What was that saying about humility? That some people have it and that some don’t? Well, that’s probably the one saying we can count on in the world today. And as unfortunate as it can be, sometimes it’s pretty entertaining how proud and privileged some people act, especially because they have money.
And that’s why we’re here today. We’ve gathered some of the funniest, most confusing and downright horrible stories about rich people you’ll ever read about. A lot of these people have gotten their just desserts, some remain clueless and others just throw money around like they have a grove of trees. Either way, they’re all tales that we can laugh at. If you’d like to read about some dumb things that people with money have done, just scroll down.
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39. Screw the Rules, I Have Money
Local billionaire, Paul Allen, wanted to put a helicopter landing pad at his waterfront compound on Mercer Island several years ago, but the city said no.
So, Paul Allen had a custom made helicopter landing pad ship built, that motors out 100 yards into the lake, beyond the city’s jurisdiction. Whenever he wants to take off or land via helicopter, he just does it on his pad. Zoning regulations are for normal people.
38. She Can Easily Afford a New One
I was pumping gas in a rather dicey neighborhood at a cheap gas station and this older woman pulls up in her Bentley. She pulls up on the pump ahead of me and cracks her window slightly and asks me for help. I ask her what she needed. She asked me to pump her gas cause she was too scared to do it herself, so I asked her what type of gas she wanted and she said the cheapest.
When I asked her if she was sure, (because such a high-end car shouldn’t have budget gas), she said it didn’t matter since she could easily afford any new car she wanted. So I insert my debit card and she hands me a $100 bill and says keep the change. I filled up her tank and my own (a 12-gallon Honda Civic tank) and made about $30 from the change.
37. Disneyland Is Now Boringland
When I was in high school, my family was pretty poor and I had a fairly rich friend. My single dad spent years saving up for us to go to Disneyland and we finally went when I was 16. Fast forward a year and my friend is going to Disneyland for Halloween break. Her dad told her to invite two friends, so she invited another girl and me. I was freaking stoked, but she kept saying “I don’t know, but this trip is probably going to be boring; my grandma takes me to Disneyland like every break.”
When we got there, all she wanted to do was sit on benches and text. All of the rides were “boring,” and she’d already been on them dozens of times. It ended up being pretty boring for me because I didn’t want to go on the rides without her.
36. $3 Million Just to See The Lake
My old boss bought a three million dollar lake house, but there was a house between his and the lake shore.
Apparently, his wife wasn’t happy about not being able to see the lake, so he bought the other three-million-dollar house and had it torn down so his wife could see the lake. That’s the kind of life choices people get to make when their annual income is in the tens of millions.
35. A Million Dollars Wouldn’t Make A Difference
Back in high school, we were doing one of those ice breakers where we passed a beach ball around and whoever caught it had to answer the question their thumb landed on.
Well, this kid who proclaimed he was rich numerous times and often talked about his parents owning a known pizza place and the fact that he drove an expensive sports car caught the ball and his question was “If you won a million dollars what would you do with it?” His response was somewhere along the lines of “A million dollars wouldn’t make any difference in my life.”
34. Rich But Lonely
I knew someone who traded in his Porsche and bought a new one every year. His parents were wealthy but died when he was in his teens and left him a multi-million dollar trust fund.
What was sad was that he felt that he couldn’t pick up women without flashing his cash and expensive sports car, but he would dump them all in a couple of weeks because “they were only into me for my money.” He was the loneliest guy I ever met.
33. The Richest Pizza Guy Ever
I deliver pizza in a VERY rich area. I’m talking seeing Rolls Royce’s and supercars on a daily basis kind of rich. My manager told me a story about someone who used to work there. This guy would deliver pizzas in a brand new BMW M3 and just put absolutely no effort into his job (delivering pizza isn’t hard).
Apparently, the guy only had a job because his parents wouldn’t pay his allowance if he didn’t work. How much was his allowance? $5,000 a month. This guy was making $60,000 a year to deliver pizza part-time. It was crazy.
32. “I Only Drink Water from France”
I’ve been a flight attendant for ten years and one of the craziest passengers I’ve ever had was when I asked this lady what would she like to drink. She said, “I’ll have a water.”
When I was about to get the water, she said, “Wait, where is your water from?” I was confused, so I asked her, “Uh… What?” Well, her response was, “What country is your water from? Because I only drink water from France.”
31. $28,000 For A Pallet of Water
There was a superyacht docked in Italy at a high-end marina. The owners wanted bottled Perrier water for a party they were having in a day or two. They wanted the marina to supply them with a pallet of said water. But the marina said it was against policy for them to get a pallet of water to their boat.
So they got a private jet from America to fly in a pallet of said water and got it dropped to the boat. The price was about $28,000 USD if I remember.
