No matter what our lines of work could be, there are just circumstances we can’t avoid. Being with affluent people as a chauffeur or just any worker, we couldn’t really escape the moments where we encounter their most awkward, exciting, and some of the juiciest events of their lives. Thus, sit back for here are the 30 stories of the weirdest and most shocking encounters with wealthy people from our Reddit community.
#1 Panic mode, on!
A friend of mine worked for an upscale concierge chauffeur service. His most memorable moment came when he lost Marie Osmond. Fairly simple gig, go to the airport and pick up Marie Osmond, who was to be the featured entertainer at a private event. The plane comes in, he meets her, she has a carry-on bag but her checked suitcase, containing her stage dresses and makeup, is missing.
She is unflappable, though…asks to be taken to the nearest upscale mall. He does as instructed, she goes into a large upscale department store, selects two long sequined cocktail dresses, and goes to the fitting room to try them on (without him, of course).
Unfortunately, there are two entrances and exits to the fitting room, and Marie Osmond exits out through the other side and cannot find my chauffeur buddy, who is waiting patiently on the side she’d entered…20 minutes passes. He thinks something has gone wrong, so he grabs a female manager and asks her to go into the fitting rooms and ask for Marie Osmond. The manager thinks she is being pranked and declines.
Chauffeur buddy is in a mini-panic mode now, running wildly around the store asking random customers “Have you seen Marie Osmond? Have you seen Marie Osmond?” Store security is summoned and he is asked to leave the premises right NOW, He calls his employer and tells them he has lost Marie Osmond. The employer doesn’t have her cell phone number but has her agent’s number and he is not accepting calls.
She has in the meantime taken a cab to the gig, thinking she has been forgotten. Lots of apologies eventually ensued and there were no repercussions. —MastadonBob
#2 Two million dollars wedding
I once worked at a really exclusive club in Massachusetts, the kind you have to be born into and/or have generational wealth to be voted into membership by the board.
Someone got married at our club and spent over 2 million on the wedding. They flew out the event planners for Coachella to design every aspect of the wedding. It was a spectacular wedding and one of the most fun nights I’ve ever had. However, something happened that left me in awe of the lifestyle rich people had. After spending all that money on a wedding, at the end of the night, the front desk saw the groom go home with one of the bridesmaids instead of the bride. —Current_Elk_550
#3 Unfortunate life
When we were in high school, my friend used to caddy at a local country club. One guy really liked him and asked if he would be willing to drive him around while he went out partying (this was like 2003 and in a pretty rural area), my friend agreed.
He picked the guy up at like 8 pm. Right off the bat, the guy handed him $200. He went to a bar for a little bit, my friend sat in the car. The guy came out, handed him another $200, and told him he had to visit his “friend” real quick. He went and got a bunch of coke.
They went to another bar, he handed my friend another hundred dollars and told him to look out the window and turn up the radio (he then blew several lines).
He came out a couple of hours later with a girl (he was married with kids). He handed my friend another $200 and they went back to her house. After they had sex, he came out and asked to be taken to the beach.
At this point, it was like 2-3 am. My friend said that the guy slowly walked around the beach, went into the water up to his ankles (in his shoes), threw a bunch of rocks into the water, and then sat in the sand for about 45 minutes.
He came back to the car and asked to be driven home. When they got out of the car he hugged my friend and gave him $500 and asked him to never tell anyone what happened.
None of us really believed my friend when this happened until the guy he drove got arrested for assault and possession of cocaine like 6 months later. —PrometheusAborted
#4 Gain millions in pandemic
I’m not a chauffeur but I personally work for a billionaire, one on one in his home.
His wife was on the phone with a friend and I overheard “Husband has done so well in this pandemic – we’re up $330 million! I guess you must have made out pretty well, too, eh?” (As wealthy people generally keep company with other wealthy people…).
This was hard to hear especially with people losing their jobs and homes, left and right. —NormalPressure5
#5 Living the life
Picked up a wedding party: bride, bridesmaid, and bride’s boyfriend who was paying for the wedding. They had a magnum of champagne and we drove around for quite some time while they snorted some white powder in the back. They were using rolled-up $50s and $20s, then tossing them to me in the front seat as tip money. I dutifully brushed off each bill and added them to my wallet, pretending not to know what was going on.
