All jobs have their perks, along with the things that aren’t the best, and most of us just want the good things to outweigh the bad. In the case of people whose job it is to drive rich people around town, I have to think that the things they overhear and/or meeting cool or famous folks has to be high on the “good stuff” list.
At least if you’re nosy, which…how can you not be?
These chauffeurs are totally indulging us, y’all, and these stories are everything you want and more.
1. Oh, right, that kind.
Not a chauffeur, and I was a participant in this conversation.
I used to tutor an oligarch’s daughter in Rublevka, the wealthy suburb outside Moscow. One day she mentioned that she likes to ski. I asked her which kind of skiing she preferred (downhill is more popular where I’m from, but cross-country is quite popular in Russia; it’s even part of some schools’ curricula).
“My favorite kind of skiing is the type where you jump out of a helicopter.”
Silly me, I forgot about that kind….
2. Different strokes.
I am late to the party but I can absolutely contribute to this thread. Used to work for a private transportation company, started my own chauffeur business last year.
Couple things right off the top of my head that come to mind:
had a really snobby family from another mountainous state come to our state and 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 TOE NAILS IN THE COMPANY VEHICLE. No idea how to react to that situation. Basically just had to let it ride.
Probably one of the wealthiest people I’ve ever met in my life was a gentlemen who was a very high ranking member of Scientology. Was also one of Bill Gates’ close business partners. Never in my life have I been treated like I did not exist until that ride. Barely even got his name before he asked not to speak for the almost 2 hour ride.
Just previously I drove an NFL all-star and he was one of the coolest people I’ve ever met which was super refreshing. All I ever heard of celebrities, particularly athletes, was that they could be very rude. Guy was just a regular ass homie who gets paid 15 mil a year.
3. His third jet.
About 25 years ago I had a summer job at a very tony 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.
4. You know these realtors see some s**t.
Not a chauffeur but I work in high end real estate so I’m in the homes of the affluent a lot.
Once I was in a home selling for over 10 million with two Bentleys in the garage. I overhear 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 referring to her gated community in Park City and I was apparently suppose to feel sorry for her.
5. So many jobs I didn’t know about.
I once worked with a guy that was a utility worker but also a trained pilot. He was getting ready to retire from utility work and had been offered a job by a company that basically repos private planes for the bank when the payments are too far behind.
He said he considered it but decided that a job repoing 30 million dollar planes was maybe not the safest job for someone his age.
I never knew before that conversation that such an industry existed.
6. A rude awakening.
I had a job as a runner. I would pick up music artists from the airport and drive them to the venue, among other things. I won’t name the artists, but I picked up one duo from the airport in an Escalade. It was raining heavy that day and I had the windshield wipers on next to full. It created a beat.
One of the guys has a small, hand held sampler and starts making beats in time with the windshield wipers. All of us were driving along, bouncing to the rhythms. It was sweet. Another time, I was driving a famous songwriter/guitarist back to the airport after the gig with his family in a 15 seater van. His family was telling him how great he was, but dude is old.
All he could say was, “What?” and “Huh?” It dawned on my he couldn’t hear. Bob “Percy” Plant can’t hear s**t. I have a ton of other stories, including how I got involved, but I’m not sure if anyone wants to hear them.
7. These are the kinds of friends I need.
This reminds me of the time that I went on vacation with one of my friends from summer camp a while back.
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.
8. That is not a good day at work.
Not sure if I qualify, but I did drive uber black for a while in NYC.
Had a few interesting situations.
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.
9. You can’t buy your way out of that.
I’ll answer for my grandparents.
They owned a limousine business, I believe in the early 2000s, and my grandmother drove Mel Gibson around.
She said he was nice and that he had requested to sit in the front passenger seat due to car sickness.
10. His birth story.
I was a driver/bodyguard for a 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.
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 prostitute. It was the first time I got double shock.
one of the last major conversations I have working for him was how dark skinned people are scary, so it’s not racist, that Chinese people as a whole view it like that and no sensitivity/racism training would explain it well enough to make Chinese people as a whole change their mind. I asked him how it was that he hired me, other than being scary… two weeks later he replaced me with two big white guys.
