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Driving people around is no easy business. They come with all sorts of personalities, emotions, and expectations, bringing together not just their baggage, but also a certain degree of unpredictability. However, when dealing with the rich, who are known for their extravagant behavior, the chance for unexpected situations increases even more. So, Reddit user Cicallis made a post on the platform, inviting chauffeurs who have experienced something like this to share their stories. Below, you will find the most memorable ones!

#1

"Driving through a city tunnel, capturing a driver's perspective with rich people stories in the background." 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 , stephen packwood/Unsplash (not the actual photo) Report

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    #2

    Airplane flying over clouds and ocean, seen from above, capturing travel and luxury. 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 , Alexander Mils/Unsplash (not the actual photo) Report

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    Bernd Herbert
    Community Member
    9 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Well-off people are not an issue per se. Rich people, who are THAT far from reality are. I really detest those f*****s.

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    #3

    "Driver with sunglasses in a car, possibly listening to rich people's stories while on the road." 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.”.

    Altitude528O , Chethan KVS/Unsplash (not the actual photo) Report

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    #4

    A driver listens intently while driving at night, city lights visible through the car window. 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.

    mrw4787 , Getty Images/Unsplash (not the actual photo) Report

    #5

    Smiling driver holding a phone, possibly sharing stories about rich people while behind the wheel. 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.

    anon , Getty Images/Unsplash (not the actual photo) Report

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    #6

    "Driver's view inside car with GPS, navigating city streets while driving for wealthy clients." 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.

    anon , Clay Banks/Unsplash (not the actual photo) Report

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    Chuck
    Community Member
    7 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    The last time I spent $30M in 10 minutes, well, the check bounced. I don't have $30M.

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    #7

    Guests in a limousine raising champagne glasses, celebrating, reflecting on stories about rich people. 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.

    Proper-Beach8368 , Michael Benz/Unsplash (not the actual photo) Report

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    #8

    Car in a dimly lit alley with reflections on wet pavement, capturing a mysterious ambiance about driving rich people. 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.

    PrometheusAborted , David Lee/Unsplash (not the actual photo) Report

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    #9

    Driver in a car, focused on the road, possibly hearing stories about rich people while working. 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...

    anon , Viktor Bystrov/Unsplash (not the actual photo) Report

    #10

    Woman applying makeup in car, seated behind the driver, embodying stories from drivers about rich people. 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.

    zbubblez , Getty Images/Unsplash (not the actual photo) Report

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    #11

    Two people sitting on a boat, viewed through a cabin window, enjoying a scenic ride, evoking stories of rich people. 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.

    whateverrughe , EVREN AYDIN/Unsplash (not the actual photo) Report

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    Family's_disappointment
    Community Member
    11 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Honestly no offense but spending a lot of money on things that you are actually gonna use is far better than spending money on stupid things that you're never even gonna look at again

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    #12

    Uber sign glowing on a car window, highlighting stories heard by drivers about rich people. 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.

    kry1212 , Erik Mclean/Unsplash (not the actual photo) Report

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    #13

    Driver in a car, looking thoughtful, with hands on the steering wheel, hearing stories about rich people. 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 , Getty Images/Unsplash (not the actual photo) Report

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    cerinamroth
    Community Member
    10 minutes ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Most castles in Scotland would be protected by the National Trust or other organisations to protect Scottish heritage.

    #14

    Driver in an Audi, navigating city traffic; overhearing stories about rich people, with a GPS on the dashboard. I’ve have multiple people pay me handsomely to let them smoke w**d 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 , Thibault Penin/Unsplash (not the actual photo) Report

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    #15

    White limousine parked on a suburban street, symbolizing luxury transportation involving rich people. 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.

    throwawaylogin2099 , Richard R/Unsplash (not the actual photo) Report

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    Bat cat in a hat
    Community Member
    7 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    That's what baffles me most, how those mega rich people simply blank out the "help"

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    #16

    Driver in a car on the highway, smartphone with a map app mounted on the dashboard, rich people stories in mind. 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.

    hotpocketsinitiative , Paul Hanaoka/Unsplash (not the actual photo) Report

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    #17

    Man in denim jacket leaning on a railing, outdoor setting, rich people rumors hearable in taxi rides. 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.

    mutantandproud95 , Walt Disney Studios Motion Pictures Report

    #18

    "Driver on a rainy day, navigating while listening to stories about rich people." 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.

    anon , Tom Morbey/Unsplash (not the actual photo) Report

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    #19

    A smiling driver in a white van, possibly hearing stories about wealthy passengers while on duty. 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 , frank mckenna/Unsplash (not the actual photo) Report

