We had a VP who refused to type in a password. If his machine rebooted, he had to call someone to come to type in his password. He was constantly sending us Info Week articles on alternatives to passwords like fingerprint readers. We fixed the problem by canceling his subscription to Info Week.
Our new head of Computer Security was also the head of the Diversity Initiative. He sent out a newsletter every month that was infected with a Word virus. Every month, we would have to clean machines that had accessed the document. He refused to believe he had a virus because, after all, he was the head of the Computer Security.
We were working on a project at work, and one of the people on my team sent me this, which I suspect you will appreciate!