When the time comes, everyone needs a will. But some people decide to use their wills for purposes way beyond the pale. From extreme delegators of the smallest items and bitter jabs at un-favored relatives to jokesters trying to send a laugh from beyond the grave, these are, hands down, the weirdest wills we have ever read.
1. The Golden Rule
A good friend of mine looked after an older lady. She was his neighbor and, as far as he knew, she had no family. So, he was at her place every day when he wasn't working. I met her a few times, she was a sweet old lady. She had three cats that were her babies, she spoiled them to no end. She even had a "cat room" for them.
Well, one day after my friend had been looking after her for a few years, she passed peacefully in her sleep. He found out that she named him in her will. He attended the reading and found three 20-something ladies there too. Turns out the lady had moved across the country unannounced a few years earlier, and had disappeared from the daughters’ lives.
The old woman left my buddy 19. Million. Dollars. She left the cats to a lifelong friend from her home state and donated all of her belongings to the Salvation Army. And her daughters? Each received, "A single litter box and all of its contents," along with one $20 bill each to "give them each a last taste of all she was to them". That sweet old lady is my hero.
2. Everything is Better With Bacon
A co-worker of mine has it in his will that before he is cremated, he wants to be wrapped in bacon. He has no family and a lot of money and this dude really loves bacon. He said it's going to cost somewhere between $2,000 and $2,500 to be cremated in bacon, but it’s totally worth it to him.
3. Great Ride
I did a few pro bono wills. This big guy asked me to give everything back to the community because he had no living immediate family. No problem. Then he told me his one exception: his Vietnam-era motorcycle. He said it was the first thing he bought after getting home from service, and he wanted to be buried with it, literally on it and in a riding position. I helped him set aside the funds necessary to do it. Dude was awesome!
4. It’s All in the Cards
My law professor told me about a client who left his three sons and grandsons his extensive baseball card collection. It seemed normal when my professor first heard of it; but then, he was handed a handwritten chart that had several hundred cards listed in one column, with the name of the recipient and why that person was getting the card in two more columns. "I leave this pitcher to Bobby because Bobby can't throw".
5. Like a Carrot on a Stick
My mom only works for crazy rich people. The worst will she ever told me about was this old guy who was close to 90. He wanted it so that when he passed, all of his millions would go into a trust for his kids. The catch was that his kids would never actually be able to touch it; they would only be allowed to collect the interest it generated. But it gets even worse.
He had my mom set him up with a group of accountants who will manage the trust, and he specifically arranged a plan with them to manage the account in such a way that their yearly billing will almost exactly match the interest to be made. So, when he dies, his kids will inherit millions but will only be able to spend like 35 dollars a year from it—35 dollars that the kids have to split between them!
6. Talking to Titus
My dad is a bit of a jokester. He frequently tells my brother and I that his will has a stipulation that he be cremated and his ashes be baked into a loaf of bread. Then, he goes on to tell me and my brother that we have to eat said loaf of bread to qualify for any inheritance. That’s not even the scariest part. My dad is a lawyer—who writes wills!
7. Munificent Motivator
Client: "I'd like to leave $100,000 to my son, $100,000 to my daughter, and $10,000 to each of my ten nephews". Lawyer: "But sir, your estate is worth about $500. Where are your heirs supposed to get this money from?" Slamming his cane on floor, the client roared, "EARN IT, JUST LIKE I HAD TO!!"
8. Sweet Tooth
My grandpa originally had just two grandkids, my brother and I. He has a collection of nice cars. Originally, I was getting his two Corvettes and my brother was getting his Cadillac and a race car. Well, my aunt and uncle finally coughed up some kids, and my mom is about to have another baby, so now there are eight grandkids. He's announced that he will be having a contest for the cars. The contest is to make him an apple pie that tastes just like his mother's.
9. A Shocking Turn of Events
The strangest, and most embarrassing, will reading was in a room crowded with relatives when a man who passed fairly young left absolutely everything to his 26-year-old stepdaughter, which was quite a lot of money and property. The two ex-wives and his children from the first marriage got nothing, nor did siblings, nieces, nephews, etc. The will specified that a DVD be played to explain why the stepdaughter was getting everything. Like everyone else, I thought it'd be the guy explaining the big "screw you" to the rest of the family.