11. Some things he can never, ever talk about.
Not a chauffeur.
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 60’s. 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 drivers 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 its Thursday. Thats when we pay our boys.”
So I guess thats how they did it. Looks like a traffic stop and in the open where its not unexpected.
So I’d imagine that chauffeur had seen some things.
12. Sometimes they’re nice guys.
My collegiate baseball coach was a friend of Toby Keith and got him to visit one of our fundraising golf tournaments. I knew little to nothing about either golf or Toby so I was completely out of my element, but Toby was nice enough to show me how to drive a golf ball. Turns out the guy is extremely nice.
So nice was he that we lost our coach the following year as Toby financed our coach to again pursue baseball (he never made the show and gave up after years in the minors due to family). So, Toby just paid for the housing, food, and everything so this other guy could pursue his childhood dream.
I guess that’s somewhat related. Rich people. Golf. So, there you go.
13. This checks out.
Not a driver, but I used to caddy at a fairly exclusive country club in Massachusetts. It’s the kind of place where, no matter how rich you are, you can’t buy a membership. You’re either born into it or you marry a member.
As a result, a lot of the members like to show off their influence by inviting guests who would otherwise be unable to play at the club.
Someone invited Mitt Romney.
We were given a heads up that the governor (he wasn’t a senator yet) would be coming and they wanted us to know how to act around him. We were told he wanted to be treated like anyone else but they didn’t want us to gawk. So, I guess to make sure us dumb caddies weren’t gawking, we were instructed to not look at or acknowledge the governor.
Because this is precisely how we would treat other people.
I did get to shake his hand and chat a little bit. He was friendly, personable, way nicer than a lot of the members. I still don’t like a lot of his politics but he seemed nice enough in person.
14. Not a piece of furniture.
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, s*xual exploits and expressing racist, s*xist and homophobic attitudes. All of this was done with me sitting a couple of feet away in the drivers seat like I was a piece of furniture instead of an actual human being with ears.
15. Weirdest ride ever.
I was driving as Uber and I picked up two business men in an industrial park.
They were building developers. The man who was clearly the boss spoke to me as if I were a man and I was always the driver who picked him up.
Although they were clearly from the middle east, they chose to speak English. Maybe they thought it was rude not to, being in the US? But if that would have been rude I’m not sure what the rest of the conversation was…
They spoke about the future of business as if it were all so futile and how everyone will be either very wealthy, like them, or very poor, and how their children really won’t be able to get jobs either but also won’t need to.
I logged more than 4000 rides between 2015 and 2017 and that was one of the weirdest.
The other 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.
16. This honestly makes me sick to my stomach.
Not a chauffeur but worked as a caterer for private jets and the insane folks who owned them. Had a huge order from what I knew to be a smaller jet so I really wondered about it. When one of the owner’s handlers was training a new flight crew, he ordered $12k of meals for a flight that didn’t exist just so the new flight attendants could practice the fine points of checking in a catering order.
I listened outside after the food drop as the handler started explaining what to do to six of the most beautiful humans I have ever seen.
We provided food for a lesson! The food was wasted. I found it in the dumpster outside one of the hangars the next day
17. That’s a bunch of bs.
Not rich or famous, but I drove Lyft for a few months.
I picked up a group of 5 bankers from their holiday party, each wanting to be dropped of individually but promised to “make it worth my while.”
Tip was $2.
18. I don’t think I could ignore that.
Not a conversation and not me, but definitely weird, shocking (and disgusting).
A friend of mine who worked in music was in a limo with Robin Thicke and a load of dancers and models driving round London.
They’re all just chatting and whatnot, and out of nowhere, Robin Thicke just starts going down on one of the models.
There was an awkward split second silence, and then everyone just carried on and ignored it.
19. What in the actual heck?
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 were 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.
20. Good thing he wasn’t a cop.
I used to drive limousine and taxi. One time I got the manager of a fairly famous Canadian band in my car asking me ‘where’ to buy coke. I had no idea where and I told him that, so his bright idea was to find a prostitute, hire her and ask her. I told him I couldn’t help him pick up prostitutes either.