The “couple” argued off and on about showing up to the wedding, apparently, she felt weird about getting married and he was trying to convince her it was a good idea.
Finally dropped them off at the church and he slipped me a matchbook with his name and number written on it.
However, the real kicker was that the boyfriend was not the same man she was getting married to. I could not believe my ears or eyes.
Yeah, it was the late 80s and I was a young woman, one of the only female limo drivers at the time in that city. Scored a sweet leather jacket with the tips from that night.
So many weird stories. —Proper-Beach8368
#6 Netflix producer
Buddy of mine ended up picking up a Netflix producer while doing uber. He said they had a great conversation as he brought him to his hotel. The producer invited him up for a drink and since my friend was a film student he thought it’d be a good idea to go and try to get some good networking in. They hung out for about an hour when he asked my friend if he knew of any massage places with “happy endings”. He didn’t but the guy paid him $500 to bring him to the closest massage place which was only a few miles out. Upon dropping him off he gave my buddy a card and said “there’s a big party/festival I’m hosting. That’s your ticket in. I’ll let you know then if I get that happy ending haha!” —catsandtats001
#7 Firing employees
Not mine, but when he was in his 20s (think postwar England) my grandad used to chauffeur this businessman around quite a lot. He was pretty tight with his family, used to play with the guy’s kids a lot, etc.
One evening this guy gets a phone call in the car (a big deal back then) and it’s pretty serious. My grandad pulls over and asks if he should step outside the car. He says ‘No you can stay, but you never heard this conversation. My grandad sits there while this dude fires thousands of employees. He said he wanted to dissolve into his seat forever.
It’s been a while since I heard the story last so I’m lacking detail but that’s the gist of it —PowderPhysics
#8 Free tickets
I used to drive limousines and taxis. One time I got the manager of a fairly famous Canadian band in my car asking me ‘where’ to buy drugs. I had no idea where and I told him that, so his bright idea was to find a call girl, hire her and ask her. I told him I couldn’t help him pick up call girls either. He was disappointed but understood.
He had me drive down a well-known street until he saw one. He asked me to pull over, got out of the taxi, paid the fare, and then immediately flagged me down again as a ‘new ride’. I knew what was up, but whatever. He gets back into the car with the woman and she tells him exactly what house to go to for some drugs. I take them there and wait a bit, they come back out and I drive him back to the venue.
Then he offers me two free tickets to the show which I gladly accepted as I love that band and had seen them 3 times. Alas, since I was still working during the show, I gave them away to two friends who had never seen the band. They had a good time and I had a fun story to share with them about how I scored those tickets. —Achaern
Basically, a guy I used to know back when we were teenagers (17yrs old) had a lot of money. We just never knew how much until I was invited to go on holiday with him and some other friends, all expenses paid of course. Anyway, we took a taxi to an area where this guy wanted to buy an apartment and wanted to show us so we went with him and ended up spending the whole day walking around the area. We got tired and eventually wanted to go back to the house but we were so far away that walking was not an option unless we wanted to walk for about 3 hours. Neither of us had enough cash to pay for a taxi, and back then taxis didn’t accept cards (this was around 2000 or 2001 btw) so this guy rings his dad and asks if he could send a chauffeur to pick us up, but the chauffeur turns out was busy doing some deliveries for the dad, so instead the dad says “there’s a Mercedes Benz dealer shop near where you are, I know the manager there as I’ve bought several cars from them, just go there and buy a car with the credit card. You can leave it in the house and we’ll figure out how to bring it home later.” So we went to this dealer shop and somehow in about 30 min the manager did all the paperwork and we ended up driving back to the house in a brand new Mercedes C class, which we used for the rest of the holiday. —ohwow234
#10 Securing a deal
Use to drive uber in DC early in the morning. About three years ago I picked up a guy in the Georgetown neighborhood at a really nice house. He was clearly someone who thought he was important because he was wearing like a $3,000 suit that had a pocket square and stuff. I was driving him a little way to the airport. This isn’t the closest DC airport but it is the closest airport that allows private charters. He took a call while he was in the car and kept saying “I told him we wouldn’t do less than 23.” Additionally, he was adding in things like “he thinks blah blah (technical terms that I didn’t know the meaning of and have forgotten) is worth no more than 500 million” or that “blah blah wasn’t worth more than 200.”