What followed was completely unexpected. It was a hidden camera recording of the guy and his stepdaughter going wild in bed together. The video started in mid-action, with her screaming "yes oh god yes!" It had obviously been edited to start with maximum shock value, and it worked, because it took about 30 seconds for me to recover enough to turn the thing off. It was definitely the biggest "holy moly" moment of my career.
I later learned that the guy and his stepdaughter had a relationship since she was a teen, all the way to when he passed (when she was 26). Apparently, though this is second-hand and I can't confirm, there were multiple clips of various video bits through the ages on the DVD. At the end of the DVD, the guy explains that the stepdaughter gets everything because she'd been "the best lay of his life".
The worst part was that the will specified that I was to give every single family member their own copy of the DVD. The copies had been kept in a box and had been distributed prior to the showing, so everyone had "The Best Moments Of" in their hands, at the time the DVD was playing.
Epilogue: the family sued and lost, believe it or not. The girl got to keep everything.
10. Breakfast at Tiffany's
My mom is an elder law attorney, and she has some pretty crazy stories. Once, she had to buy and distribute $166,000 in Tiffany's gift certificates to 43 recipients who were a mix of family, friends, and ex-girlfriends. Ten received $10,000 gift certificates and 33 got $2,000 gift cards. She bought them with credit cards and flew me to Europe with the points she earned.
11. A Sweet Surprise
When I was in college, a faculty member passed and left his money to the college. In the will, it said, "I don't care what you do with the money, throw the kids an ice cream party or something". And that is exactly what the money was used for; they threw a gigantic ice cream party.
12. Clowning Around
Knowing how status-conscious her greedy relatives were, one lady decided that she would make them suffer for it. When she finally passed, her lawyer approached the family with instructions for her final wishes. According to the will, the only way the relatives could get the money is if they followed the funeral instructions to the letter.
I don't remember all of the absurd details in her instructions, but the central theme is pretty unforgettable. She required an open-casket funeral, with all family members in attendance—and demanded that her body be dressed up like Bozo the Clown, including makeup, red nose, crazy hair, massive shoes, the works.
The family tried to protest, but the will was extremely clear. They either attended the Bozo the Clown funeral, or they didn't get a dime. So they did it. These stuck up vultures had to stand there for hours, glowering, taking weird looks from all of their friends & neighbors as people got close to the casket and realized the deceased was dressed like a clown!
According a funeral parlor employee, the best part of the service came when they tried to shut the casket... and couldn't, because the massive shoes got in the way. They had to bend these 24-inch shoes in half to get the lid closed.
13. Post-Mortem Helicopter Parenting
A woman had fallen out with her daughter because she hated the husband that the daughter had chosen. This feud went on for years, to the point where they never had any contact, because whenever they did, things would just get pretty ugly. The daughter refused to leave the husband, and the mother demanded that she did.
So, when the time came to read the will, the daughter was surprised to learn that her mother had left her a good portion of money. However, there was one stipulation: she got the money on the sole condition that the daughter change her surname and her children's surname back to her maiden name, effectively removing this hated husband's name from their family tree.
By the sounds of it, this was a real sticking point for the daughter and the solicitors were pretty confident that the daughter was going to forsake her inheritance, which was a pretty large one, in order to keep her husband's name.
14. Creature Comfort
I had this little old lady come in who was a referral from one of our clients. He said she was a little bit strange, but nothing too odd. She had four children, and her husband had passed. She also had a couple hundred thousand dollars in various bank accounts, plus a house. So, she appointed her friend as executor and trustee, with instructions to sell her house when she dies.
A sizeable portion of her estate was to go to some weird church. The rest of her estate was to be invested and used to house her three little dogs. Those dogs are going to be much more wealthy than me in a couple of years!
15. Isn’t it Ironic?
My father in law always said his favorite story was about an old lady who was worth around 15 million and had five kids. One of her daughters married a horrible man, who would spout the foulest, most prejudiced statements he could think of. When the old lady passed, each child got 3 million—except for the wife of the foul man.
Instead, the old lady donated that daughter's inheritance to things that her tool of a husband liked to complain about, such as historically Black colleges and universities, Planned Parenthood, the Special Olympics, her local synagogue, food banks, etc., because she felt that they ‘both deserved to be penniless and hating each other for being awful human beings.'
