October 15, 2023 | Miles Brucker

These Crazy Wills Prove That Drama Never Dies

Drawing up a will is hard. A person basically has to boil their life down to a few pages of paper. Many people use their will to divvy up their possessions, but others walk a different path. These people used their wills to say their piece, get their final punches in, cause some chaos, and crack that one final joke. You may want to check in on your loved ones after reading these wild stories!

1. Spoiler Alert Will

Two sons of a really wealthy couple go to the family lawyer to have their recently deceased parents' will read—and that’s when the family’s deepest, darkest secret is revealed. 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.


2. Help Thy Neighbor

My dad knows a guy that used to work with drywall. His neighbor was this old guy that lived alone. He'd go over and mow the guy's lawn and help him out around the house in his free time. When the old man passed, he left everything to the guy, including, get this, a million dollars. My dad's friend took the money and started his own auto body shop. He still works there today, even though he doesn't have to, and he's the nicest guy in the world. When he fixed my car, he refused to take any money for it.

Crazy Wills FactsShutterstock

3. Wrestlemania

One time, I had a young client come in to create a will before his deployment. His will was quite special; he requested to be buried in blue jeans, a Chris Jericho T-shirt, and his replica WWE championship belt. Luckily, he did not meet any misfortune on his deployment and still has time to change his will for the future.

Crazy Wills FactsWikipedia, Gabriel Araujo Schott

4. King of Coffins

My cousin is a career Marine and once told me that in his will, he put that he wanted a Budweiser coffin. I thought he was joking. He was not.

Hurtful Comments factsShutterstock

5. Fly-in Uncle

I had a rich uncle. He was real crazy…and not in a good way. He would come to visit us when we were kids, maybe once every ten years. The last time that he visited, he brought us to a Denny's. When he arrived, he met my brother at an airport, was with us for an hour, and then he got on another plane and went home. When he passed, he had no friends, and he had basically driven his wife to drink herself to the grave a few years prior. In his will, he left his entire estate to an Elvis impersonator. Everything.

Crazy Wills FactsShutterstock

6. Keeping the Good Times Alive

My dad’s friend passed, but before it happened, he opened up a bar tab with $5,000 prepaid at the horse track where he and my dad originally met. The tab was not just for my father, but for him and ten of their buddies who hung out at the track together. I thought that was pretty cool. To this day they still put drinks on his tab.

Human Attraction factsPixabay

7. Coerced Confessional

My grandmother was adopted and an only child. She took care of her parents until they were gone. A week before my great-grandfather passed, the pastor from their church locked himself in the bedroom with him and had his will changed. When the will was read, it stated that my grandmother was not a person of any relation to him and nothing from the estate was to go to her.

Also, the pastor had her adoption records destroyed so that there would be no proof of a relationship. Because of this she could never find out anything about her birth family. Instead, all of his estate went to the church. My grandmother was understably a little raw about this.

James Dean DactsShutterstock

8.  Waiting for the Bus

When I was younger, I worked at an attorney's office. We had a client who was a little old lady and when she passed, she gave her house and all of her belongings to a bus driver. The bus driver was nice to her and would help her out, so she felt like he deserved more than her family. We were all waiting for a riot to break out when her family found out.

Crazy Wills FactsShutterstock

9. Joke's on You

I sat my wife down to have "the talk" because I was getting ready to deploy to Iraq. This was during the incredible sectarian dispute, and I wanted to make sure she knew everything to do in case something happened to me. She's never serious. Ever. But I wanted her to be serious for this discussion because it was important.

I get through telling her all about it and want to know if she has questions. "Yeah, so... the life insurance. How does that work?", she says. "I don't really know, baby. What do you mean?" She answers, "Well, do they just put the money in there? When?" I'm sitting there thinking, "That's weird but I know she's not trying to be cruel. She just wants to know the logistics."

That's when she says, "So do they put it in my bank account? Or do they give you one of those big checks when you win the lottery?" as she holds her hands up like she's holding a huge check. Laughter ensues. So now I have it written into the will that if I'm KIA, I want the $400K to be given to her with a gigantic lottery check.

Flirting or Being Friendly FactsShutterstock

10. Nine Lives of Luxury

My dad worked as a lawyer and he has a story that one time he had a woman leave millions of dollars to three stray cats that she had been feeding. After she passed, he had to go out and find them, catch them, put them in crates and ship them to a cat resort in Texas. It is safe to say that these cats now live a life of luxury.