I was curious about what he could have been talking about given those sums of money. I tried to do some googling and couldn’t find anything. A few months later a DC company bought GE healthcare for like 21 Billion… I think the guy in the car was discussing that deal. —[deleted]
#11 Drunk students
Drove L.I.M.O. at Marquette University during undergrad and grad school. Some of the students that went there were obscenely wealthy. Limos are the vans that drive drunk students anywhere on campus and a few blocks outside of campus.
One drunk guy leaves his wallet in a van and another driver calls it in, so I and another supervisor can take it to campus police. We pick up the wallet from the driver and open it to get the student ID so they know who to email. My eyes almost fell out of my socket upon seeing the content of the wallet. There had to be a few grand in there. I don’t think I have seen that much cash in one wallet before. When we called the kid to tell him about it he told us we could just keep it because it was too far from his dorm to bother picking up. K. —prailock
#12 Rich dressed like poor
I had a Russian friend and I’d always just generally assumed he was at our university (in Scotland) on some kind of scholarship. Seemed to only own one set of clothes, was top of the math program, and drank a lot of vodkas. He did once try to sell me a submarine when he was drunk, but that happens to the best of us.
All seemed to fit until his dad shows up and they flew to Paris for lunch. —grahamsz
#13 Model problems
My sister was in a limo once and asked the driver about his most interesting ride. The driver said that he picked up some models who were going to a PETA demonstration, “I’d rather be bare than in fur” or whatever it was. He got to the location, they stripped naked in the back of the limo, and he waited until they were done with the photo op. —mcgato
#14 Oops, wrong car
This was a recent story in Australia. A father drops his family off at the entrance to the restaurant as it’s raining. A bunch of guys jump in thinking he’s their Uber driver and he just goes ‘oh, stuff it’ and takes them where they need to be.
Halfway through the drive one of them realized who the driver is. It’s former Prime Minister Kevin Rudd. Then a series of contrite apologies followed, but he was a good sport about it. 1Lozzif
Not a chauffeur but I did some work in the cottage of a very high-profile Canadian businessman. I was working in the room adjacent to his office listening to him absolutely BERATE Stephen Harper (Who was the Prime Minister at the time) over the phone. He talked down to him like he was scolding a 10-year-old for 30 minutes. Made me realize who really holds the cards, and it isn’t the politicians. —Morganvegas
#16 Out of touch multimillionaire
Wasn’t exactly a chauffeur but I did have the distinguished privilege of working with a multimillionaire one time for a couple of days and I was just astounded at how out of touch he was with people.
In one conversation he was talking about how he hated all the new homes they were building and he liked old castles so he was having a castle in Scotland disassembled and reassembled here in the US piece by piece.
On another occasion, he asked me why I wasn’t in college yet (the job was after high school and I was working as a plumber) and gave me an “Ohhh right” when I told him I couldn’t afford to go yet and had to save up. —whoreychan
#17 Top-tier richness
So, I had met this kid at summer camp a year earlier and we became really great friends. We were into the same things, both had a weird sense of humor, both hated the same really annoying camp counselor, basically inseparable. The next year before we went back to the same camp, he invited me to go with him from the camp to a beach house on an island off of the NC coast that his parents co-owned with another family. The plan was for his parents to pick me up and we would drive to the airport where my friend’s dad would fly us to the island on their private jet. I forgot to mention that they were incredibly wealthy.
So, the week before camp, the plane crashed (nobody was hurt but the plane was destroyed). I thought that the vacation plan was probably over or at the very least going to be quite different. No, they just bought a new jet. They didn’t charter it or rent it or drive us to the ferry to the island that costs, like, $15 per ticket, they bought a new jet because “it was about time for an upgrade anyway.” Not that I’m complaining, that jet was awesome, it’s just crazy to experience firsthand that level of wealth. —ImWastingTimeOnline
#18 Friendship goals unlocked
About 25 years ago I had a summer job at a very ton-y country club. Six-figure joining fee, five-figure continuing membership dues, and that got you nothing but the privilege of paying top dollar for rounds, food, etc.
I was a porter some of the time, as we had cottages on club grounds for members to stay and make a weekend of it. One of my duties was driving members to and from airports – usually private airports for private jets.
