Have you ever wondered what secrets are concealed behind the tinted windows of luxury vehicles? Chauffeurs, the silent observers of high-profile individuals, hold a treasure trove of intriguing tales about their clients. From the glitz and glamor of celebrities to the mysteries surrounding influential figures, these drivers have witnessed it all.
1. Smoking Habits
“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,” one person shared.
2. Wild Bridal Party
“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 “stuff.”
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 did their thing, 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,” another person shared.
3. Losing 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,” one person recalled.
4. The Happy Ending
“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 “special” massage places. 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 massage haha!”
5. The Band Manager
“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 [the goods]. I had no idea where and I told him that, so his bright idea was to find “someone on the street”, hire her and ask her. I told him I couldn’t help him pick them up either. He was disappointed but understood. He had me drive down a well known street until he saw one.
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 girl and she tells him exactly what house to go to for some stuff. 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,” one person shared.
6. Backseat Celebrity Secrets
“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 the green stuff because they felt sorry for their friend throwing up in the back seat. Most people were just normal though.
Some highlights:
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Quentin Tarantino and Trisha Paytas were making out in his back seat when they were secretly dating lol
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Mike Tyson is apparently very nice in person
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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
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Addison Rae or one of her friends took their shoes off and left them in the car
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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,” someone shared.
7. The Out Of Touch Multimillionaire
“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,” one guy recalled.
8. Backseat Private Jet Sale
“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,” one person shared.
9. Backseat Mafia Dealings
“Not a chauffer. 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. They were picked up at the airport by a limo with some high ranking family members. On the way to the hotel they were stopped about 8 times by various police officers. The officer would walk up to the drivers window. The chauffer would reach into a money bag and pass a bill to the officer. Nothing would be said and they’d take off again.
Eventually my grandpa asked if they were being bribed. His cousin (mafia) laughed and said, ‘No its Thursday. Thats when we pay our boys.’ So I guess thats how they did it. Looks like a traffic stop and in the open where its not unexpected. So I’d imagine that chauffer had seen some things,” one guy shared.
10. Meeting Mitt Romney
Not a driver, but I used to caddy at a fairly exclusive country club in Massachusetts. It’s the kind of place where, no matter how rich you are, you can’t buy a membership. You’re either born into it or you marry a member. As a result, a lot of the members like to show off their influence by inviting guests who would otherwise be unable to play at the club.
Someone invited Mitt Romney. We were given a heads up that the governor (he wasn’t a senator yet) would be coming and they wanted us to know how to act around him. We were told he wanted to be treated like anyone else but they didn’t want us to gawk. So, I guess to make sure us dumb caddies weren’t gawking, we were instructed to not look at or acknowledge the governor.
Because this is precisely how we would treat other people. I did get to shake his hand and chat a little bit. He was friendly, personable, way nicer than a lot of the members. I still don’t like a lot of his politics but he seemed nice enough in person,” one person recalled.
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