30. Break to Upgrade
I had friends who “had to break their phone.” It was the latest iPhone model and was working perfectly, but there was a newer one coming out that they wanted and their parents would only buy it if their other one was broken.
I had to endure these kids throwing their phones against walls and being frustrated that their phone wasn’t broken yet.
29. Submarine For Valuable Art Pieces
I live next to one of the greatest wealth per capita places in the world. A guy over on the island had the problem of his priceless art in his winter home being in danger from potential hurricanes, and he wasn’t comfortable with the idea of it being moved out of the house when a hurricane was coming.
His solution was to buy a decommissioned submarine and have it buried underneath his estate. He then had a hallway built leading to it and that’s where he puts his most valuable art pieces at that particular home of his.
28. No ‘Crappy’ Cars Allowed
My rich aunt doesn’t let us park in front of her house because it makes her mansion look bad. She’s married with four kids, her husband is a Hollywood producer (hence the mansion) and she hasn’t worked a day in her life.
Since she lives far away from us, whenever we go there, I have to rent a car. Mind you, my car has never been something that was unappealing. It was a clean, relatively new Audi model. It’s just strange.
27. Every Day is Bank Day
I work at a local bank. We have several employees who only serve the richest of our customers. They come in almost every day to take out $20,000 in cash and some days just to check their balances. I think they just like us telling them they’re rich.
They will call up and just start telling us what they want when they get here in 5 minutes, not even saying hello. If we don’t answer within the first ring, a few of those customers start yelling at someone. Thankfully, there is a private number they call and it rings differently.
26. The Rolex or the Cartier?
I was invited to a graduation party, hosted by a very wealthy couple whose daughter had just graduated from Yale.
Her father came out, in front of the guests, displaying his Rolex and Cartier watches, asking which one of the two expensive watches the group thought would be “more appropriate for the occasion.” Everyone just looked at each other, silently, not quite sure what to say.
25. The Golf Club Fanatic
I went to college with a totally chill dude who was apparently rich as hell. He was on our college golf team and enjoyed destroying a club if he hit a bad shot. He wasn’t even angry; it was just like a reflex to go Bo Jackson over his knee or whatever.
I asked him how he keeps playing by wasting all the equipment and he basically said that at the end of every round he just bought new clubs for the next round. He showed me in the trunk of his car that he had about five boxes of irons and always took the plastic off a new driver for each round I saw him play (and he played every day at least 18 if not 36 holes). He said it wasn’t even a rounding error in his dad’s credit card.
24. The Difference in His Bank Account
A consulting manager I worked with was literally Stiffler from American Pie; he even looked like him. He was a Harvard graduate, his dad was an executive at a huge consulting firm, he was smart but incredibly ditsy and he tried really hard to be normal.
He walked into work one morning and asked one of his “trainees” if he/they got paid this week because he literally couldn’t see the difference in his bank account.
23. A Lexus for Lexi
A girl I went to high school with got a Mercedes for her 16th birthday. She got extremely mad about the fact that she didn’t get a Lexus.
Well, she wanted it because her name was Lexi and she thought it would be “Sooooo cool” for Lexi to drive a Lexus with a custom license plate saying “Lexi.” Her parents did cave in and buy her a Lexus for her 17th birthday.
22. She Has Never Been Poor
I worked for a non- profit that helped extremely low-income women start their own business. These women would give up food to scrape together enough money to join our program. One of our E.D.’s said, “she wished she could relate to our clients more, but she has never been poor.” She owned two homes in one of the most expensive zip codes in the US.
Also, another woman, whom I really did respect but not always agree with, believed people chose to be in poverty. We would debate for days about that statement. I realized working there that people who run advocacy programs for poverty have no idea what it’s really like. It motivated me to go back and get a Masters degree to fight this. I grew up super poor and can speak from experience, not theory.
21. “They Make Things Better Over There”
My cousin’s best friend yelled at her dad and said that she hated him because he wouldn’t take her to London to buy a dress.
Mind you, the same dress was available from the same store back home. But still, she didn’t like it and said she needed the one from London because “they make things better over there.”
20. Ignore The Call, I Can Pay You Double
I once had a mom ask if I could open up the back of our ambulance so her kid could see what was inside since he “wanted to be a firefighter” (I’m a medic, not a firefighter). I agree as long as he doesn’t touch anything. Of course, the second the doors open, the kid hops in and goes straight for our expensive monitor. I tell him no, that it’s dangerous and the mirror could break, to which he starts screaming “I don’t care, my mom will buy it.” The mom says, “it’s fine, just let him play with it; if it breaks I’ll replace it.” I had to physically pick him up and carry him out of the ambulance since she didn’t even try to control him.
