When I did phone support for Compaq laptops back in the late 90's I had plenty of odd and interesting calls.
Three that I recall were...
1: Man calls asking to fix his POS compaq laptop, these were only consumer level laptops, not business level. He was very irate as soon as the call started and after taking call after call for 1.5 years straight I basically went out of my way to be a dick or help as little as possible when people were dicks. If they were nice I'd go out of my way to help.
Anyway his drive died, he had no back ups and said his whole entire business was on there. I apologized for this and told him there are data recover services/companies out there and gave him the number to one we gave out but told him they're very expensive and there's not guarantee they'll recover anything.
He demanded my name, he demanded my supervisors name, he demanded my managers name, which I gave him. He said he'd "sue us all!!" (with lots of anger in is voice mind you).
Then he actually started crying, full on sobbing on the phone. I asked him if there was anything I could help him with while he was sobbing and he "no" he just sound so broken, I *almost* felt bad for him.
2: I was helping a young lady out with some various issue and there was a bit of time waiting on it to boot into safe mode and she got to talking about how many different technologies were out there now days (mind you this was in 1997) and got onto the topic of "cybering". I was thinking I knew what she meant but wanted to be sure
so asked her to tell me more, and she said "you know, cyber sex!, it's like phone sex but on the internet" Needless to say she was very flirtatious but I couldn't help but picture some heffer on the other end of the line.
3: An older guy called in asking for help with his battery and within the fist 20 seconds of him talking I knew exactly what the issue was and how to fix it so I just said "I'm familiar with this issue, please click on start...,settings..., control panel then double click on system" I was actually making a point to go slower with this guys cause I could tell he'd have a hard time keeping up just from everything before. So he yells at me "stop treating me like I'm a god damn idiot!!!" and I responded "I'm sorry if you feel like an idiot sir, I was merely going through the standard steps to resolve your issue"
He didn't like me essentially calling him an idiot and said he didn't want to talk to me anymore, I told him he was free to hang up and call back if that's how he felt. He took the suggestion and hung up.
Ah it was fun screwing with people sometimes.
My buddy that worked there with me for some damn reason went into a Indian accent mode (he was white) when on a call, the whole call he did the full on accent and when he hung up I said "WTF was that all about?" he said he didn't mean to but when the guy on the other end spoke he had a thick Indian accent and when he spoke it just came out like that with the first few words so he didn't want the guy thinking he was mocking him so he just ran with it.
I worked for a sheriff department for a large county back in '99 doing Y2k udpates to some 2,000 computers and had to update or replace computers any and everywhere they had them, including high security jails, undercover operations, forensics labs, etc.
That was just awesome more than anything, I really like that job.
One part of it that stands out though is I was updating a computer of some jail guard in his office and as part of my procedures for computers that were just being upgraded and not replaced, I'd clear their internet cache, back then by just going into the dir and deleting the files. Well I went into this guys folder and went and highlighted all the files and before I deleted them a few file names caught my eye. I don't recall now specifically what it said but it was kiddie porn pics and sites in his history. I reported it to my boss asking what to do he said "just delete it and doing say anything" so I did. I was 19 then and in hindsight, I feel like I probably should have mad this guy burn, that's just fucked up shit.
Another experience is the forensics lab, it was very high security and I had to be escorted down there since I didn't have clearance to get into some of the areas I needed to. But one time they get me in there and then go "well time for lunch" and head off. I'm in a room that has guns, all sorts of drugs and a freaking pallet of weed in the same room with me! Of course I didn't touch shit but that was kind of crazy.
In the main jail for the county they had the maximum security prisoners on the top floor of the building and they didn't have bars for them, they had thick bullet proof looking glass instead so they couldn't reach through the bars and grab anyone when they walked by. Well every time I'd walk through there some of them would start pounding on the glass as hard as they can making a thunderous sound and yell things at me like "you sure look pretty white boy!!!" and things of that nature trying to get me to look. The guards always just said don't look, don't even acknowledge you hear them.