Crazy Wills FactsShutterstock

11. My, That’s a Big Box You Got There

One client of mine was a guy that had a massive safety deposit box, like it was the size of a small dresser. There was a lot of tension before opening it. What could be in a safety deposit box so big? Surely something memorable! When we finally opened it, we found that it was filled entirely with coins. Several hundred thousand dollars’ worth of coins.

Crazy Wills FactsShutterstock

12. Monkey Business

My wife and I went to a lawyer to have our wills drafted. The lawyer told us about a client he had that had a great deal of money. His kids were fighting over it before he passed. Frustrated, the man decided that since he liked the monkey exhibit and the local zoo, he was just going to will all of his money and his huge estate to the zoo for the monkey exhibits. He now has a bench dedicated to his honor at one of the local zoos.

Meanwhile, his kids were ticked and tried to fight to get the money. They failed. The lesson is don't be petty or greedy, and love your family unconditionally.

Crazy Wills FactsShutterstock

13. One Hand to Rule Them All

Growing up, my brother and I played rock, paper, scissors over every little thing. No matter the issue at hand, we would throw down our hands and play for it. My dad had a nostalgic sense of humor and he decided to put it in his will that if both he and mom passed on together, my brother and I would have to play one hand of rock, paper, scissors for everything.

Weird Couple Secrets FactsPexels

14. Oh, Momma

In my office, we worked on a will that was quite demanding. The lady put in that one of her adult sons couldn't receive his share until he checked up on his teeth and visited a dentist. If that wasn’t enough, she also stipulated that the other son must lose 70lbs. before he took his share of the inheritance.

Fight Club factsPixabay

15. Spending Eternity Together

A lady I worked for put in her will that she wanted her cats to be cremated with her when she passed. I told her that’s not going to happen, human remains and animal remains do not get cremated at once. Being the nifty cat lady that she was, she came up with a solution: she settled on being cremated separately and then joined and buried together.

Crazy Wills FactsShutterstock

16. She’s Just Being Thorough

Typically, wills are about 10 pages (for the average person). But sometimes, people push their wills to the extreme. We had a lady who had a 56-page will. She detailed EVERYTHING, from her house to the people: “wooden ladle to ____”; “toilet paper holder to ________”; “magazine basket to _________”. This woman itemized every single item in her house, no matter how useless.

Crazy Wills FactsShutterstock

17. Zoo Day!

We had a man put in his will that his family was to go to the zoo immediately after his burial —the very same day! We thought that was the most heart-warming thing a client had in their will.

Crazy Wills FactsWikimedia Commons, Artur Andrzej

18. Secret Burial

One lady told us to put it in her will that she wanted to be buried next to her husband...on her property! She lived on a small rural property. It is totally against the law to have human remains buried there. Plus her husband had passed five or six years prior. So, it’s not as though it was 50 years ago, when things like that may have been a little overlooked.

Crazy Wills FactsShutterstock

19. Never Forget Your Disinheritance

Years ago, I worked in a retirement community. There was an older man who came out late in life and moved into the community with his gay lover. He was a Korea veteran with multiple honors and a wall of medals. He was also a bit of a jerk most days, but he had his moments and his stories were fantastic.

His children over three years never once visited him. He had a heart attack and knew he was on his way out. His children showed up but demanded his lover leave during their visits. In his will, he left everything to his lover and his lover's one child from a former marriage. He wrote a long note about his kids’ hypocrisy of not visiting and their attitudes toward his lover. But that wasn't all. 

He left each of his two kids a pail of coal ash, to be deducted from his estate. He also had his estate pay for his lovers' plot to be placed next to him and his wife, and in his long letter said that his kids, if they visited his grave, would be reminded of why they didn't visit while he was alive. Frankly, it was awesome hearing his kids explode with excitement about it.

Margaret Tudor FactsShutterstock

20. Bad Education

There was a rich old aunt who was the only one in her huge family with any money, having been a doctor on the Upper East Side of Manhattan. She set up a living trust to take care of her poor relatives in the Philippines, to continue as a testamentary trust whenever she passed. Her favorite niece was in control of the trust, and of course, the niece was responsible and even-handed and never embezzled any of the money to set herself up as a newspaper publisher and concert producer and media mogul with new expensive cars and lots of first-class pan-Pacific travel, nope, not her.