While this is happening, we get paged out for a call and this lady suggests that she would pay double our hourly wage if we stay for a few more minutes so her child could explore/destroy more of our equipment! Someone could be dying! Just what was she thinking?
19. My Yacht Is Bigger Than Yours
My rich uncle owned a super yacht and loved to travel around the world. Apparently, his favorite thing to do was pull up into a port and bathe in the stares of everyone admiring his yacht since it was always the biggest one.
Well one day, he goes somewhere, say the Bahamas, and he pulls into the port and he isn’t getting the usual attention since someone else happened to have a bigger yacht than him for once. And guess what? It ruined his entire weekend. He was in a terrible mood and couldn’t enjoy anything.
18. Spoiled Brat Detected
A young girl, about five years of age, was getting ready to go into New York City to visit her grandmother. She was at her aunt’s house and did not have a pair of shoes that she liked.
She called her chauffeur, told him which pair of shoes she wanted and he went and got the shoes, driving some 20 miles to deliver them. When he arrived, she told him he got the wrong ones and called him an idiot. And no one in the family thought this was inappropriate.
17. It’s The Wrong Color
I had a scholarship to a private school for my secondary education (11-18.) We were by no means poor but compared to the people who were paying full school fees, I was a peasant. Most of the kids were given cars for their 17th birthday in anticipation of passing their driving tests. One boy, in particular, had a September birthday, so was one of the first to take his test; he had a huge house/garden, so he already knew how to drive (you can drive on private land at any age).
On the day he passed his test, he got dropped off back at his school in his shiny new sports car. He picked up a couple of friends to go for a spin, and before he got 100m up the road, he completely wrecked the car. His dad bought him a new one the next day and he complained that it was the wrong color.
16. Too Many Properties Are A “Hassle”
My boss complained to me recently that they owned too much land and too many properties. She said, “don’t own too much land and properties, it’s just a hassle.”
I just laughed awkwardly, thinking I would be happy to relieve some of your burdens by accepting some of that land and properties, ma’am.
15. Landscaping Vehicles That Cause “Health Problems”
I used to work for a landscaping company in one of the richest areas in the Toronto suburbs. Most of our customers behaved reasonably (most, not all) because they appreciated that we were doing work for them, but we got all kinds of complaints from neighbors about having to see work vehicles on their street. One guy told me that it was crap that he had to look at us and our truck because he paid so much in property taxes.
Another one claimed to own the section of road in front of his property and even called the cops on us (who thankfully laughed at him). When the cops didn’t do anything, they e-mailed my boss threatening legal action because the stress of seeing a work vehicle on the street once a week was giving his wife health problems.
14. The Supplementary Income
I know a garbage man that works in rich neighborhoods and takes out the trash for the uber-rich-kid university. Every year, he finds 200-300 game consoles (the newest ones) and sometimes desktop PCs.
Apparently, the kids don’t want to take them home, so they just throw them all out. He makes a good $40,000 a year on eBay. He just cleans stuff up and sells it; it’s a nice supplementary income.
13. 1 Mbps is A HUGE Difference
I live in the part of my country where internet is really expensive. For instance, 16 Mbps plans are considered plans for extremely rich people.
One fine day, one of my friends threw a fit at his dad because he was getting 15 Mbps instead of 16 for about an hour.
12. “You Can’t Put a Price On A Good Time”
A group of rich high school kids in Montana was out driving around and drinking. They found two combines (large farm tractor thingies, worth about $250k each) out in a wheat field and decided to have a demolition derby. They ended up getting caught.
In the judge’s chambers, with the farmer, who just wanted the damages reimbursed, the high-end family lawyers asked what the hell they were thinking when they did it. Their response? “Well, you can’t put a price on a good time.”
11. Friday Isn’t Part of The Weekend
My college roommate’s mom gave him $1400 “for the weekend” randomly. He blew through the whole thing by Saturday, spending it on buying girls and drinks (particularly bottle service)over the course of Friday and Saturday night.
He then asked his mom for more money and was screaming at her because “she promised $1400 for the weekend.” His argument was that she was being unfair because Friday isn’t a part of the weekend.
10. Firing People For the Heck of It
My mom has a new boss at her not-for-profit domestic abuse prevention job. The lady didn’t like the line of work and had even told some of her employees she was only there because she enjoyed not asking her husband for spending money (which is actually respectable).
However, she didn’t like her work environment and had over half of the current staff replaced with people she felt better suited her work environment. Within two months of her arrival, six of the women earning less than $40,000 a year (most of whom who were single and depended on the income) were let go, just so this woman could find her workday more tolerable and so she could spend her money on non-essential crap.
