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Every job has its perks and most of us just want the good stuff 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 18 chauffeurs are totally indulging us, y’all, and these stories are everything you want and more.

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.

17. 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.

16. 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.

15. 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…

14. 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.

13. 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.

EDIT: Boyfriend and groom were NOT the same person.

12. 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 over heard a lot business deals with absurd amount of money referenced. Like 10’s of millions.

11. 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.

10. 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.

9. 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, etcera. 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 Dep’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.

8. 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.

7. 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.

6. 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.

5. 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.

4. 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.

Some highlights:

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.

3. 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.

2. 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.

1. 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!


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