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    #20

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

    Current_Elk_550 , Getty Images/Unsplash (not the actual photo) Report

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    #21

    A woman with bangs in a colorful striped top, sitting in a dimly lit room, related to stories about rich people. Not a chauffeur but I worked as a busboy for a very rich country club. I know it cost at least a couple hundred thousand for continuing membership fees. I constantly had to be going from table to table while the rich people were dining and I would overheat snippets of conversation. Heard one group of younger adult men talk about how they broke into the basement of one of Taylor swifts homes.

    shelfshelf , Taylor Swift/Youtube Report

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    #22

    Driver in a city car, capturing stories about wealthy individuals, with urban buildings visible through the windows. I drove 2 big time movie directors once. It was about a 30 minute drive to their jet. They were talking about all the gay guys in Hollywood. The ones that they both emphatically agreed on were John Travolta and Jamie Foxx.

    I also drove Stuart Scott once. He sang happy birthday on the phone to one of his daughters months before he passed away.

    anon , Xingchen Yan/Unsplash (not the actual photo) Report

    #23

    A woman with long brown hair, wearing earrings, in a studio setting, related to rich people stories from drivers. 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 , Katie Couric/Youtube Report

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    #24

    Man driving a luxury car, looking focused, symbolizing the experience of hearing stories about wealthy individuals. I was a driver/bodyguard for a OG rich Chinese guy who came to Canada in the 90s.

    - during a drunken drive home he told me his birth story... his mom was an artist and one of the top officials in the CCP had an affair and impregnated her. Magically she had papers to immigrate to any nation she desired.

    - he and another rich Chinese friend planned to steal the money his dad was going to give him to pay for his four year college program, move to the city the school he was "accepted" to and trade penny stocks and find a virgin [escort]. It was the first time I got double shock.

    - one of the last major conversations I have working for him was how dark skinned people are scary, so it's not racist, that Chinese people as a whole view it like that and no sensitivity/racism training would explain it well enough to make Chinese people as a whole change their mind. I asked him how it was that he hired me, other then being scary...
    two weeks later he replaced me with two big white guys.

    br0wnb0y , Getty Images/Unsplash (not the actual photo) Report

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    #25

    Driver in a car at sunset, experiencing stories about rich people while driving. I had a job as a runner. I would pick up music artists from the airport and drive them to the venue, among other things. I won't name the artists, but I picked up one duo from the airport in an Escalade. It was raining heavy that day and I had the windshield wipers on next to full. It created a beat. One of the guys has a small, hand held sampler and starts making beats in time with the windshield wipers. All of us were driving along, bouncing to the rhythms. It was sweet. Another time, I was driving a famous songwriter/guitarist back to the airport after the gig with his family in a 15 seater van. His family was telling him how great he was, but dude is old. All he could say was, "What?" and "Huh?" It dawned on my he couldn't hear. Bob "Percy" Plant can't hear s**t. I have a ton of other stories, including how I got involved, but I'm not sure if anyone wants to hear them.

    robo-tronic , Getty Images/Unsplash (not the actual photo) Report

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    #26

    Driver in a car, focused and thoughtful, as he hears stories about rich people. I was an Uber driver in Boston for awhile.
    I had accepted a Pool trip near Southie and picked up my first passenger, a Spanish speaking woman with broken English. My next stop was at T bus barn. I’ve picked up bus drivers before and that’s where the pickup location showed on my app. Upon arriving, I waited for a minute or so and got a call. It was the woman I was supposed to pick up.
    “Where ARE you?! Why are you stopped and not HERE WHERE I AM?!”
    I asked what her location was and she screamed something about being across from a Starbucks. So I googled the nearest Starbucks and drove there. I was already close. I stopped directly across from the Starbucks and saw no one. So I called her.
    Lady: “WHERE ARE YOU?!”
    Me: “I’m across from the Starbucks... I don’t see you.”
    Lady: “I’m right F*****G THERE!!! WHERE ARE YOU?!”
    “Me: Miss I think you need to find another driver.” And I canceled her trip.
    All of a sudden, from the sidewalk bus waiting shelter, emerges this angry woman screaming and shouting “IM RIGHT HERE... “IM RIGHT F*****G HERE!!!”
    I take off and book it... running a red light to boot. (It was like 3AM)
    The Spanish lady in the back said “I’m v-very h-happy she didn’t make it inside”
    I laughed and the trip finished peacefully.

    anon , Getty Images/Unsplash (not the actual photo) Report

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    #27

    Man in a suit talking on the phone inside a car, possibly discussing rich people stories while driving. Our temporary chauffeur when the main guy was on vacation thought my dad’s mistress’s son was my brother.