He was disappointed but understood. He had me drive down a well known street until he saw a prostitute. He asked me to pull over, got out of the taxi, paid the fair, 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 prostitute and she tells him exactly what house to go to for some coke. 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 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.
Not really a shocking conversation and hardly a famous person, but it was interesting how easily and full of trust people can be about searching out and buying drugs in a strange city. For the record, this was 2003.
21. A story to tell forever.
Billy Bob Thornton was doing radio press for a movie about to come out, meaning he had to stop by 6-7 radio stations for interviews. He wanted to have a cigarette in the vehicle on the way to the next interview but I had to let him know our company has a no smoking policy in our vehicles.
He asked me to call the owner to make an exception but the owner said no and its a $250 cleaning fee if he smoked in the vehicle.
He asked to stop by a bank, Came out and handed me $5,000 cash and said “here’s for the whole Go**am pack”
He smoked in the car the rest of the trip. Later I got up the nerve to ask him if that’s the most expensive pack of cigarettes he’s ever smoked? All he said was “not even close” (never explained it further)
I think about him often…
22. That sounds right.
My dad was a chauffeur when I was younger and he told me of one story driving the director of a company down the road with the Blackpool illuminations in the company limousine.
The director was standing up out of the sunroof with his arms out waving at people as he drove past.
What the people on the street didn’t know is that in the back of the limo there were 2 prostitutes blowing him.
23. You almost can’t believe it.
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 coke 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.
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.
24. I can hardly imagine.
I’ve have multiple people pay me handsomely to let them smoke weed in the car. Heard a French guy yelling at his wife that $10,000 was too much to pay for 2 bracelets that she bought.
Also overheard a lot business deals with absurd amount of money referenced. Like 10’s of millions.
25. The chickens always come home to roost.
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 8pm. 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 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 fu**ed, he came out and asked to be taken to the beach.
At this point it was like 2-3am. 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 like 6 months later.
26. A different college experience.
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. Couple things I remember randomly from it:
Drunk guy leaves his wallet on a van and another driver calls it in so me 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. There had to be a few grand in there and 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.
I picked up a couple girls from A Chi O and they spent the entire ride talking about how it was ridiculous that one of the girls’ parents planned on making her pay for her own apartment after graduation and there was nothing even livable under $2K a month. The school is in Milwaukee, Wisconsin.
Mardi Gras is the name of a campus ministry trip where you use your spring break to build houses and drink in somewhere that doesn’t get snow in April. One of the people on my van was getting a free night of drinks from his buddies because he paid for everyone’s trips. I think it was like $1,500 per person IIRC.
Rich kids are rich but foreign rich kids are usually on a different level. Was talking to a guy from Spain who said his dad did something with movies over there, idk. He had an actual rolex on and ended the conversation with “So anyways, do you know where to find any m**h?”
It is a free service and a frat star tried to “pay me” for the ride with a ziplock baggie of coke. I said no and he called me a legend and left a $20 in the cupholder before I realized it.
27. The money is crazy.
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.
Drew Barrymore was a frequent guest and there was always a lot of tension between her and her ex who always came with his extremely young new gf/wife. She wasn’t super friendly (no one was supposed to acknowledge they recognized her), seemed constantly stressed, and I felt kind of bad for her. Didn’t seem like a fun life. Mitt Romney, Morgan Freeman, and a bunch of big time Athletes were also frequent guests.
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, at the end of the night, the front desk saw the groom go home with one of the bridesmaids instead of the bride.
I helped set up and cater this one member’s garden party. A casual affair for them that must have cost tens of thousands. They had a well known music group come play for their guests and I got to play cornhole with said group during the luncheon which was pretty cool.
So many wealthy kids with rich kid problems and wildly different upbringings. Parents would constantly talk and quiz their kids on politics, history, science, etcetera. One group of guys was challenging their teenage sons to come up with a business idea. The boy with the best idea would receive a million for startup costs. Kids talked stocks constantly at the dinner table. Teenagers would come to eat with their friends, drink, and drop a casual $15,000 bill on their parent’s tab. Just such a stark contrast from the way I was raised, where money was a taboo topic and my weekly $2 allowance for a week’s worth of chores made me feel rich.