Who am I kidding, of course, the trustee did all that! Hundreds of thousands of dollars were missing, and an unholy mess of sifting through money transfers and property purchases in three countries. The niece also had a bigamous marriage to some guy in the Philippines (her real husband in north America was bedridden and slowly dying), to whom she sent buckets of her aunt's money to build a luxury villa. She vehemently denied such a relationship existed. She also had photos of the "wedding" on her Facebook page. She was not the smartest embezzler.

Crazy Wills FactsShutterstock

21. Harmful Parenting from Beyond the Grave

The weirdest will that I saw was a guy who wanted to set up a trust that stated his daughter could only receive a monthly payment if she remained below a certain (quite low!) weight. He was setting it up while he was still alive but it was a perpetual trust so that rule would stay in place after he passed. I can't imagine having such a controlling parent that they feel the need to dictate how much I weigh from beyond the grave!

Greta Garbo factsGetty Images

22. Next Level Tree Hugger

Where I went to college, there's an oak tree that a man deeded to itself in his will. Now called The Tree That Owns Itself, it sits in the middle of a road, and you have to go into another lane to drive around it. The story is that a man loved the tree so much as a kid that when he passed in the 1830s, he gave the tree possession of itself. This technically wouldn't stand up in a court of law, but the county and the local populace has accepted it and cares for it.

Crazy Wills FactsWikipedia

23. A Little Empathy Goes a Long Way

When my dad was growing up, there was this little old lady across the street without any family. She was from Finland and lost her husband during WWII. She immigrated to the USA and had no one. So my grandparents would knock on her door to chat, take her grocery shopping, etc. They also made my dad and brother help out around her house and yard. She loved my dad and uncle, treated them like her own kids and she gave them cookies and treats and presents.

When my dad was in Vietnam, she would record him voice messages on tapes and send them to him with letters telling him what life was like in the neighborhood and how she hoped he’d be home safe soon, that she prayed for him, etc. When he came home, he’d stop by to chat and help out around the house, bring her macaroons, and just sit and talk for a while.

One day she passed on, and a lawyer called my grandparents. She had left them a sizable amount of cash and stock, and her (paid off) house to my dad and his brother. My family had thought she was penniless. Never underestimate how much little, simple things can mean to people. You just might be one of the best things in their life.

Crazy Wills FactsShutterstock

24. Coming to a Family Agreement

This large French farmer’s family had been fighting each other for 15 years over their parent's estate. Everything and anything had been utilized in this all-out conflict; debts, spoils, barns, plots, cows, wills, and whatever. Defeats followed victories, failures followed compromises, and the conflict was tearing the family apart. Eventually, someone suggested they just drag all the stuff into the farm's courtyard, pour petrol on it, and set it all afire. Everyone agreed.

French farms with cows in front on green field pasturage on a summer sunny day

25. Hate is Stronger than a Will

My grandma’s sister was an extremely vindictive narcissist. She and her husband gained a significant number of assets over the years, including a somewhat profitable farm with over 100 acres of fields. They had a few children, all boys, and they all had wives and children of their own. Her husband passed about six years before she did.

Somehow, in their over 50 years of marriage and living on said farm, they had never bothered to go to a lawyer and write a will. Instead, she wrote a note saying that nothing was to go to her children, the wife of her son who passed almost 20 years before, or the grandchildren. She just left all her money in her safe. So, everything went into probate and the kids are still trying to figure it out. No one will say why their mom was so mad at them.

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26. The Jerk

My great-grandmother and great-grandfather had a will that would give their six kids a fair share when they both passed. But my great-grandfather passed, the oldest kid went to court to get his part of the inheritance, despite the fact that clearly, he was only supposed to get it after both his parents passed. This made my great-grandmother go off the deep end.

She didn’t get to handle the sorrow of losing her husband whom she been married to for 68 years. Instead, she had to go to court many times, and then she lost the house they had built and almost everything she owned. We helped her get an apartment and tried to keep her happy, but she deteriorated quickly after those months. I hate how someone can let greed come between families. I’ve never met the jerk.