    Pretty awkward when he asked my mom, a mother of only girls, about her son that he had just dropped off with “his father”...

    Wit-wat-4 , Getty Images/Unsplash (not the actual photo) Report

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    Deborah
    Community Member
    7 hours ago

    This comment is hidden. Click here to view.

    Temporary chauffeur? And you think this belongs here? You're on the other side of this fence, dude.

    #28

    Luxurious white limousine parked on a city street, highlighting transport for rich people. 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.

    Mysticalmayo , VENUS MAJOR/Unsplash (not the actual photo) Report

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    #29

    Driver in a car with sunset view, hearing gossip about wealthy passengers. 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 , why kei/Unsplash (not the actual photo) Report

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    #30

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

    satanismymaster , Senator Mitt Romney/Youtube (not the actual photo) Report

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    #31

    This happened to my roommate , been years ago . Living in NY . He worked part time as a chauffeur. He was all ways picking up rich people. One night his boss told him to pick up LT Lawrence Taylor of the Giants . He was going to a party up town. So he picks him up . Very nice to him . Had two other guys with him . He takes him to this party going on . Limousines parked all over . LT gets out and says wait on me . So he waited for like 2 maybe 3 hours . LT comes out and says “ I’m sorry to keep you waiting, but I’m going to catch a ride with friends. I apologize. Hands him 500 dollars cash .

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    #32

    Airplane taking off under clear skies, representing travel experiences of rich people. 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.

    nanocurious , Alexander Mils/Unsplash (not the actual photo) Report

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    #33

    Drove a few celebrity athletes to signings and stuff but the craziest things were what the quiet billionaires who had $10M summer homes in my area would talk about. Nothing depraved or dangerous. Quite the opposite, really. The mundanity of life with a security that few can fathom.

    One guy, I would pick up in Manhattan twice a week and drive him home to his summer house. Gigantic. I live in a 4bed, 2.5bath with finished basement. It would fit in his pool house. One drive he's laughing with his business partner about a phone call he had on speaker. A major retailer was trying to back out of a deal because the merch was not making it on time. He talked around it, sending them news articles about slow shipping due to emergency tariffs and War on Terror blockades. It was like someone trying to sell you the extended warranty but he kept the deal. The next week, he's s******g bricks because we're stuck in traffic with nowhere to go and he's going to be late to a fundraiser his wife started for his kid's school. He made a big box store fold like a cheap suit but "unhappy wife, unhappy life."

    Another was an older lady who was the community gossip. She was going on and on, telling the stories of these prominent families who all belonged to the same house of worship. One was pretty well known and influential but, as she would tell it, flat broke. The rest of their community could not let it seem that way and buoyed them up. They kept living in mansions and driving high end imports and getting added to business deals as a tertiary partner to replenish the fortune like rain gathering in a bucket.

    One of my favorites was a guy who probably wasn't a billionaire but he was in the nine figure range easy. He always had great cars and tipped well but explained that all his cars were bought off lease. Someone else paid too much to drive it for two years and now he pays for a top end car but for a reasonable price. Any time he wasn't headed to his office or to get smashed at his country club, he was in jeans and a polo or a concert T-shirt. When his father-in-law died, a nice old man that we often drove to medical appointments, he texted each of the drivers from the service to thank us for driving him and having conversations with him as he always had a good time and brought our stories back with him (most of us active or retired military or LEOs.)

    People who could buy a country if they wanted but really just people in the end.

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    #34

    Im not sure if i qualify, but i was chauffeur of this one bank/incurance companys CEO, for one summer. I found out, that he and lots of his married friends were cheating on their wifes, did some lowkey frauds, and were f*****g arrogant against "normal" 9-17 working class. And top of that all that we didnt have any non-disclosure agreement, and he paid me cash, off records, and still do own me approx. 500€. I have thinked that, if that c**t dosnt pay me, i will talk to media, and that 500€ will cost that prick, his whole career, and reputation.

