Chauffeurs Who Drive Around Rich People, What Weird Stuff Did You Hear? | People Stories #505

chauffeurs who drive around rich people what are some of the weird shocking conversations you have overheard not a chauffeur but this happened because of a lack of one basically a guy i used to know back when we were teenagers 17 years old had a lot of money we just never knew how much until i was invited to go on holiday with him and some other friends all expenses paid of course anyway we took a taxi to an area where this guy wanted to buy an apartment and wanted to show us so we went with him and ended up spending the whole day walking around the area we got tired and eventually wanted to go back to the house but we were so far away that walking was not an option unless we wanted to walk for about three hours neither of us had enough cash to pay for a taxi and back then taxes didn't accept cards this was around 2000 or 2001 btw so this guy rings his dad and asks if he could send a chauffeur to pick us up but the chauffeur turns out was busy doing some deliveries for the dad so instead the dad says there's a mercedes-benz dealer shop near where you are i know the manager there is i've bought several cars from them just go there and buy there and buy a there and buy a there you can leave it in the house and we'll figure out how to bring it home later so we went to this dealer shop and somehow in about 30 minutes the manager did all the paperwork and we ended up driving back to the house in a brand new mercedes c-class which we used for the rest of the holiday frick billy bob thornton was doing radio press for a movie about to come out meaning he had to stop by six seven 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 it's a 250 cleaning fee if he smoked in the vehicle he asked to stop by a bank came out and handed me five thousand dollars cash and said here's for the whole god damn 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 picked up a wedding party bride brian's maid 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 c in the back they were using rolled up fifty dollars s and twenty dollars s 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 with a 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 but 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 i was a bouncer at a club in the 80s and only 18. i never knew see sex and tanning booths were so common it was like a pulp novel unfolding in front of me i was so naive when we were in high school my friend used a 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 p.m right off the bat the guy handed him 200 he went to her 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 freaked he came out and asked to be taken to the beach at this point it was like 2 3 am 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 sea like six months later i used to know a chauffeur he ended up driving around some big stars he was big dude like six feet eight inches 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 friend of mine worked for an upscale concentrate show for 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 carry-on 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 or 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 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 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 would 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 he got the happy ending not a conversation and not me but definitely weird shocking and disgusting a friend of mine who worked in music was in a limo with robin thicke and a load of dancers and models driving around london they are 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 holy crap i have a robin thick story too one of the administrative assistants at my work went to vegas and met robin thicke there he asked her at the bar if she wanted to come back to his room when she said sure he whipped out an nda to have her sign dude cheated on his wife so much that he had paperwork drawn up so the women couldn't tell on him 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 weed constantly and she was always worried she'd lose her job lol i used to drive limousine and taxi one time i got the manager of a fairly famous canadian band in my car asking me where to buy coke i had no idea where and i told him that so his bright idea was to find a prostitute hire her and ask her i told him i couldn't help him pick up prostitutes either he was disappointed but understood he had me drive down a well-known street until he saw a prostitute he asked me to pull over got out of the taxi pay the fare and then immediately flagged me down again as a new ride i knew what was up but whatever he gets back into the car with the prostitute and she tells him exactly what house to go to for some coke i take them there and wait a bit they come back out and i drive him back to the venue then he offers me two free tickets to the show which i gladly accepted as love that band and had seen them three 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. 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 two prostitutes blowing him out of all of the answers this is the one that made me go yep that sounds about right freaking blackpool i've have multiple people pay me handsomely to let them smoke weed in the car heard a french guy yelling at his wife at ten thousand dollars was too much to pay for two bracelets that she bought also overheard a lot business deals with absurd amount of money referenced like tens of millions i've had conversations at work where i've said just by the two other dang things it's only 25 k kind of crazy to from that to debating if i wanting to keep my hbo subscription that night drove limo 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 a couple things i remember randomly from it one drunk guy leaves his wallet on a van and another driver calls it and 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 okay two i picked up a couple girls from akaio 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 dollars a month the school is in milwaukee wisconsin three mardi gras is the name of a campus ministry trip where you use your spring break to build houses and drink and 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 if i recall correctly four 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 an em at five it is a free service and a frat star tried to pay me for the ride with a ziploc baggie of c i said no and he called me a legend and left the twenty dollar in the cuff holder before i realized it this is not a limo story but this thread reminded me of a rich guy story my daughter played soccer for many years and at one practice a guy drove up in a ferrari got out and started talking to another of the dads on the team after a few minutes the guy left and another of the dads went over there and asked him who that guy was he replied that the