Worst Thing Found in Hotel FactsShutterstock

27. Knives Out

Granny was a sweet old lady, relatively healthy but had some trouble getting around and taking care of herself. Her family was the typical greedy and money-hungry scenario, only calling when they wanted something. They stuck her in a nursing home and moved far away. To everyone's knowledge, Granny had very little money, but she still owned her property; a small house her best friend (my great aunt) took care of, and her car—a customized classic VW Bug.

The nursing home had volunteers, people to come and talk to the residents, play board games with them, basically keep them occupied. Granny's favorite was a newer volunteer, a 19-year-old girl whom I'll refer to as V. I only met her a handful of times, but V was a very soft-spoken and kind girl. V was the only volunteer Granny liked, because they had many things in common, one of those things being their mutual love for a specific kind of car...hint hint.

Over the next year and a half, V continued to volunteer about twice a week. Soon, Granny started to get sick, her health started to rapidly decline. Did her family come to see her? Nope. Until her last days, she only had V and my great aunt. Granny passed. Some of her family came to the funeral, but pretty much everyone only cared about the will. My great aunt said that the only ones who seemed sad at the funeral were herself, V, and a few of Granny's old friends.

When it came time to read the will, there was a big shock. It turned out Granny had a decent amount of money stashed away—about $100,000. The family was in the dark, only my great aunt knew about it. A very small amount of that was split up and given to select family members. But the rest was divided and given to my great aunt and V. V was in complete shock. The family was mad. A few other things were given to family, select items that didn't hold a whole lot of value. But it was about to get worse.

The car I mentioned earlier, the classic VW Bug? Granny's teenage granddaughter had her eyes on that car since Granny was put in the nursing home! Everyone expected her to get it once Granny passed. That didn't happen. Granny left it to V. If the family was mad about the money, they were FURIOUS about this car. Poor V cried her eyes out and said she had to leave the room. She told my great aunt, "I can't accept it. I'm not family, that car should be yours." And my great aunt spent over an hour and a half convincing her that Granny wanted her to have it.

Some family members followed V outside and started screaming at her, threatening to sue her, claiming it was part of a "plan" that V must have created (What? Befriend a lonely old woman and take her fortune?), telling her she didn't deserve any of what she got, and calling her awful things. One of the calmer relatives got things settled down and my great aunt got V out of there.

It's been a few years. My great aunt and V still talk, and V still has Granny's bug. As far as I know, after the reading of the will was over V got a lot of nasty messages online but was otherwise fine. One of the family members did contact a lawyer but they must have told them there was nothing that could be done since V never actually got sued or anything.

Crazy Wills FactsShutterstock

28. No Horsing Around

I have a client that doesn’t communicate very well with me, though he is quite special. In my town, there was a woman who left about a million USD to her horse. Yep! My client is a horse. We work managing his investments and the sister of the deceased pulls out about 3-4% annually to care for the beneficiary of the trust.

Shouldn’t Have Done That FactsPixabay

29. Grave Games

Creating a will can be morbid. But passing on is even harder, especially for the loved ones. So, I decided to try and make the situation easier for everyone after I am gone. My will stipulates that all my assets are to go to the niece or nephew that wins a treasure hunt that will be set up! It makes me happy to think about and I thought that would be more fun for everyone involved.

Crazy Wills FactsWallpaper Flare

30. Hunting for Candy

The client was a son who did not really talk to his father but wanted to make sure the father’s estate was wrapped up properly. They did not know if a will existed but knew that his dad had a safety deposit box. So, we get a court order to open the box, and sure enough, a will was there. However, the will left a lion’s share of his estate (maybe a few thousand dollars) to a woman no one knew.

Included in the will were also pictures of a woman without clothing and a stage name; possibly "cinnamon" or "candy," inscribed on the back. Soon it became obvious that the father had left part of his estate to a dancer whom he enjoyed visiting in his older age. She had no idea and they had to track her down, which was a nightmare. They finally found her and she came to the office for a check accompanied by a “male friend.”

Burial Customs FactsShutterstock

31. Paying for a Fake Daughter

For the last 10 years, my grandmother's brother had been paying child support and sending money to this lady whom he said was his girlfriend and the child "they had together." For years his other children and my grandma had been trying to convince him that the girl was obviously not his. He wouldn’t budge.