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    #35

    Finally see an AskReddit that pertains specifically to me and it’s already 2.5k comments deep 🤦🏼‍♂️

    Generally just anything involving disregarding the fact that you’re a human with ears. I’ve heard all sorts of confidential business discussions that are sure to make major waves, probably classified information, and all SORTS of graphic sexual discussions

    1)

    “he got a kilo for his birthday?”
    “Yeah, that’s why he’s flying private [to ibiza]”
    “Like he wouldn’t anyways”
    “True. Him and his f*****g jets”

    2)


    “you know he’s Ex-CIA right?”
    “Yeah, but they don’t like...let you keep s**t, right?”
    “I don’t know. When you’re that high up, probably. He’s got like half a mil tied up in guns alone. You should see the armory at his place in Texas”


    Bonus trivia: the richer the client, the s***tier the phone. I’m perpetually astounded how universally true this is. Trust fund babies, mid-low tier celebrities, musicians, athletes, d**g dealers, the $500k-10m club: all the latest iPhone in designer cases. CEOs, presidents, “board members”, Illuminati types, the $50m+ club: still all rockin iPhone 6, 7, and 8 or older androids. Client today owned one of the largest energy companies in the US, iPhone 6 with a cracked screen.

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    #36

    I'm pretty sure my confidentiality agreement has expired by now but I used to drive around a Hollywood Director that requested a Rabbi, a Priest and a Tibetan Monk accompany him to his meeting with the Studio execs in an attempt to salvage his cut of the film. I'm sure it made the trade magazines at some point, but not a widely known story.

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    #37

    I met a limo driver in Atlanta with some of the best stories. He was a driver for years and had driven politicians,, rappers lottery winners, d**g dealers the whole gambit of the human condition that would call for him for a ride.

    The company I work for had a contract with the company he worked for so he would drive me to the office once every 6 months for like 3 years.

    **Highlights**

    **Rich old white lady**

    - She hired the company to driver her to New York. The catch was she wanted to detour through Knoxville so she could stop at every single Cracker Barrel along the route. She chose the route with the most Cracker Barrels. To quote him "Its Cracker Barrel they are all the same. She wanted to stop at Every...single...one" The trip was supposed to take 2 days and ended up taking 4 because of Cracker Barrel.


    **Lottery winner or thief**

    - He didn't know why this guy had money but he got a call to a s****y neighborhood. He was nervous driving a limo in the slums of Atlanta. He picks the guy up and he is struggling with this wad of cash.

    The guy asks the limo driver if he knows where he can get [illegal substance]. To quote the limo driver "I'm a limo driver, of course I know where to get [illegal substance]" So he goes to the spot grabs this guy an 8ball and gives it to him.

    The guy asks the driver if he knows where he can get an [escort]. Again to quote the driver "Im a limo driver, of course I know where to get some girls."

    So the guy has a pile of [illegal substance] and a blonde chick in the back of the limo. The driver says it's strange because this guy is swinging way outside his weight class. The [escort] thinks its Christmas and is hogging the [illegal substance].

    So the guy finally gets the bag away from her and dumps it on the table in the back and is about to rail a line when the [escort] pops the sunroof on the freeway. The wind blows the [illegal substance] around the inside of the limo like a tornado. At this point in the story, the driver is cracking up and says "The [escort] was frantic and tried to snort the dust out of the carpet. Ah hahaha". I am cracking up he is cracking up. I thought he was going to crash just telling me the story.

    He says the guy asked him to get him some more but he had to call someone else to his hotel because in his words "You don't buy an 8ball and then show up an hour later for another without questions"

    **The politician**

    - So this driver gets a job for a woman. They drive around a bunch of mostly business-type buildings corporate s**t. His company does a lot of business with corporate headquarters and staff. She finishes and asks him to go to one last place where they pick up some random guy. He drops them off at a hotel and leaves. He picks them up the next day and takes them to the airport.

    Fast forward to the next week and the company calls him asking what happened. He is confused. They say a lot of reporters and s**t were asking questions about what happened with his passenger. He didn't know what was happening. Then the company gets contacted by the FBI and some investigators.

    At this point, he is spooked and bails. Stays home avoids work. His friend at the company gives him the number of an agent that wants to question him. The funny part is this guy is black but his name is Hispanic. He thinks he is safe as long as he stays in his black neighborhood. He thinks they are after him for the guns he carries or something.
    He goes to a phone outside his neighborhood and calls the agent. The agent asks him about every stop and every person the lady he drove stopped or met. They get descriptions and then let him go.

    Turns out the guy was a married politician banging a corperate executive. Huge scandal ensues.


    This could have all been b******t but I loved seeing that guy because for a couple of hours a year we would sit in a car and shoot the s**t and have a great time.

    anon Report

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    #38

    Back in the 2002 Winter Olympics I volunteered to be a driver at the Olympic village. I got assigned to drive a very famous rapper (if I said his name, 100% of the people reading this would know his name) and his friends from the village to the huge mansion they rented to stay in. They were assigned a ‘concierge’ by the SLC Olympic committee to make sure they knew how to get around, where to eat, and whatever else was needed while they were in town. Well for the whole hour long drive this rapper and his friends openly sexually harassed this poor lady who was sitting up front with me. They each felt that they needed to explain to her every dirty thing they were going to do to her that night.