guy was his lawyer or something i come to find out years later that that guy in the ferrari was a multi-millionaire had one and only one client that dad and his only job was to handle the dad's charitable donations so this dude got filthy rich donating millions of dollars of somebody else's money and taking a percentage off the top the dad who was apparently worth several hundred million dollars never came across as rich at all he wore sweats to and was at every practice and game he drove a camry had been married to his average looking wife for like 25 years stuff like that acted like a normal guy like the rest of us 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 her pet a demonstration i'd rather be bare than infer 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 i remember that the girl from walking dead was in that shoot not a chauffeur it seemed like a good chance to remind people of the story of john boner at the time speaker of the us house of representatives third in line for the u.s 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 uberpool that's what he used for years there are all sorts of tales of commuters hopping into their carpool and bam there's jon boner 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 one of my best friends used to drive uber in a wealthy area of l.a he told me so many stories about drunk celebs and tick tockers in his car someone offered him a bag of weed because they felt sorry for their friend throwing up in the back seat most people were just normal though some highlights quentin tarantino and trisha paytas were making out in his backseat when they were secretly dating lol mike tyson is apparently very nice in person and also a giant pothead 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 addison ray or one of her friends took their shoes off and left them in the car leo dicaprio took more than five minutes to find the car he seemed out of it and was quietly bobbing his head listening to music on his headphones wasnt exactly a chauffeur but i did have the distinguished privilege of working with a multi-millionaire 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 alright when i told him i couldn't afford to go yet and had to save up having a scottish castle moved to the u.s and reassembled here is literally the plot of gargoyles a 90s cartoon on the wb i'm kinda excited to see where this goes not a chauffeur and i was a participant in this conversation i used to tutor an oligarch's daughter in rebelevca the wealthy suburb outside moscow and 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 the cross country is quite popular in russia it's even part of some school's 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 i was definitely expecting something much different 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 owners handlers was training a new flight crew he ordered 12 k 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 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 not a chauffeur a small part of my family was chicago mafia grandpa told me a story of a famicy wedding in chicago they went to in the late 60s 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 eight times by various police officers the officer would walk up to the driver's window the chauffeur 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 it's thursday that's when we pay our boys so i guess that's how they did it looks like a traffic stop and in the open where it's not unexpected so i'd imagine that joffer had seen some things 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 imagine hiring a limo and sitting in the front in australia we tend to sit in the front in taxes so it could have been a bit of that too 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 as 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 i used to work in politics and never heard a bad thing about house and romney acts in his personal life seems genuinely courteous and respectful to people i have deep ideological differences with him but you can tell an elected's real character in how they treat underlings i sometimes uber drove in dc and they would order a ride but instead of getting in the vehicles they would just put a bunch of paperwork in your car and then you would deliver it to the next government building always felt kinda sketchy that government employees would send documents via uber drivers lol i was driving as uber and i picked up two businessmen 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 u.s 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 4 000 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 maximum 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 and roses like they were the grateful dead he thought axel 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 drugs that day and he insisted he hadn't that was also one of the weirdest it sounds like a guy having a severe manic episode i am late to the party but i can absolutely contribute to this thread used to work for a private transportation company started my own show for business last year a couple things right off the top of my head that come to mind one had a really snobby family from another mountain estate come to our state and the entire ride to their destination was spent talking about how much better their state was towards the end of the ride the mother started cutting her toenails in the company vehicle no idea how to react to that situation basically just had to let it right two probably one of the wealthiest people i've ever met in my life was a gentleman who was a very high ranking member of scientology was also one of bill gates close business partners never in my life have i been treated like i did not exist until that right barely even got his name before he asked not to speak for the almost two hour ride three just previously i drove an nfl all-star and he was one of the coolest people i've ever met which was super refreshing all i ever heard of celebrities particularly athletes was that they could be very rude guy was just a regular but homie who gets paid 15 mil a year scientology guy sound sus af if you are new to the channel you can subscribe i publish new videos every day until then check another video [Music] bye for now

Channel: Updoot Studios

Views: 36,419

Rating: 4.8990917 out of 5

Keywords: chauffeur, chauffeur service, rich people chauffeur, driving rich people, designated driver, #updootst, updoot, updoot reddit, updoot everything, reddit on tap, toadfilms, pewdiepie, reddit, askreddit, funny reddit, reddit stories, top posts, reddit top posts, reddit cringe, comedy, reddit compilation, /r, r/, r/askreddit, top posts of r/, askreddit reading, best reddit posts, top posts of all time, people of reddit, askreddit question, ask reddit, subreddit, sub, reddit stories 2021

Id: CIyk4wf0h9g

Length: 24min 11sec (1451 seconds)

Published: Sun May 16 2021