The "girlfriend" would appear only on payday and stay the bare minimum. The young girl called another guy dad and even had his last name. The "girlfriend" insisted he was just her friend, but the other children found out he lived with her and all. It was obvious to everyone, except to my great-uncle who we believe was just happy for a nice-looking lady to visit him.

He paid for their whole lives, house/school/vacations. The day that he passed, she was the first one at the door. He left her and her kid $1 each, with a note saying he had given them their inheritance while he was still alive.

Strange factsPexels

32. Finally Getting Payback

"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 jerks. To Jane, I bequeath all of my financial resources, excluding $5,000, and my prime firearm, which I entrust to my son Bill, provided he wins in a rigorous physical confrontation against John within the period from my funeral to my interment. Jane, kindly assist your uncle in securing his release, please.

Other than names, this is the exact wording of a great uncle's will. At age nine Jane told her mother that John had inappropriately touched her and her mother told her she deserved it for being a tramp. So, the great uncle took Jane in and raised her, and his two kids got exactly what it says.

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33. Let it Burn

A friend of mine is a lawyer. He had one client who, in accordance with his will, which also contained the permits to do so, had his entire estate burned while his family watched. It sounds cold, but apparently, the guy suffered and ultimately passed on from a fairly easily treatable cancer because he ran out of money and his relatives would not help.

white and red wooden house with white fence surrounded by treesScott Webb, Pexels

34. Dedicated to Mr. Bobo

When I was younger, I was working as a secretary and had to leave someone’s cats to various people, which is fine, whatever. But that wasn’t all. The woman had quite a bit of money tucked away, so I also had to donate money in the cats' names to various organizations. One of them was named Mr. Bobo. I enjoyed it thoroughly.

Unbelievable But True Stories FactsShutterstock

35. It All Happened So Quick

My maternal grandfather was wealthy. He divorced my maternal grandmother, remarried, and promptly suffered a heart attack. He was only 48 and had no will so everything went to his new wife, my mom’s stepmother. She was actually really nice and was planning on making sure that everything was "fair"...till she tragically passed in a car accident six months later.

She was a widow herself prior to marrying grandfather and had a now-orphaned a 15-year-old son from a previous marriage. He got everything. My mom and her siblings had to go to the auction at their childhood home and buy back as much of their heirlooms and memories as they could afford—and, truthfully, filched some of what they couldn’t.

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36. Back to Square One

My crazy mom left her house to her eldest grandson, my nephew. She also left small portions of cash to her other grandkids, the amount depending on her affection for them; a substantial sum to my erratic alcoholic brother; and a few thousand to me, with the condition that if I contested my share, I would receive nothing.

My mom pretty much had it in for everyone. I had my own attorney evaluate the will and he said it was legally hilarious and definitely vulnerable to challenge, but it would take a lot of time and money. I ultimately said screw it and I walked away with my few thousand bucks and got on with my life. The nephew who got the house renounced the will, as he was still in college. Applying for grants and scholarships, and owning a $500k piece of property would have wrecked his fiscal profile; he also hated the house and everything about it.

My erratic alcoholic brother moved into the place, spent all mom's money, ran up an astonishing amount of new debt using the house as collateral, and drank himself to the grave in two years flat. His equally erratic wife passed less than a year after that. Now I am executing her estate, which includes the house, on behalf of the grandchildren whom all got screwed in various ways a few years ago; the widow's will left everything to her husband unless he passed first, which he did, and named the grandkids as a fallback.

The bonus is, as I wrap this up, I have to work with the lawyer who wrote mom's evil, divisive will in the first place and facilitated the bit about how if I contested it, I got nothing. I suspect certain parties to this drama are going to the bad place, or they are there already.

Jackie Kennedy FactsShutterstock

37. On the Clock

This is the best will story I personally know. A father had a valuable antique grandfather clock, but also had two daughters so he didn't know which to bequeath it to. His solution was that if he passed on an even day, daughter A got the clock, an odd day and daughter B got it. The daughter who did not get the clock got an equivalent cash award based on the value of the clock.

Crazy Wills FactsShutterstock

38. For my Buttercup

An ancestor of mine in the rural UK in the 1700s left his farm and everything to his nephew (no children), with his surviving wife, only getting "the second-best bed" and a provision for her to receive 3lbs. of butter per week for the rest of her life. We thought this was incredibly mean, but we wonder whether this butter was meant as an income, I mean who can eat 3lbs. of butter?!