9. “I Know Why I Hired You”
I worked as a personal assistant for a U.S. Ambassador and his wife. I worked at their house doing odd jobs; basically whatever needed to be done. One time, the ambassador’s wife opened the door and said, “Oh, thank god you’re here.” She literally pulled me by the arm in the kitchen, then handed me an empty black garbage bag that looked like it had been mangled on the top. “Can you open this?” she asked dramatically. “My husband and I tried for half an hour last night.”
And as we all would have, I rubbed the top of the bag, grabbed the two sides with either hand and snapped the bag open by filling it with air. She looked at me, stunned. And then she said quite seriously and enthusiastically, “[My name], it’s times like this I know why I hired you!”
8. Stairway To The Bank Account
My neighbor is this really down to earth guy who managed to work his way from nothing to being super wealthy. A few years ago, he married this beautiful girl that can safely be said to be on the upper scale of maintenance cost. She was given perhaps too much freedom when they redecorated their mansion and ordered custom made stairs that cost about $100,000 and was made of glass and steel.
Once she had them installed though, she noticed that they didn’t really match her choice in furniture so she had a virtually identical set of stairs made that only differed from the last set by a few shades of white. How this guy put up with her is beyond me.
7. Mats Matter
I went on an amazing trip with my girlfriend at the time during the summer and she had an uncle who was very rich and she was used to all his wealth. I was not. On the third day of the trip, I was getting aboard his yacht (he owned the largest one in the club) and it was incredible with glass stairs, stone walls and beautiful dark wood. We all sat down near the back at a table and the wife freaked out. She yelled, “Where are the mats?!”
Apparently, there were supposed to be ‘mats’ set down on the table before the giant glass bowl of chips and freshly made guacamole could be placed in front of us. She was really mad and almost embarrassed. I’ve never been so weirded out by someone’s anger. I couldn’t believe that it was SUCH a big problem.
6. No Walking, Just Taxis
One girl would take a taxi everywhere in town. It was a very safe, small college town with free campus buses but she’d still taxi across campus. She lived two blocks away from me and would take a taxi from her dorm to my house; according to Google Maps, it’s a full 4-minute walk.
She swore she just had a terrible sense of direction and couldn’t figure out where we lived, but you’d think after the first embarrassingly short taxi ride she’d throw our address into a map and just walk.
5. Sixth Car’s the Charm
A kid in my high school crashed six cars within a year. And they weren’t like the 1990’s Toyotas and Hondas most high schoolers buy themselves; these were brand new Subaru STI’s, a BRZ, a BMW, brand new Jeep, and other vehicles like that.
The last car his dad bought him was a semi-new Ford Focus. It was a decent car and much better than my 1997 white Camry, but every day he complained and threw a fit because his dad wouldn’t buy him another $30k+ car.
4. The Gospel of Money
My mom works at a Baptist church where the pastor makes somewhere between $90,000-$100,000 a year and has all his insurance and gas paid. He is rich as heck, owns two homes and has a ton of money on top of his salary.
When he takes mission trips and pastor conventions, he holds offerings to pay for his airfare and everything else. Meanwhile, other people that come with him pay their own way. This is a church full of poor and retired people and the pastor is living like royalty.
3. All For The Horse
My dad is a self-made millionaire. He accomplished it through hard work, and he raised me just as toughly as he was (he didn’t want me to depend on money). But I have some experience with people of my “status” not being nearly as grateful as I am. One girl I know convinced her parents to move, so she could be closer to the horse stables she liked to ride at.
She upped her dad’s drive to work, and her mom’s, and her little brother had to change schools in the 8th grade, which is the worst time to pull a child out. She also made her mom BUY her favorite horse, which she then tried to sell to me. She said, “I was rich and I didn’t need my money like she did.”
2. How Rich People Torture Their Kids
My ex-wife used to drive a 1998 Honda Accord. She treated it like trash and so one day, I got into it to drive somewhere and noticed that it was falling apart. I had two options: to bring it to the junkyard or to sell it. I chose to put it on Craigslist for $250.
I thought it could go to a low-income family that had someone with some know-how who could semi-restore it, but when I meet the buyer, he was not who I expected. He pulled up in a brand new Escalade and told me that he that his son was spoiled. His son had crashed a BMW, Mercedes, and an Audi and so he was done buying him nice cars. It turns out, this guy purchased my car as a way of torturing his son.
1. Buying Used Stuff= No Dignity
There was this rich kid in our class who was literally disgusted by us buying used stuff (like computer parts) on eBay.
Once during a conversation, I said that I bought a memory module for my computer on eBay and he said to me that I should have a little dignity, and if I buy used stuff I should keep it to myself.