I work in tech support, and I remember my colleague getting this call.

An elderly lady calls in, trying to install her printer on her PC. She tells my colleague that on her computer screen it says "No printer found", and continues to explain that she's even tried to turn the screen towards the printer and still it says "no printer found"

In my own experience, the stupidest question I ever got, was if the warranty covered the printer being struck by a sledgehammer.. (This guy was actually being serious)

I've got tons of other strange stories as well, but that one is the stupidest one..