Private Investigators don't usually have the glamorous jobs that they are portrayed to have in TV and film.
Most of the time, P.I.s are investigating the affairs of someone's personal life: are they cheating on their spouse, are they hiding money from somebody they owe it to, etc.
But sometimes PIs do get really interesting cases.
Here were some of those answers.
Keeping The Stalkers At Bay
my s/o had a stalker who would send him flowers, we would come out to our front garden to find notes or gifts (it was a secured area), and once got a glassine envelope left at the front door with what appeared to be cocaine in it (i guess the reasoning for this was my s/o is a musician and we all know how messed up THEY are and all the drugs they do). Then crazy letters started getting sent to neighbors about how i was a murderer, a thief, a prostitute.
this went on for a couple of months so we hired a guy who came highly recommended by our attorney. BOOM. caught 'em. it turned out to be a married woman who had a bad crush on my husband. We didn't press charges but we had the attorney scared the living crap out of her. and that was the end of it. I'm sure this wasn't the most difficult case he ever had but he was so quick with the result - mind blowing that our life was put back right so quickly.
I've hired multiple of them for my job. I'm a work comp adjuster so putting surveillance on people that you think may be faking it or not sticking within their restrictions is not unheard of. Not used nearly as much as you'd think and you rarely if ever get the reports you'd imagine. The best ones you'd find would be people claiming they have terrible back injuries and unable to do anything and then find them out doing manual yard labor or whatever. But the most interesting one was a guy who had an alleged shoulder injury. Every time he was about to be placed at MMI (Maximum Medical Improvement) his alleged pain would increase substantially.
The way he injured the shoulder was questionable as he claimed it was from lifting a 5# box. We put surveillance on him but never found anything. Then randomly one day the department of insurance got an anonymous letter with pictures of this guy claiming he was doing home renovations and had pictures to prove it all. It looked like the work of a PI but it was all anonymous and got so much more than what the professional did. Our guess was it was a pissed off co-worker of the claimants because this same claimant had a prior claim with an altercation with another co-worker.
Cartwheels And Spiderwebs
I'm a private fire investigator.
I found a hogtied elmo covered in white paint in the basement of a vacant building in a terrible part of town. I'll find the pictures in a minute.
Just so much porn from everyone. Little old ladies, dudes living around, middle age moms. Everyone has so much porn.
I once had a guy admit to setting his house on fire just because I was nice to him. I mean it was super obvious and he knew I'd figured it out, but I just talked to him about football and all that and right before I left he just flat out admitted to it.
I had a fish tank shatter next to a power strip starting a fire and put the fire out. Family couldn't figure out why it was so hot in their house since the fire started in the basement and they never saw it.
Had a guy tell me that the church across the street would gather in the street and pray his house burned down. Turns out the tenant who was staying there's boyfriend actually did the burning and not Jesus as one church member claimed.
One girl offered to watch her roommate's dog for the weekend then got annoyed by its' barking so set it on fire. She is the only truly evil person I've ever seen.
I had a gun pulled on me on a fire scene that made me sh!t diamonds. Guy was complaining outside the house that some girl had told the police he had set it while I was standing inside the house unable to move for fear of letting them know I was there. I waited for a car to drive by to provide some noise cover then hauled it out the front door. He came around the front of the house pistol drawn and aimed it at my truck as I finally got it to go. Called the police and they told me to just not go back. Which is suuuuuuper helpful.
Being in dark rooms tends to make your imagination do some crazy things. Especially with fatalities.
I'm sure there are more I can't think of.
Edit: Elmo photos
Woman I know had to get one as part of her divorce. The husband had been cheating but in order to get infidelity as part of the divorce hearing there needed to be a witness that saw him go to the other woman's house after 10pm and there for at least an hour (or something like that).
She said the strangest thing was that the PI was like a 50 year old woman that you would never guess was a PI.
Not a PI, but the subject of a PI, thanks to u/Horsefrend for this comment as a reminder:
I know an investigator that dresses like a stereotypical PI with the long coat and fedora. His job is to investigate and verify that kids actually live in the county of the school that they are attending.
I didn't realize this was a thing, but for most of my grade school/middle school tenure I lived in a different district than what I attended. All my siblings had attended this district ahead of me, and we always used my dad's company address as our bus pick-up/drop-off. Sometime around 8th grade we sold the shop and moved to yet another house/district but had no intentions of moving schools, when one day I get called to the principal's office and notified that they "received a tip" and thus hired a PI to follow me home. They let me finish the semester, but then I switched to the proper district after that. Looking back, I have no idea why there was such a resistance to switching schools...
You Gotta Go, Bro
Not a PI, but have a short story about one. I live at the end of a cul-de-sac. From the edge of the circle there is a spillway that lets water drain out to the main street, which runs perpendicular to my house. No one parks on the main street because it is walled off to enter the complex.
One day this dude pulls up in a black car, parks across the street from the spillway and just sits there. FOR HOURS. Since this is not normal activity in the neighborhood everyone is immediately suspicious. He eventually leaves after doing nothing but sitting in his car all day so we all just forget about it until the next day he comes back and does the same damn thing. Someone finally called the cops and they came to suss out what he was up to. Turns out he was a PI casing someone in the complex. Cops told him to move it along he was making the residents nervous. Dude was not very good at his job since his arrival and subsequent non-activity only served to make him extremely conspicuous.
I used to do background checks for employment. The funniest one was a guy who was working for a large provincial hydro company. He relied solely on GPS. He had to drive to a remote site a few hundred kilometers away. The next day, the crew were waiting on him. Finally the foreman (the person giving the reference) calls to see when he would arrive. The applicant answered, sleepily and said his GPS signal stopped about 250 km in and he just turned around and went home. Didn't call anyone, use a map, just went home. He also used to take a little boat pretending to survey sites. Several times he was caught sleeping, just floating around in the boat.
The most surprising thing: he got the promotion he was seeking.
A Complete Misfire
I know someone who was a junior detective. apparently, as fiction as it sounds, the guy had been cheating on the wife with her brother. but she said she didn't have a brother at all, and grew up as an only child. so naturally, they were really curious to find out who this "brother" of hers was. when they questioned the husband, he said that the guy who claimed to be his wife's "brother" said that "we've known each other for so long" and "i grew up with her" and all that jazz.
at first they assumed it was probably a long lost brother or something, but then when the husband was asked to describe the guy, he described the wife's father. according to the wife, her father wasn't there during her wedding and was replaced with her uncle instead. i'm not sure if this was interesting, but i somehow found it fun.
Roller Coaster Of Emotion
My dad caused a car accident when I was little (rear ended a guy stopped around a blind curve). The guy claimed back injury and sued for some crazy amount, like $300k or something. Not sure if my dad hired a PI or did it himself (I was 5ish?). But got the dude on film lifting 50lb boxes at his workplace. He died of unrelated causes shortly after and the lawsuit got thrown out.
I've hired a few for insurance fraud. This one guy was amazing because he was one of those adults who looks like he's 18 up until he's 35.
One claimant was running a window tinting business out of his garage while off work for his injury. PI hired him to tint his car windows, and told him "My camera's acting up, so I'm going to sit over here and try to fix it while you tint the windows." Footage was amazing.
Another time he followed a claimant to a local festival, and saw him dancing around. He went over and told him he was filming people for a high school class project and asked if he could get video of him dancing. The guy happily agreed.