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If you think your driver isn’t listening in on your conversation, well…you’re either super naive or so rich, famous, or powerful that you just don’t care.
In the case of these 17 chauffeurs and the things they’ve overheard from the back seat, it seems to be a little bit of everything.
No matter the reason for people choosing to do things or say things in front of a perfect stranger that could get them arrested (or worse), I sure am glad – because now we all get to hear about them, too.
Let’s take a look!
17. The 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
15. 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.
14. 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).
Her answer?
“My favorite kind of skiing is the type where you jump out of a helicopter.”
Silly me, I forgot about that kind….
13. 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.
12. 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.
11. 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.
10. 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.
9. 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.
8. 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.
7. 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.
6. 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.
5. 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 then being scary… two weeks later he replaced me with two big white guys.
4. Some things he can never, ever talk about.
Not a chauffer.
A small part of my family was Chicago Mafia.
Grandpa told me a story of a famiy 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 chauffer 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.
3. 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.
2. 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.
1. 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.
People are astounding, y’all. Sometimes in a bad way, but not most of the time.
What’s the wildest conversation you’ve ever overheard? Share it with us in the comments!
