application Data/SpyParty/replays

replacing [DRIVE NAME FROM STEP 2] with your drive name

7c. Hit enter to get to the replays folder!

And here is the Steam macOS HOWTO:

Play Spy Party on MacOS Big Sur Steam Version

Give yourself 30 minutes of free time.

1. Download PlayOnMac (https://www.playonmac.com/en/).

2. Open PlayOnMac > Install a program > Search for Steam. Click Install at the bottom right

- Keep clicking Next + Install

- I believe you need Gecko so click yes if it asks.

- Once done, Steam should launch (or you can launch manually from PlayOnMac home screen)

3. Let Steam update

3a. If it says Steam crashed after install, just close the crash window

4. Close Steam (right click the steam icon in your dock and click 'Quit')

5. Click steam on the PlayOnMac home screen, click configure

- Go the second tab labeled "Wine"

- Click "Configure Wine"

- Go to the Libraries tab (second from the bottom)

- Click *dwrite (disabled) and click Edit on the right

- Click "Native then Builtin" and click Ok

- Do the same for *gameoverlayrenderer (disabled)

- Click Ok at the bottom to save and exit wine configuration

6. Run Steam again, and log into your account that owns Spy Party

7. (The Store tab looks awful. Ignore that) Go to the Library tab and install Spy party.

8. Launch Spy Party through Steam once done!

Bonus

If your mouse doesn't move the camera/sniper

9a. Open the game, right click the game's icon in the dock > options > show in finder

9b. Open system prefs > security and privacy > privacy > accessibility

9c. Drag in the application that you found in 9a into the list in 9b

Bonus 2

If you want to be able to open Spy Party with one click:

Spent an hour figuring this out. Need more time

Bonus 3

Find replays on Mac (since ctrl-O opens the virtual explorer)

7a. Open finder, do Cmd Shift G

7b. In the window that opens, paste this:

~/Library/PlayOnMac/wineprefix/Steam/drive_c/users/crossover/Local Settings/Application Data/SpyParty/replays

7c. Hit enter. You're now in the replays folder!

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