The closest I've ever come to a prank call was when I was in college. I worked at Radio Shack, and one of the local old timers came in to buy a cable for his computer. This was about 1980 or so, and I was at first a bit surprised that this old timer had a computer hooked up to his radio for whatever reason. The only reason I could think of at the time involved contesting. I thought maybe he was using the computer to generate CW, which I thought was pretty progressive for this old timer. So I innocently asked him, "so, you must be a contester!" Up until that point, he had seemed friendly enough, but he looked at me with a look of rage and said, "hell no!" I quickly dropped the subject. Some time later, I happened to hear him on 2 meter FM when I was with some friends. I related the story, and during a lull in the conversation between him and another old timer, one of us jumped on frequency and called, as fast as humanly possible, "CQ Contest." The other one jumped in and in an equally frantic voice, shouted "59." Of course, we ID'ed, and there had been such a long lull in his QSO that we didn't interfere. He came back to the other old timer and just muttered, "Oh, my God."
Back in the 11m Daze there were DX clubs that shot skip on legit channels om SSB that identified with "Prince Albert" numbers. Back then, by "Gentilemans agreement" sideband was only operated on Ch 16, and from channels 34-40....
I asked on 7185 about Eustachian Tubes and the ex-CBer said at his station they were all 3-500s. He asked me, “what you running at you station?”
Breaker 16 Breaker 16 for the Fish Monster Skipper, you need your radio fixed What is wrong with my radio good buddy? Your CB is broken and transmitting on 156.8 MHz FM. You need that fixed right now!
Another one was 1B3GT Popular prank calls from kids in the 30s, 40s and 50s, pretty much harmless: The phone rings at a small town grocery store. The voice on the other end asks, "Do you keep Prince Albert in cans?" When the clerk answers yes, the caller warns, "you better let him out before he smothers to death". Another, "Is your clock running?" "Yes." "You better go catch it, then." Later, prank calls, usually from teen-agers, became more nefarious. Bomb threat to school the morning before a big exam, for example. The advent of caller ID pretty much brought prank calls by kids to an end.