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.