One time I got our computer stuck in a loop of trying to continuously start WarCraft II. I had its shortcut in Windows configured to automatically reboot the system into MS-DOS mode with modified autoexec.bat and config.sys files (this was Win95, I think. You could tell the system to reboot when launching an app and specify the settings to use in those files) to free up the necessary memory. On exiting the game, it was then supposed to reboot the system using the normal autoexec and config files.
Unfortunately, somehow the computer got stuck running the modified versions and kept starting the game instead...
Suffice to say, once I got it working again my mom wouldn't let me use the Windows launcher anymore....