One time I’m driving two guys to the airport, and one of them starts complaining. Seems he and his wife are always fighting over who gets the jet every weekend, and where they want to go.
Well, the other one replied, my third jet is actually just gathering dust right now since my son went to college. Wanna take it off my hands?
They shook on it right there in the van. —letsryan
#19 Mafia’s way
A small part of my family was Chicago Mafia.
Grandpa told me a story of a family wedding in Chicago they went to in the late ’60s. They were picked up at the airport by a limo with some high-ranking family members.
On the way to the hotel, they were stopped about 8 times by various police officers. The officer would walk up to the driver’s window. The chauffeur would reach into a money bag and pass a bill to the officer. Nothing would be said and they’d take off again.
Eventually, my grandpa asked if they were being bribed. His cousin (mafia) laughed and said, “No it’s Thursday. That’s when we pay our boys.”
So I guess that’s how they did it. Looks like a traffic stop and in the open where its not unexpected.
So I’d imagine that chauffer had seen some things. —Blue_OG_46
#20 Armored limo
My uncle was a Teamster. One of those Teamsters. I didn’t understand it when I was younger, but we’d go to Reno or Vegas, and never have to pay for anything. We wanted to go on vacation, he’d get someone to give us a vacation home to stay in.
Anyway, we go home to Hawaii one year, and we’re met at the airport by a limo. Kid me thought this was amazing since I’d never ridden in one before. Had a ball. But I couldn’t figure out why my dad, one of the most laid back, salt of the earth, blue-collar guys you’ve ever met was scowling and looking around like his head was on a swivel.
Years later, I found out it was an armored limo. Some rivals had firebombed my uncle’s car, and he took no chances that we’d become targets. I remember that vacation as being fairly normal, except for the limo and my uncle coming over with more “colleagues” than he usually had with him. —LadySiren
#21 Weirdest encounter
I was driving an Uber and there was the weirdest guy I picked up from a dispensary. He was really good-looking, very well dressed, and clearly well-to-do, but he was in some kind of mental distress. He wanted to visit more dispensaries but had clearly already bought the max. I got his hotel information through conversation and went there instead. On the way, he told me (in all seriousness) all about how his father was God, which meant he was Jesus. “Didn’t you notice how much brighter the sun became when I got in your car?” He was serious. He also followed guns n roses like they were the grateful dead, he thought Axle Rose was the smartest man alive. He didn’t really notice when we got to his hotel instead of the dispensary. I did ask him if he had taken any other drugs that day and he insisted he hadn’t.
That was also one of the weirdest. —kry1212
#22 Patience is a virtue
I used to work for a private transportation company, started my own chauffeur business last year.
Couple of things right off the top of my head that come to mind but the worst had to be a really snobby family from another mountainous state coming to our state. The entire ride to their destination was spent talking about how much better their state was. Towards the end of the ride, the mother started cutting her toenails in the company vehicle. No idea how to react to that situation. Basically just had to let it ride. —AustinSomething
#23 Well-off complaints
Once I was in a home selling for over 10 million with two Bentleys in the garage. I overheard the homeowner talking to her friend in the next room. “These new tax laws are killing us in the middle class, we had to open another trust just to save more money this year” insane that this woman really believes that she’s the middle class.
Another time in another multi-million dollar house. The homeowner said to me “The billionaires are pricing us, millionaires, out of the neighborhood” she was referring to her gated community in Park City and I was apparently supposed to feel sorry for her.
One time, I walked into this large home and said “is there anything special about the house you want to make sure to feature?” The homeowner said, “no I don’t think so pretty average.” So later walking around alone in the basement and I see a shut door I open it and see a staircase leading further down, I hit the light switch and at the bottom of this narrow staircase I just see this blonde-colored wood floor. I walk down the stair to a full-size regulation basketball court under the basement… nothing special though. It also had a mezzanine with a set of seats looking over the court and an arcade on it. —LifeWithAdd
#24 Rollercoaster of emotions
One time I was driving a young woman and right before the destination she screamed for me to pull over. When I asked her what was wrong she pointed to the couple that was kissing in front of the building. Apparently, the man was her fiancé. She didn’t get out, she didn’t cry, but she did ask if I could take her back to where I picked her up. I’ll never forget her face, it was the saddest face I have ever seen in person.
