Evil software idea: Cancel Roulette
When doing some task on Windows and clicking the ESCape key, I often see dialogs like this:

and today was thinking: some software asks if I want to save, other software asks if I want to cancel, but a software developer who hated her customers could have some real fun with this by varying the messages at random within the same program:

requiring the user to really pay attention each time. There's lots of room for imagination here.
How fun would that be? :-)