At my last job 3/4 of the staff could not understand the fax or copier at all, and kept coming to me (the administrator) to say it was broken, but as soon as I went over to the machine and looked sternly at it it would spit out whatever they had tried to copy/fax.

I would die laughing if some character actually got a computer error message like my co-workers used to report to me, things like "It just won't print," or "It's broken."

There's also the outside auditor who comes in with an inch-thick stack of paperwork to do the annual review and insists on asking each and every question verbatim despite the fact that you've already provided them with the entire form filled out by email, and it's all the same as last year. Including "do you have a wheelchair accessible office?" when they just walked into the office and saw for themselves.

Oh, and the paper-hoarder. Someone who hates paperwork but whose job requires a lot of documentation, and thus always has a ton of paper sitting (or hiding?) around their office waiting to be filled out, some of it from 1997. And they get super-defensive if anyone asks when the paperwork will be finished.