Strange Family Traditions FactsFlickr

39. Tears of Joy

A woman came in after her mother's funeral with some correspondence from the insurance company I work for. She was worried there was a bill she needed to pay and was coming to tell us that her mom had passed. She just looked SO tired, and we got to talking while I looked up the policy to close it out. She shared that in the last few years her mom had slipped into dementia and she singlehandedly took care of her. She missed her terribly, and was just run ragged.

That's when I realized that what she had was not a health policy, it was a life insurance policy naming the daughter as the beneficiary for about $50K. I told her and she just started crying. It made me cry and I got up and hugged her and sort of just held her while she cried. She pulled away and said..."I have no idea what she left that for, everything's been paid for." I said, "This might be her telling you to go on that vacation and relax." It was so touching, and she had no idea that the policy existed.

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40. How Do You Like Them Manure

I once amended a will for a doctor in which he disinherited his son by removing everything he had intended to bequeath and replaced it with a "manure spreader." I didn't ask any questions because changing a will is an easy thing to do. But one day, that doctor will leave this earth, and his son will have essentially be told to "eat it."

Crazy Wills FactsShutterstock

41. Farming is Not Just a Man’s Business

We had a client who was a widowed farmer that owned several heavy equipment machines (Caterpillar trucks, etc). He had two sons who were already working with him at the farm and a daughter who was working in the city. He willed the heavy equipment to the daughter. We asked him why he willed the equipment to his daughter, who lived in the city since the equipment was essential to the farm. He replied that the farm was to be split by his kids equally but he wanted to dispel his daughter's alienation from the farm over being a girl and let her know that he always wanted her to join their venture.

Crazy Wills FactsShutterstock

42. The Proof is in the Tantrum

My great-grandmother left her daughter "just one dollar and not a single penny more so help me god." This was before I was born, but my grandmother (not the daughter with the dollar) said that when they all read the will her sister had a full-blown temper tantrum, and no one has heard from her since. I guess she had it coming.

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43. Prairie Home Feminism

Several generations back, a woman (along with her brothers) in our family inherited a huge sum of money from her father (oil money in Oklahoma). At the time, women were allowed to inherit property and assets if they were single, however, all of the assets would have to be transferred to her husband if she married.

She wasn't too happy about the situation and, in protest, never took a husband. She had a few "friends" over the course of her life and lived a very comfortable life until dying of old age. At which time, her estate was divided amongst all of the female descendants in the family.

Crazy Wills FactsShutterstock

44. Baa Baa Black Sheep

One client left a specific gift of $10K to one son, and left him out of the much-more-valuable estate as a way to punish bad behavior. However, by the time he passed, our client had a serious reversal of fortune. His estate was worth about $10K, so he effectively disinherited the "good" children and left the black sheep everything.

The bad kid appeared to be very poor, compared to the others, and the look of grateful surprise on the poor kid's face was almost as priceless as the shock on the others who thought they were getting rich.

Unforgettable Comments FactsShutterstock

45. First to Go, First to Settle the Dispute

I worked with trusts and estates for many years. One of my favorite clients was a widower whose wife had passed 20 years earlier. After his wife's passing, he wanted to travel the country in a motor home but was too grieved to do so. Years later his old army buddy's wife passed and they re-established their friendship during their retirement years. He finally bought the motor home he'd dreamed of and left with his buddy to travel the continent, which they did for many years.

After he passed, he left a new motor home to his buddy, but with one stipulation. The buddy had to mount a set of 6-foot longhorns on the hood of the rig before it could be his. It sounded like a Texan vs non-Texan dispute they'd had for many years. Absolutely brilliant, and seemed like an amazing friendship. I would have loved to hear their traveling adventures over the years.

Crazy Wills FactsNeedpix

46. That Thing You Get

I was a courier in Seattle and filed the will of the guy who owned the Space Needle. Yes, it's private property. There was all this interesting stuff about how the Space Needle would be administered, but what I really was interested in was that he owned a HUGE collection of Volkswagens, most of them the Volkswagen Thing.

