Death is a pretty touchy subject. Throw in lots of money and some tense relationships and it becomes a very interesting subject as well.

These 23 AskReddit users share some of the craziest things they have witnessed in wills.

1. Best diss ever

“To my wife, I leave her lover and the knowledge that I was never the fool she thought me. To my son I leave the pleasure of working for a living – for 25 years, he thought the pleasure was all mine.” — Best diss ever. Was in my Wills & Trusts book in law school as an example of people talking smack in their wills (you’re supposed to discourage them as lawyers from doing so)

2. “Jane, bail your uncle out of jail, please.”

“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 leave all of my monetary assets, save $5000 and my best gun which I leave to my son Bill, on the condition that he beats John bloody during the time between my funeral and my burial. Jane, bail your uncle out of jail, please.”

Other than names, this is the exact wording of a great uncle’s will (part of it anyway. At age nine Jane told her mother that John had molested her and her mother told her she deserved it for being promiscuous. So Great-Uncle took Jane in and raised her, and his two kids got exactly what it says. (His son also got a truck and technically a house, although he only kept it until Jane was a legal adult and could afford the tax on it. Bill got full custody of Jane when his father died and he put every penny of her money into a trust fund to mature until she was 25 because he felt like his sister would try to get the money, he was right.)

And in case anyone wondered, yes Bill got his five grand. He didn’t get arrested though because John had a warrant on him so they didn’t dare call the cops. Bill did kindly inform the police of his whereabouts a few weeks later.

3. “Manure spreader”

Lawyer here. I once amended a will for a doctor in which he disinherited his son by removing everything he had intended to bequeath and replacing 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 die and his son will have essentially be told to “eat crap”.

4. But which is better?

Best will story I personally know of:

The Father had a valuable antique Grandfather Clock, he also had 2 daughters. His solution:

If I die on an even day, daughter A gets the clock, an odd day and Daughter B gets it.

The Daughter who did not get the clock got an equivalent cash award based on the value of the clock.

I know of the event because I had to service the clock several times over the years.

5. Rock solid

We had a client itemize his rock collection in his will, including directions that certain rocks be deposited in certain rivers across Canada.

6. Whoops

My father in law was an accountant for some rather wealthy people. One of them was asking him to assist with writing up his will worth millions. The final addition he suggested was that if the children contested it, they get nothing.

They contested it, for years!

7. Equal parts

We had a client who was a widowed farmer who owned several heavy pieces of equipment (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 his daughter, he was asked why since these equipment were essential to the farm. He said that the farm was to go to his kids equally but his girl needed to know he always wanted her to join their venture and dispel her notions of alienation because she was a girl.

8. “An unpleasant name”

It’s very rare to read a will out loud. That’s mostly in the movies. Normally I just make extra copies and pass them out to whoever in the family wants to read it.

Though the most unusual thing in a will I saw was man leaving a good chunk of money for his mistress that his wife knew nothing about. It was interesting to see sadness and anger fighting to win in the wife. She finally laughed while calling him an unpleasant name.

9. Rude

A friend of mine was adopted at birth. When her mom died, the will gave half the estate to her ‘two natural daughters’. My friend got nothing.

What the heck.

10. Mr. Bobo

I was working as a legal secretary and had to leave someone’s cats to various people (fine) but I also had to leave money in the cats’ name to various organizations. One of them was named Mr. Bobo. I enjoyed it thoroughly.

11. No idea

A woman came in after her mother’s funeral with some correspondence from the company I work for (insurance). She was worried there was a bill she needed to pay and was coming to tell us her mom had died. 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…how she missed her but just was run ragged and she hadn’t taken a vacation in forever. I realized 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 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.

12. She had it coming

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 heard from her since. I guess she had it coming.

13. Awkward

In my trusts & estates class in law school, we read a case about a man who left everything to his wife, but only if she got his body stuffed and left it on the living room couch forever.

Luckily for her, the court invalidated that part of the husband’s will. IIRC, part of the reasoning was that it would make it impossible for her to date/remarry if she had her husband’s creepy dead body glaring at anyone who came to see her.

14. Jokes on you

My grandfather hated his neighbor. They lived next to each other for 20+ years. I remember well my grandfather raging at every opportunity about this guy. We never saw them speak to each other.

