I worked in the freight business for nearly thirty years (air imports) and once had to tell a client that the urgent shipment of PCBs they were expecting from Japan, that they had brought people in on overtime to install, would not be getting there. Asked why, I had the greatest excuse ever. The plane had crashed into a mountain. Really. There was just silence on the line.
Another time, my boss was dealing with an irate customer who just wouldn't listen. He wanted the price of something dropped I think, long time ago. Our rates were too high or something. So he says to my boss "Oh look, this is ridiculous! I want to talk to someone who can make a decision!"
Grinning, my boss said a phrase I guess he'd been waiting most of his life to say: "You're talking to him. I've made the decision. You're not getting a discount!"
Kind of like that one time I saw on TV where, seriously, these guys called to someone's house in the early morning and the girl leans out the window and says "**** off or I'll call the police!" One of the two guys looks up and no doubt grinning says, "Love, we ARE the police!" Oh my god, it really happened and I saw it!
Then there was the customs officer who was CONVINCED that a shipment of the album "Hotel California" by the Eagles was dodgy, as being in a gatefold sleeve (remember them?) he was sure there should be TWO records in there, but there was only one! Would not be convinced till he phoned the record company. Ah, Customs! That happened before my time.
Or the guy who regularly came on the phone five minutes before we closed on a Friday looking for a quote for "three boxes to go to India", let's say. In the freight business it's all based on dimensions and volumes, so you can't quote without those. Asked for the information he snapped "I haven't time to worry about such things! Just give me the quote!" Idiot.