For those who don't know, the Thing is a sort of boxy-looking Volkswagen bug. There were, I remember, 43 of these vehicles, all in their different conditions. Each of the children and grandchildren were getting a Volkswagen (and a few other older kitschy Volkswagens, like Beetles and some vans) that represented how much their grandfather had liked them.

Crazy Wills FactsWallpaper Flare

47. It’s All About Timing

My great-great-grandfather left all his money to the eldest child of his eldest grandson and arranged for it to be delivered 50 years after the last of his relatives alive at the time of his passing themselves passed on. Lucky me, I'm that descendant, but my grandmother was born right before he had passed, and she's probably going to live another 20 years, so if I make it to 90, I'll be filthy rich. Or my kids will have a nice retirement, I guess. Anyway, I always thought that was about as vindictive as you can get.

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48. Never Change

My grandfather's will had several conditions for our inheritance. Some were heartwarming, but most were strange to fully absurd. For example, my parents both had to remain left-handed. The only thing I received (or really cared about) was a 1932 Philco radio (it was the first radio I restored when I was a kid). To get it, I was required to promise that I'd keep “the old beast,” as he called it, running for as long as I owned it.

My daughter received a music box on the grounds she remains the eldest great-granddaughter (?). She also received a couple of puzzles that she had helped my grandpa with when we had visited a few times before his passing, again on the grounds that she actually “finished the darn things because he had never gotten around to it.” Actual wording from the will!

Leave it to my grandfather to give us a reason to laugh after leaving us!

Weird Flex Kids FactsShutterstock

49. Grandpa’s Archenemy

My grandfather hated his neighbor. They lived next to each other for over 20 years. I remember well my grandfather raging at every opportunity about this guy. We never saw them speak to each other. In my Grandpa's will, he left the guy $10k, a car, and golf clubs. Needless to say, as a family we were dumbstruck, until we found out the surprising reason why.

It turned out that they were good buddies from the army. When they coincidently bought homes next to each other they decided to play a long con on both of their families. They actually played golf together twice or three times per week and had a monthly poker game going for many years!

Crazy Wills FactsWallpaper Flare

50. The Car Collection of Oz

My grandfather was a Vietnam veteran who suffered from PTSD. It got worse in his later years and he would often isolate himself from the rest of the family, often hiding out in his bedroom when visitors were over. My grandmother would often tell us stories about how he had inherited a significant amount of money from his father way back when. She said that in their younger years he spent the money on luxurious dates and trips. After returning from Vietnam, he spent the rest on the house where he and my grandmother raised their children.

A couple of months before he passed, we found out that he had written a will. Even my grandmother didn't know about it. We all assumed that he wouldn't have much to leave since most of the money he had saved was being used to take care of him because he had been placed in a care facility as his PTSD worsened.

His will told of a warehouse in Township, Michigan that held a large collection of vintage cars. He said that the warehouse was passed down from his father, and he had all the documents to prove that he was the owner of some type of warehouse. His will estimated that the cars be worth an excess of two million dollars in total. The money from his collection would be split between his four children.

We had no idea this collection ever existed. It just made no sense. My father and his three brothers had all grown up in Plano, Texas. None of us had ever been to Michigan before. Even our mother couldn't recall a time of our father ever having even gone to visit Michigan. After a long debate, my father and I, the only ones who could manage to find some time off from work, agreed to fly out to Michigan to see this collection first hand.

After a few thousand dollars spent on plane tickets, hotels, etc. we finally arrived at the warehouse my grandfather owned. It was a rundown warehouse, but it was tucked away within a compound of other warehouses that seemed to be otherwise well taken care of. Finally, code in hand, my father punched the numbers into the keypad and the giant door began to rise.

What was inside is beyond words. There was absolutely nothing. There were a few homeless people that managed to sneak in through a hole in the corrugated metal around back, but there certainly was no car collection. We were able to contact a few owners of the neighboring warehouses and to their knowledge, no one and nothing had ever been inside of those warehouses in the years they had been there.

To this day we don't know what happened. We all just assume that the PTSD caused him to create some kind of fantasy in his mind. That maybe he purchased the warehouse believing it was a safe house for him if he ever needed to get out of Plano.

Crazy Wills FactsWallpaper Flare

51. 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.

Lawyers Moral Compass FactsShutterstock

Sources:  Reddit,

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