Okay, I'm not sure this will fix the issue, but try this build:
http://vectorpoem.com/playscii/playscii_win32-9.17.1_20210419.zip
It's using the latest version of Python, PyInstaller, etc; I want to make sure I'm using the latest before I file a bug with the PyInstaller project.
If it gives you an error and the error is any different, let me know.
You might also try running playscii.exe from the Windows command line, and see if any meaningful error text results.
Thanks for your patience!