30 Chauffeurs Share The Weirdest Moments They've Experienced While Driving The Rich And Famous

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.

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.

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...

Not a chauffeur, but at a time I worked as a “lux” Uber driver.

I had a fascinating conversation with a gentleman whom I picked up from the airport whose job it was to break into casino vaults around the world and help them improve security.

He went into extensive detail about how the most recent vault he broke in to, the Bellagio vault in Las Vegas. It started with access through a construction entrance, he then climbed through an open window, jimmied a door open, found an unattended security pass and strolled into the vault.

While it wasn’t exactly a “stroll,” he told me about some of the “old” security measures including false rooms with doors that would seal behind you, infrared camera, laser trip wires, complex locks, finger print scanners, etc.

He then took a selfie from the inside of the vault, sent it to the head of security with the caption “is this your vault!?” The head of security was promptly let go. He showed me the selfie!

For those curious what the inside of the vault looked like, it was surprisingly similar to the vault in the movie “Ocean’s 13.”.

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 [illegal substance] 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.

Reverse story. My wife and I were the passengers. The Lyft driver was a former TV anchor man from Venezuela, and had to flee the government. He showed us videos of a new show on his phone.

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 [illegal substance].

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 f****d, 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 [illegal substance] like 6 months later.

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 w**d constantly and she was always worried she’d lose her job lol.

Not me, but my friend told me he drove someone in an Uber from a private airport to a gigantic house in town. During the trip she told him she had never been to a grocery store or basically any other department store.

I was driving the CEO of a large company around to a few meetings. As soon as he got in the car, his phone rang and I overheard him spend about $30 Million on a collection of "a few" old Rolls Royce cars.


$30M spent in less than 10 minutes.

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, sexual exploits and expressing racist, sexist 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.

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.

1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

I drove the Chancellor for a large University around and was told to actively forget everything I heard in the car. Throughout my undergrad career I constantly heard about massive cuts to the Humanities and Fine Arts budgets because we simply didn’t have the money. Multiple buildings worth of people were forced to share a single, outdated building during 5 year long renovations. Graduate students and University staff were criminally underpaid and underfunded. RAs were screwed out of salaries when the campus closed despite protections in their contracts. All in the name of budget shortages.

I overheard the Chancellor and the head of the Athletics department discussing an enormous, multimillion dollar training facility that was being commissioned on land that we were buying off campus. Our current training facilities are fairly new and our sports teams do not draw any crowds. We also bought an entire campus over a hundred miles away. F**k this place, and f**k the administration.

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.

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.

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.

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 d***s that day and he insisted he hadn't.

That was also one of the weirdest.

My uncle drove limousines for a while some years back. He had regular clients, like General Schwarzkopf. But one night he took a new client out. The guy asked my uncle to drive him to the bank and then take him home. When the guy called a second, third, forth, fifth time my uncle gladly drove him because he tipped really well. Then the cops showed up at my uncles house accusing him of being an accomplice to a bunch of recent local bank robberies. He somehow managed to convince the cops that he had no idea that the guy he was driving was robbing the banks, he just took him there and drove him home and got a nice tip. My uncle also had some amazing stories about being a truck driver for Budweiser, but I guess I should save that for a different sub.

Friend of mine drove for Nicolas Cage. The dude had a handler. If you wanted to talk you would have to talk to the handler who would then deliver the message to Mr. Cage. IN THE CAR.

Husband was a bit pissed that she spent 6k on a fur coat because they live in Texas. She responded kinda coyly "but we were on a glacier" He pointed out that she will never wear it again after that 20 minutes and she giggled like it was cute.

This was on a boat not a car. It was hot as s**t out and I despise the opulently rich.