16. You’ve Got it, Sparky!
I once wrote a will for a Lance Corporal, who was told to get a will before deployment. He was a young, single fool. Two specific provisions concerning his funeral stood out: he wanted to be dressed in an Armani suit, and he "wanted to be burned". Naturally, I inquired as to the latter. I said, "Like a pyre?" He didn't know what a pyre was. After a pause, he said "I just had it in my mind... that I'd like, be on the ground... just, burning".
17. Father of Nostalgia
A client had two sons. He left a whole bunch of specific distributions to one of the sons; his truck, firearm collection, etc. To the other son, he specifically left one thing: a poster of himself in high school. I have no idea if there was some significance or sentimental value behind the poster or if it was more of a "look at what I'm giving your brother—and here's a poster of me so you will never forget that I loved you less" situation.
18. A Little Fishy
A lady wanted to create a trust fund of £100,000 for her pet fish. When I asked if it was a special kind of fish, she confirmed that it was just a normal goldfish, but that she wanted it to be fed fresh avocado every day and be looked after by a local dog walker after she passed. She was absolutely serious.
19. Dress to Impress
My grandfather left me a navy blue tie with pink elephants. It looked ridiculous, but my grandmother said that he wore it to intimidate people in business. He thought that someone willing to wear such a ridiculous tie projected the idea that he didn’t care about what people thought, and that scares people. He wanted me to have it so I could do the same.
20. Making a Point
My great uncle's official will gave the contents of his outhouse to the City Council of a nearby town after they tried to take his land twice to build a new water treatment plant. He spent quite a few years fighting imminent domain claims and just wanted to give them something in return. As a joke, his kids boxed up all the books and magazines in the outhouse and dropped them off at City Hall.
21. Aquatic Authorization
The city I work for was renovating a small park that was donated to the city in the 1910s. We went looking through the hand-written deed for easements or other restrictions and found that the family could reclaim the property if the park was not, "perpetually provided with a fountain of pleasant running water fit for consumption by man and beast alike". The family still had descendants in town, so we installed a new water fountain with a dog bowl filler, just to be safe.
22. Litigious Librarian
My dad’s partner had a lady come in with an itemized list of books. She wanted her will to contain a record of all of the books and their recipients, based on her choosing. The truly astonishing thing is how many books she had, and how specific the assignments got. Her list is currently at about 2,000 books and is to be divided among about 30 people. She apparently comes back at least once a year to add all the new books she’s gotten.
23. Forgotten Lunches
My favorite was this man who left some of his kids just a dollar because it was easier than leaving them out entirely, but then went on a massive rant about how he tried to go to lunch with them and sometimes they were too busy working, and it was unforgivably rude, and they should use this will as a wake-up call to treat their elders better. It rambled just like that, and I remember it being very specific regarding dates and times of lunch requests. That portion read like a diary. I bet they were sorry.
24. Taxi Driver
One of our clients passed recently. Turns out the man she left almost everything to, including the residue of her estate—which was considerable—was her regular taxi driver. She had also named him as her executor. He had no clue. The person who had been named as her executor and main beneficiary on her previous two wills, a close friend of many years, was understandably flabbergasted and contested the will. We informed Mr. Taxi Driver, who didn't even know our client had passed, and the will was upheld.
25. Tell us What you Really Think!
My grandfather left my uncle three things from his rather valuable estate: one dollar in unrolled pennies; a framed copy of the contract my uncle signed saying he owed my grandfather $100 000, which he had never repaid; a framed copy of the letter my uncle sent my grandfather saying he was disowning my grandfather for "being cheap". I was only a kid, but I understood.
26. Purr-fect Lifestyle
One client left $100,000 to his two cats so that they could "maintain their current lifestyle".
27. No Excuses
My sister used to work for a non-profit that frequently received bequests from wealthy estates. The non-profit has been around for at least 200 years, and they have some really strange old bequests still kicking around. One is particularly memorable. Apparently, they get money each year on the condition that they arrange to ship a set of books to Liberia every summer.
28. Grandpa Charlie?
In his will, my grandpa instructed that a chocolate bar should be given to each one of his grandkids. Unfortunately, I have 12 cousins, and some were very difficult to track down. All other items in the will were frozen for months because they couldn’t find everyone, and we eventually had to go to court. The lawyer that was helping execute the will was blown away that the stipulation had been allowed. I’m not complaining, though; I got a Toblerone out of the deal!