Another time I was picking up a group of guys outside a club early in the morning, and as the first guy stumbled in a Glock fell out of his coat pocket. We just locked eyes and I said, “hope that’s not for me haha”. I was nervous and didn’t really know what to do/say.
Probably my favorite was picking up two college-aged girls from what I can only assume was a party. They were very drunk, and the second girl was basically completely gone. They were going all the way to Ridgewood, which was almost an hour. Girl A was pretty talkative and funny, girl B looked to be completely passed out/sleeping and didn’t move the whole trip. We made it to Ridgewood, and Girl B sits up suddenly, looks around, opens the door, and vomits everywhere. She seemed fine after that, but I just kept thanking her for making it the whole way and not throwing up all over my car. —close_thelid_grillme
#25 Working with an OG
I was a driver/bodyguard for an OG, rich Chinese guy who came to Canada in the 90s. During a drunken drive home he told me his birth story… his mom was an artist and one of the top officials in the CCP had an affair and impregnated her. Magically she had papers to immigrate to any nation she desired.
Later, he told me that he and another rich Chinese friend planned to steal the money his dad was going to give him to pay for his four-year college program, move to the city the school he was “accepted” to, and trade penny stocks, and find a virgin call girl. It was the first time I got a double shock. —br0wnb0y
#26 Invisible driver
Many years ago I had a security job that included among my duties the occasional responsibility of driving our rich clients around. I would typically drive them in my employer’s Cadillac Escalade that we had for those types of requests so there was no divider between the front and back seat like in a limo.
These were mega-rich people who treated me politely but quickly forgot I was present. I overheard conversations about lots of shady and illegal financial stuff. I overheard clients talking about insider trading, embezzlement, price-fixing, and stock pumping.
I also heard some speaking openly about extra-marital affairs, sexual exploits, and expressing racist, sexist and homophobic attitudes. All of this was done with me sitting a couple of feet away in the driver’s seat like I was a piece of furniture instead of an actual human being with ears. —throwawaylogin2099
#27 Taylor Swift’s basement
Not a chauffeur but I worked as a busboy for a very rich country club. I know it cost at least a couple hundred thousand for continuing membership fees. I constantly had to be going from table to table while the rich people were dining and I would overhear snippets of conversation. One day, while busing tables, I heard one group of younger adult men talk about how they broke into the basement of one of Taylor Swift’s homes. I think I missed a step after I heard that one. —shelfshelf
#28 10 mins worth
I was driving the CEO of a large company around to a few meetings. As soon as he got in the car, his phone rang and I overheard him spend about $30 Million on a collection of “a few” old Rolls Royce cars.
$30M spent in less than 10 minutes. I could not believe it and I somehow envied him. —marcwithnok
#29 Stuck seagull
I was a driver for a 4 star General in Europe and drove him and his family around in an armored BMW. One day I drove him and his wife to the airport. It was very quiet as we were on the highway cruising at a good speed. Everyone was looking straight ahead. I noticed a very large white bird (seagull perhaps) on the side of the road, and right when I was about to pass it, the bird suicided himself on the front bumper at around 90mph. Feathers were abounded and a muffled thud filled the cabin. My eyes briefly went wide. Everyone saw it, and nobody said a word for the entire trip. At the airport, I got out to check for damage but didn’t see anything. About a month later the vehicle went in for service and the bird was found stuck to the radiator. —Ov3rtheLine
#30 Kidnapped passengers
Done private security overseas and some domestically for a lot of Business folks when traveling in sketchy parts of Asia, lots of movie/pop/reggaeton stars in Latin America, some short domestic trips when Latin big shots come to the US to visit and don’t want Cuban/Colombian/Haitian/Mexican Mafia/MS 13 to take a shot at them while traveling to Disneyworld.
The craziest thing I’d overheard besides sex stuff, is 1 guy told me I was hired because he was kidnapped last year and didn’t want to get kidnapped again…I obviously took the bait and said, “Dang man, how long were you kidnapped for?”
He replied, “14 hours, but that’s because the bank manager wouldn’t open up the bank at 11 pm to get the 2 Million Lempira out. I could have gotten out in an hour if it was daylight.”
I don’t know if he was pain delusional or just that confident. —food5thawt