In Grandpa’s will, he left the guy $10k, a car and golf clubs. We were dumbstruck.

Turns out they were good buddies from the Army. When they coincidently bought homes next to each other they decided to play a long scam with both their families. They actually played golf together 2-3 times per week and had a monthly poker game for years.

15. Liquidation

When my dad’s mother died, her will stipulated that everything was to be liquidated and the money distributed equally among her children and grandchildren. Fine, but literally everything had to be sold. There were family heirlooms, jewelry, things my grandfather (a carpenter) had made. So many sentimental family things that my father and his siblings badly wanted, but it all had to be sold. They all went to the auction to try to buy some of the more sentimental items but weren’t always successful. It was heartbreaking and I’m not sure what made my grandmother think it would be a good idea. Nobody wanted the money, they wanted her wedding ring and the clocks my grandfather had made and all that.

16. I don’t care

I used to work for an accountant and we used to make wills as well.

An old man probably around 70 left all his money to his mistress while his wife only got the goldfish.

I had to tell him that if his wife contested it she would most definitely win, he said he didn’t care.

17. Little dog

When my great uncle died he left his beloved dog to his longtime girlfriend. All of his money went into a pet trust for said dog, which turned out to be quite a large sum of money. His 2 kids got nothing. As far as I know, he didn’t have a bad relationship with them or anything, he just thought the world of his little dog.

18. Beloved cat ashes

One summer I worked as an administrative assistant to a lawyer who worked in wills and estates.

Most of it was the usual petty arguing about percentages of money, but one couple was deeply concerned about which of their children would receive the urn with the ashes of the family’s long-deceased cat. “Wouldn’t want to play favorites.”

19. Loaded

One of my college buddy’s dad died from cancer in our second year. It wasn’t a sudden death, he had been battling it for a couple years. When my friend came back to school, he casually mentioned that his dad left him and his sister $7 million each. Turns out, his dad had hit the lottery before my friend was born, invested and put all the money away to help pay for college and high school. He knew his dad won the lottery but wasn’t aware of how much he won. His mom got a nice chunk of change also. He grew up thinking they were just ordinary middle-class family. We had a glorious third and fourth year of college, thanks to my loaded friend.

20. Lighten the mood

I sat my wife down to have ‘the talk’ because I was getting ready to deploy to Iraq. This was during the incredible sectarian violence, and I wanted to make sure she knew everything to do in case I died. She’s never serious. Ever. But I wanted her to be serious for this discussion because it was damned 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?”

Look, she’s not trying to be a jerk right? It’s not like she’s just dying for the money. She wants to know the logistics of it. I’m sitting here thinking when she says, “So do they put 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.

I have it written into the will that if I’m killed in action, I want the $400K to be given to her with a gigantic lottery check. Have base photo bring several folks over, shoot like the paparazzi as she stands on a stage, and do it. LOL.

21. Source of butter?

An ancestor of mine in the rural UK in the 1700s died and 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?!

22. Lesson learned

My wife and I went to a lawyer to have our wills drafted. The lawyer told us of a client he had that had a great deal of money. His kids were fighting over it before he was dead. The man liked the monkey exhibit and the local zoo, he liked to just watch them all the time. When he died the lawyer had to tell his family he willed all of his money and estates to the zoo for the monkey exhibits. He now has a bench dedicated to his honor at one of the local zoos. He said they were livid and tried to fight. The lesson is to not be petty and greedy love your family unconditionally.

23. Serves them right

Years ago, worked in a retirement community. Older man we knew was gay developed a late in life relationship and moved into the community with his gay lover. He was a Korea vet, multiple honors, a wall of medals. He was also a bit of a jerk most days, but he had moments over a meal his stories were fantastic.

His children over three years never once visited him. He had a heart attack and knew he was going to die. His children showed up but demanded his lover leave for 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.

He left each of his two kids a pail of coal ash, to be deducted from his estate, had his estate pay for his lovers plot to be next to him and his wife, and in his long letter that his kids, if they visited him in his death, would be reminded of why they didn’t visit why he was alive.

It was, frankly awesome hearing his kids blow up about it.

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