29. Booby Trap
I was forced to write a will due to the health insurance I get at work and, amongst the sensible stuff, the in-house lawyer said it was totally okay for me to add this clause: "My funeral wishes are that I be buried in a coffin which has been spring-loaded, such that opening the coffin would cause alarm to future archaeologists".
30. Spit Happens
My great aunt had about $2 million when she passed; she left half to a small church in the middle of nowhere and the other half to a llama sanctuary. She left each of her family members about $25. She had no children of her own, and most of the extended family was greedily making plans for how they'd spend her money. It was her final revenge against them. I was about 9 at the time, and was thrilled at the $25 I got.
31. Better than Weight Watchers
One client set it up so that his will could be awarded in financial installments to his daughter. The only catch? His daughter had to remain under a certain weight. I was flabbergasted. It didn’t even make sense, because she was not and had never been overweight! Dude was controlling her diet from beyond the grave.
32. Read Between the Lines
My grandmother specified which of the children and grandchildren should get which of the family recipes, and somehow felt the need to include commentary about why certain decisions were made. One was a Prohibition-era recipe for beer that I knew my uncle, also a homebrewer, wanted, but she left it to me, with the comment, "I know you wanted it, Teddy, but my granddaughter has the second-best penmanship of the girls, and will make you a copy".
And then, like eight pages later, in among the specific descriptions of her vast collection of romance novels was this line: "And this book to my granddaughter, who will please subtract about half the hops before she copies the recipe for her Uncle Teddy so that any of us can drink it. Our Jon had his IPA last summer and just about collapsed".
Uncle Jon just about burst into tears laughing and Uncle Teddy had long since left the room because he didn’t care about romance novels. I have no idea how she got this will done. My guess is she wrote it herself and the law students who came to her independent-living building signed off on it. There wasn’t much value in the estate, so it was mostly a funny last letter from Grandma.
33. Surfacing Secrets
A client of mine confessed to me that she has a secret daughter. She wanted to leave the daughter some money and photographs without the rest of her family finding out, because nobody knows about her. Even her husband does not know. That will be a fun conversation when she passes away and the will is read!
34. A Family Tradition
My great grandfather had a pair of socks that he only wore on Christmas Day, for Christmas dinner with the family. They were hideous. After he passed, we found out he had left those socks to my uncle in his will and instructed him to carry on the tradition, which my uncle has done. I've already been told I'm getting them next.
35. Lifelong Catch
One interesting case in inheritance law that I came across was the one of a rich owner of a private bank, who left his shares to his sons under the condition that they act as managers of the private bank, but with a personal liability concerning the bank's debt. What he did essentially was give them the money and commit them to lifelong work in the bank, while putting their own assets at risk.
So, when one of the sons decided to sell his shares because he was old and sick, the courts had to decide whether he would receive any money at all from the will, as the condition was technically not fulfilled anymore, as he had given up the manager position.
36. Favoritism at its Worst
A will from 1986 included the craziest provision I have ever seen. It stipulated which of the woman’s three sons would be allowed to name one of their children after her. Apparently her name had been "in the family for time eternal," and she wanted to make sure the best son was the one who carried it on. It also included a summary of why only one of them, the youngest son, was worthy of the right. It was pretty cruel to the other two.
37. Mothman’s Aunt
My great aunt, with whom I barely had any relationship, left me a taxidermy giant silk moth that she had hanging on her wall. Evidently, someone had told her about my love for bugs. I still have it and it's one of the coolest things in my collection of odd knickknacks. She left my cousin a Furby.
38. No Fighting This Will!
Sometime in 1995 or early 1996, an elderly woman left over $2 million to the professional wrestler Shawn Michaels, who she had never met, just because she enjoyed watching him on TV. It’s not like he needed the money either; he'd have been making over $500,000 a year at that point.
Wikimedia Commons, Felipe Bascuñan
39. Shout Out
My grandfather has a rather unique will. It directs the lawyer to say, "hi so-n-so," to several people, just so he can say that he mentioned that person in his will. He tells lots of people in the family that they are "in his will". It’s a joke that only he thinks is funny, and he won’t be around for the punchline. I think it’s brilliant. He has about 10 people mentioned.
40. The Last Laugh
My Dad had a quirky sense of humor. In his will, the note under my name was as follows: "throw this rock at my son and hit him in the head with it, but make it surprising". I was thinking, what kind of a will is this? Then I read a little further on...and found that he had left a note saying, "this is the rock that my son hit me in the head with when I was teaching him how to skip rocks".
