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.

letsryan

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

Puddle_Boots

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 f*****, 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

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.

MastadonBob

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 pr******te, hire her and ask her. I told him I couldn't help him pick up pr******te either. He was disappointed but understood. He had me drive down a well known street until he saw a pr******te. 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 pr******te 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 I 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

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

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

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....

pursuitoffruit

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 pr******tes bl**ing him.

mattmu13

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.

close_thelid_grillme

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.

prailock

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

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

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.

close_thelid_grillme

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...

GoFox_97

It is a free service and a frat star tried to "pay me" for the ride with a ziplock baggie of cocaine. I said no and he called me a legend and left a $20 in the cupholder before I realized it.

prailock

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.

whoreychan

I 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.

close_thelid_grillme

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 meth?"

prailock

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.

Proper-Beach8368

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

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.

prailock

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

mcgato

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**ual 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.

throwawaylogin2099

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.

prailock