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    #39

    Chauffeuring family count?

    A relative of mine flew in from overseas, spitting mad. Apparently he’d lost a military contract, War Dogs-style, to some schmucks who “didn’t know s**t even if it came outta their a*****e” (his words), and the gov’t had given the contract to my relative on the plane flight home...and hadn’t changed the due date. He had two days to meet all the demands. On the drive home he was angrily trying to order a satellite to fly over a certain country, so that some general or something could have wifi ASAP. I didn’t realize you could just “order” satellites like one of those messenger planes you see on the beach.

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    #40

    Drove L.I.M.O. at Marquette University during undergrad and grad school. Some of the students that went there were obscenely wealthy. Limos are the vans that drive drunk students anywhere on campus and a few blocks outside of campus. Couple things I remember randomly from it:

    1. 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.

    2. 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.

    3. 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.

    4. 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?"

    5. 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 Report

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    #41

    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.

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    #42

    Not rich or famous, but I drove Lyft for a few months. I picked up a group of 5 bankers from their holiday party, each wanting to be dropped of individually but promised to “make it worth my while.”

    Tip was $2.

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    #43

    Drove taxi in upstate NY (nowhere near nyc). Had a couple douche rich guys who would try to give me shots of liquor while I was driving. I declined of course. Best one I had was a regular who happened to be a very expensive escort. She always requested me, I guess she felt comfortable since I'm a large guy and very quiet and discreet. Anyways she used to give me a hundred dollar tip every time I picked her up. I don't think I've ever said more than a couple words to her and I drove her once or twice a week for over a year.

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    #44

    My brother drove important people and top models to and from fashion shows and galas for some time, years ago.

    Among the many weird people he had to deal with, there are two that he told us because the stories are ludicrous.


    1. He got a model to take for a photo shoot but the guy would not stop moving on the seat all the trip. It was summer, so my brother asked if he was feeling hot and would want the AC to be set lower. The guy did not answer, was moody and snob about it. Until he received a call, and the person on the other side was his bf. Since those cars were top of the line models, you can hear the entire conversation. All normal until then, when the guy sitting on the backseat suddenly accuses his bf from his bleeding for the entire morning and have to wear diapers to the photo shoot.

    2. Was driving a well known person from a fashion show to her hotel to stay the night before the flight on the next morning. As a prestige driver, the less you speak the better, until this mid-aged lady asked him where were the bars open at night. Cordially, my brother explained that it was around 2 kms away from her hotel, to what she replies that she wants him to take her there. Until then, all good. Then he would have to wait for her, taking into account that the trip is only finish when she reaches the hotel, he was to be there for her. Things get a big twist when she arrives at the car with 3 young ladies and asks my brother to take them to a different hotel room, Puzzled, but complying with her wishes, he suggests a hotel that is around 5 kms away from the 5 stars hotel that she is staying. All good until then, when she requires him to find her certain items to play at that late hour of the night (2 am). Unable to find anything open, he suggests her to improvise. Left them on the side of the hotel, and went to rest. Next morning, since the VIP service include everything, he is suppose to pick her up to take her to the airport. But her phone call was surprising, when he had to go pick her up around 36 kms away from the place he left them, on a shady and weird hotel.
    All good for him, until she enters the car and he realizes that she is trying to tangle what he thought were strings inside plastic boxes and smelling them. Only to come to realize it was hair. In a relaxing mood, asked her how was the night, to what she responds that she enjoyed it quite much, since they were beautiful young women, and brags about it, until the point he asks her about the necessaire. Her response was, I take as souvenir a piece of hair from every woman I sleep with.

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    #45

    Just had to share this. A coworker of mine was telling how on his side gig as an uber driver, he had picked up one of the receivers for our local NFL team. He complained that he had driven this man for a half hour and didn't even get a tip or a good rating. "That a*****e just signed a six million dollar contract and he couldn't even tip me"! Then he added how he trash talked the NFL guys abilities during the whole ride.

    Sometimes like gives us reasons to smile!

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    #46

    Luxurious car interior featuring a sleek dashboard and steering wheel. I drove the Canadian Cabinet Minister of Health to a Blind or meeting, and they had an "aide" (pre web) that briefed them in detail for 'this meeting',it was a bit off putting.
    In contrast Hose Feliciano was funny as hell and had a beautiful girlfriend.

    Northviewguy , Brock Wegner/Unsplash (not the actual photo) Report

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