I had apparently hit him so hard that I dented his skull above his ear, and it never really healed. It was the most meaningful thing he’d ever done, and after all the years me and my dad had messed around with each other, it was his way of winning and taking the final crack at me. It was so heartfelt, it moved me to tears. He got the last laugh and I was completely ok with it.
41. To Beyond the Grave
I advised on a will where the deceased had left considerable assets to people who had already kicked the bucket by the time the will was read. There is nothing unusual in that per se, except that these individuals were long gone when the will was made. The lawyer apparently asked the guy, "You know you're giving your money to dead people?" and even sent him to a doctor to make sure his mental state was okay. The doctor gave him a full bill of health and said he was perfectly compos mentis, so the will stood.
42. Meticulous Planning
I had a client who insisted I write this in her will: "To my daughter Anne, who created my beautiful granddaughter Jane, and her dear fourth husband John, who laid hands on my Jane, I leave one dollar, you money-grubbing hooligans. To Jane, I leave all of my monetary assets, save $5,000, and my best firearm, which I leave to my son Bill, on the condition that he confronts John with it during the time between my funeral and my burial. Jane, bail your uncle out of jail, please".
43. Reverse Golden Rule?
My father has been heavily involved in my great aunt and uncle's lives since their health began to decline. They are both in their mid 90's with no children, and my father has seen their will. They have a small fortune in excess of $1,000,000—and have left it all to a local dog's home. When my dad asked them about it, my great uncle's response was "nobody has helped me in life, so I won't be helping anybody either".
44. Nit-Picking
We had an 84-year-old client who was, in the simplest terms, quite insane. She would call every single month to change her will. It would always be small details, such as removing her daughters because they hadn’t called her in a while, or increasing one child’s percentage and lowering another’s based on whether she was mad at them or not.
But there was one part that she would never change: what she would leave for her dog. She wanted to leave her dog $25,000, plus more money for the care of the dog and to make sure she lived comfortably. Sadly, her dog passed on before her and she had to remove that part from her will. So, she just went back to playing with the percentages that her daughters would receive.
45. Centre of the Family
My great aunt, who had no children, put in her will that a certain percent of her money was to be distributed evenly amongst her nieces and nephews. She stipulated that the remaining money would go to my dad, as long as he used it to throw a big family reunion party. Even after she was gone, she brought the family together; it was a great party in her honor!
46. Better Get on Tinder
My folks have informed me that I will only be inheriting debts if I do not produce a legitimate child. In that case, all assets will go to my sister. If I do have a legitimate child, which they're defining as "must pass a paternity test" and I have to be married to the mother, then the split of assets and debt is 50/50.
47. Surprise!
A regular customer at the store I worked in told me he was terminally ill, which upset me because I'd gotten to know him well. He was a good guy, and it turned out that he had quite a bit of money. He had a daughter with whom he was not on good terms. He told me that he was leaving her "the contents of his bank safety deposit box". It sounded nice, but there was a huge catch. Inside, he left a bunch of pop-up snakes, primed and ready to burst out when the box was opened. Then the rest of his estate was to be used to fund the building of a respite home.
48. Scrupulous Script
My grandpa left me all his tools, a pretty good chunk of change, and his dog Tanner. But, to get it I had to do some...strange things. According to the fine print in his will, I have to make sure his live-in girlfriend at the time got nothing at all, and tell my uncle that he was fat and his wife was going to leave him if he got any fatter. There was literally a script inside the will.
49. Spoiler Alert Will
Two sons of a really wealthy couple go to the family lawyer to have their recently deceased parents' will read. The lawyer is super nervous because he has known them both since they were kids. One son gets the entire inheritance, and the other gets nothing. The explanation was that it should be passed through to blood relatives only. So that was the day he found out he was adopted.
50. Benevolent Beggar
I had a guy be extremely charitable when we were drafting his will. He left a million to his church, two million to a local hospital, and another two million to the American Heart Association. Then we gave him a quote on how much it cost to draft the will, and it wasn't much, because it was a rather straight-forward document.
He asked for a payment plan; he couldn't afford the will. The dude had no money! He thought you could just leave money to people or organizations, and that the government would foot the bill. He got really mad when we told him that wasn't how it worked.
Sources: Reddit,
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