Chauffeurs Who Drive Rich People Around Are Sharing The Weird Conversations They’ve Overheard

If you love to chat, being an Uber driver or a cab driver might be the job you need. Most people, however, don’t necessarily want you to speak while you drive them somewhere. The highest-paid drivers end up being much better listeners than speakers. Thankfully, they decided to let the world know how many weird and shocking things they’ve overheard while driving the rich and famous around in a car.

Reddit is often a great place to share stories. Hopefully, the questions asked on r/askreddit never get old, and we’ll be reading these true-sounding stories the rest of our lives. So what if they’re the stuff of innuendo and rumor. This isn’t a news site. This is meant to entertain.

Whether you believe it or not, you gotta admit, you believe these stories.

Here are the weirdest things chauffeurs have overheard while a rich and famous person was in their car:

1. Billy Bob will pay the fee.

“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).” –GoFox_97

2. Wild night.

“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 cocaine 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.

The boyfriend and groom were NOT the same person.” –Proper-Beach8368

3. The saddest, richest man.

“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 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 fucked, 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 of cocaine like 6 months later.” –PrometheusAborted

4. Ye olde Gatsby Party.

“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.” –Current_Elk_550

5. Know your role and shut your mouth.

“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.” –SayNoToStim

6. I’ve lost my celeb. Help.

“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).


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.” –MastadonBob

7. It’s all about who you know.

“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.” –catsandtats001

8. Blurred boundaries.

“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.” –beenybaby87

9. In the market for something off the menu…

“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.” –Achaern

10. You never know what’s going on underneath.

“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.” –mattmu13

11. Good for them!

“He thought i couldnt speak French, heard him telling his wife on the telephone where she should order a strapon.” –Puddle_Boots

12. Better tip big.

“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.” –icd1222

13. No fur, no problem.

“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.” –mcgato

14. Jump in the pool. The water is fine.

“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.” –WatchTheBoom

15. The secret is out.

“Quentin Tarantino and Trisha Paytas were making out in his back seat when they were secretly dating.” –bitchyfuxkjngbltch34