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When we were kids, my best friend and I would call random numbers from the phone book and pose as phone co. technicians. We'd say that there was some work being done on the lines in the area and that the customer should not answer the phone for the next 15 minutes or the person on the other end could receive an electrical shock.

About five minutes later, we'd call back the same number and when the person answered, we'd let out an agonizing scream and hang up. Usually we'd call the number again about a minute later and see if they answered again. About 1/2 the time, they'd let it ring.

Ah, the fun times before answering machines and caller ID. :)

A bunch of us were hanging out and this guy used to work at a fast food place down the road. He called up to this place and asked to speak to the manager. Once the manager got on the phone, he told her that he was so and so from such and such power company and that they had noticed a change in the power being sent to that fast food place and he asked if they had the lights on, and she said yes, and he said that it seemed to be a great deal of power and perhaps she should go check a major appliance, such as the refrigerator. She goes and checks and gets back on the phone and says "sir?" and he says "yes, ma'am. Is you refrigerator running?" and she actually said "yes" in complete innocence. So then he goes on with the "then you better go catch it!" and slams the phone down. It was great. She was so dumb.

When I'm in a cranky mood, I like to play pranks on the bozo telemarketers. Or would that be a pranky mood? Try to engage in a long, circuitous conversation. Make up some story about how I'm running from the law or that I'm a homeless person or whatever comes to mind at the moment. Or if the person on the other end of the line is a chick with a nice-sounding voice, be flirty with her and ask random questions about her or tell her I'll buy whatever she's selling me if she'll go out with me. Every now and then, you'll get somebody who will stay on the line and talk and believe all the BS I'm making up. If they're gonna invade my privacy by making my phone ring inside my home, the gloves are coming off and I won't hold back. haha

Years ago my buddies and I used to frequent the building next door's cafeteria, which was on the top floor.
Took note of the lift phone's number and called it later, with the conversation something like this
Us "Hi, its the lift technician here, are you in the such and such a lift in that building?"

Sucker "Yes"

Us "Well you really shouldn't be, because we are supposed to be replacing a badly frayed support cable"

Sucker (Maddly pushing the stop button to get out) "UUUUGGGHHH"