I have always wondered what it must be like to be a driver.

You hear all the good gossip.

That's why when I'm in a cab or an Uber I talk quietly, just in case. You know someone is always listening.

So beware when you are spilling your tea.

Redditor Cicallis wanted to get the scolding hot tea from drivers out there by asking:

"Chauffeurs who drive around rich people, what are some of the weird/shocking conversations you have overheard?"

When I do an an Uber share I am always amazed by what people are willing to let people overhear. Like, do you not know you're still in public when in a car with strangers? I keep it jovial and not personal. Let's see what else our driver's witness...

Oh Billy...

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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 Goddam 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...


In the 80's!

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 doing drugs 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.


Reddit Users Share Their Best 'It's A Small World After All' Experience

The Caddy

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 drugs.

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 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 screwed around, 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.


Have you seen Marie Osmond?

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 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.


The Big Guy

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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.


Lord... that is a handful of mess. People need to get it together. And I knew Marie Osmond would always be a problem. LOL. Who else has some tales?

Happy Endings...

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!"


In the Car

I've have multiple people pay me handsomely to let them smoke. 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.



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He thought I couldn't speak French, heard him telling his wife on the telephone where she should order a strapon.


Get a Benz

Not a chauffeur but this happened because of a lack of one. 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.


In Fur

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 limo, and he waited until they were done with the photo op.


The Story of John

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.



I had a college friend whose parents were friends of Elmo Zumwalt, who told them a story about himself. Shortly after he was appointed Chief of Naval Operations, he went out for a jog on a foggy morning when he was new to the DC area, got lost, and had to hail a cab to get a ride home. The cab driver was friendly and struck up a conversation that went something like this—

Driver: So you got lost, what do you do for a living?
Zumwalt: I'm in the Navy.
Driver: I was in the Navy too! What do you do in the Navy?
Zumwalt: I . . . er . . . run it.

Driver: [shakes head].


Where to Begin?

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.

Some highlights:

  • Quentin Tarantino and Trisha Paytas were making out in his back seat when they were secretly dating lol
  • 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 b**chyfuxkjngbltch34

"Ohhh right"

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.


A Tip

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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.

In the van

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.


Flying Drivers

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.


Front Seat

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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.


I'm torn... I feel like I want to be a driver just for the writing material but I also fear for my life. How to weigh the options. The crazy is all comedy gold. I do know that for my next taxi ride... I'm gonna be mute.

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