It was a small island with an equally small nightlife, so for fun, we would grab a drink and an ice cream cone, and hop on the yachts and sailboats parked at the docks. We’d explore and pretend we were sailors or captains for the night. Once we hopped on Johnny Depp’s super yacht while he was out at dinner. We actually managed to hang out for a hot minute before security finally kicked us off.
While looking for a tennis partner, I met this truly lovely couple who basically adopted me. I would bike to their house to play matches on their backyard tennis court every day. They loved to take me out to eat at these incredible restaurants (as a foodie, I was in heaven). They let me drive their cars on the beach, use their surfboards, drive their jetski (I ran out of gas in the middle of the ocean and had to get rescued by the coast guard), took me out on their yacht, and even flew me out on their private jet to nearby islands to explore in the morning (and would then fly me back in time for my job at the club). They were the most kind and wonderful people and never asked for anything but my company in return. I think they missed their daughters who both lived out of state. I fell out of touch with them but I think of them often and hope they’re doing well.
28. Just a normal guy.
This is not a limo story, but this thread reminded me of a rich guy story. My daughter played soccer for many years and at one practice, a guy drove up in a Ferrari, got out, and started talking to another of the dads on the team. After a few minutes, the guy left and another of the dads went over there and asked him who that guy was. He replied that the guy was his lawyer or something.
I come to find out years later, that that guy in the Ferrari was a multi-millionaire had one and only one client: that dad. And his only job was to handle the dad’s charitable donations. So this dude got filthy rich donating millions of dollars of somebody else’s money and taking a percentage off the top.
The dad, who was apparently worth several hundred million dollars, never came across as rich at all. He wore sweats to and was at every practice and game. He drove a Camry. Had been married to his average looking wife for like 25 years. Stuff like that.
Acted like a normal guy like the rest of us.
29. None of this surprises me.
My aunt was a driver for actors, mainly when they’d have shoots here in Oregon.
She drove Woody Harrelson around for a time and she said he smoked weed constantly and she was always worried she’d lose her job.
30. You just never know.
Not a chauffeur, but seemed like a good chance to remind people of the story of John Boehner (At the time, Speaker of the US House of Representatives, 3rd in line for the US Presidency) not knowing how to use Uber.
As the story goes, one of his aides downloaded the app onto his phone and showed him how to use it. Unknown to him, he’d been stuck on the carpooling option, uber-pool.
That’s what he used for years.
There are all sorts of tales of commuters hopping into their carpool and bam, there’s John Boehner stuck in a middle seat asking to get dropped off at the Capitol Building.
However you feel about his politics, I think that’s pretty funny.
31. Why is this so charming?
I used to know a Chauffeur, he ended up driving around some big stars.
He was big dude, like 6’8″ and super muscular.
His best story was when he was driving around a few WWE (WWF back then) stars, and they awkwardly asked him to not get out and open the door for them because he’d make them look smaller.
32. None of this surprises me.
One of my best friends used to drive Uber in a wealthy area of LA. He told me so many stories about drunk celebs and tiktokers in his car.
Someone offered him a bag of weed because they felt sorry for their friend throwing up in the back seat. Most people were just normal though.
Mike Tyson is apparently very nice in person and also a giant pothead
Somebody on Gossip Girl and her friend were arguing about chicken nuggets and tried to get him to go through a Wendy’s drive through during the lunch rush when there were 10 cars already in line
Addison Rae or one of her friends took their shoes off and left them in the car
Leo Dicaprio took more than 5 minutes to find the car. He seemed out of it and was quietly bobbing his head listening to music on his headphones.
33. Don’t lose your clients.
The memorable moment came when he lost Marie Osmond.
Fairly simple gig, go to airport and pick up Marie Osmond, who was to be the featured entertainer at a private event. Plane comes in, he meets her, she has carryon 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 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.
34. I don’t think castles were actually comfortable.
Wasn’t exactly a chauffeur but I did have the distinguished privilege of working with a multimillionaire one time for a couple days and I was just astounded at how out of touch he was with people.
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.
35. The life of the party.
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!”
He got the happy ending.
I love overheard conversations. They’re just so delicious!
What’s the craziest thing you’ve ever overheard?
Tell us about it in the comments!