No, it has happened to me. More than once. I've been the dumb young cashier that snooty old dads pull this move on. Then they'd try to give me a patronizing math lesson, loudly, on the spot. Sometimes, their wives would at least grant me the dignity of looking embarrassed to be with them.
My own father has come home / over bitching about these exact same types of interactions too, over the years. Use your ******* credit card, if it bothers you so much DAD.
The thing is, I actually don't think most cashiers freeze up when they're given weird change because they are dumb. It's just unexpected, and they're often not sure why someone is giving them an odd configuration. Plus, there's usually a big line they're expected to keep moving. I think this kind of transaction should be alluded to in training, so that new workers will recognize it.