People often believe that a will is a simple document—a way to pass down wealth and possessions to loved ones. But sometimes, a last will and testament can be a final act of revenge, a shocking confession, or a completely unexpected surprise.
Over the years, people have written some of the most bizarre, heartbreaking, and even hilarious things in their wills, leaving their families speechless.
Some people draft their wills while they are still healthy, carefully planning their legacy. Others only consider it when a doctor gives them bad news. While many divide their assets among close family members, others take a different route—one that no one sees coming.
Here are some of the most unusual, jaw-dropping stories shared by people on Reddit. These wills didn’t just distribute wealth—they uncovered secrets, played tricks, and changed lives in ways no one could have predicted.
1. A Goldfish With a Trust Fund?
u/scarlett_pimpernel: “As a solicitor, I’ve seen my fair share of strange wills, but this one stands out. A woman came to me and insisted on setting up a trust fund of £100,000 for her pet goldfish.”
Confused, I asked, “Is this a rare or special kind of fish?”
She shook her head. “No, just a regular goldfish.”
She explained that after her death, the fish was to be cared for by a local dog walker and fed fresh avocado every day. She was completely serious. I made sure to draft her wishes exactly as she requested, though I couldn’t help but wonder if the dog walker knew what they were signing up for.
2. A Hidden Daughter
u/scarlett_pimpernel: “One of the most shocking wills I ever worked on involved a woman who had a secret daughter. No one—not her husband, not her other children—knew about this girl.”
She told me, “I want to leave her some money and a collection of photographs, but under no circumstances should my family find out.”
I hesitated. “Even your husband doesn’t know?”
She gave a small, sad smile. “No. And I don’t want him to. This is between me and her.”
I drafted the will as requested, but I couldn’t stop thinking about the moment when the family would discover the truth. That would be an unforgettable conversation.
3. The Bus Driver’s Inheritance
u/mommy5dearest: “I worked at an attorney’s office where an elderly woman left her house and all her belongings to her bus driver.”
Why? Because he was kind to her.
“He always helped me on and off the bus,” she explained, “and he asked how my day was. That meant the world to me.”
Her family was completely blindsided when they found out. We braced ourselves for a legal battle, but the will was airtight. She had been of sound mind when she signed it, and she knew exactly what she was doing. The bus driver had no idea she had planned to do this. Imagine his shock when he found out he now owned a house simply for being kind.
4. The Ultimate Prank From Beyond the Grave
u/WanderCold: “When I was in my twenties, I had to write a will because of my job’s health insurance policy. I decided to have a little fun with it.”
His will contained this peculiar clause: “I wish to be buried in a coffin equipped with a spring-loaded mechanism, so that if anyone ever tries to open it in the future, they will get a shocking surprise.”
His lawyer read the request and raised an eyebrow. “Are you serious?”
“Absolutely,” he said, grinning. “If that’s too expensive, just cremate me and scatter my ashes in a specific location.”
One can only hope future archaeologists are prepared for the scare of their lives.
5. A Horse’s Lucky Escape
u/gabberrella24: “I work in probate law, and one of the strangest wills I’ve seen involved a woman who wanted her beloved horse euthanized upon her death.”
She instructed that the horse should be cremated and its ashes scattered with hers.
Fortunately for the horse, there was a loophole. The horse she had named in the will had already passed away. By the time she died, she had a new horse, but because her will named the old one specifically, the new horse got to live out its days on a peaceful farm instead.
6. The Baby Boom Contest
u/PirateRobotNinjaofDe: “A wealthy lawyer left his fortune to whichever woman in Toronto had the most children a certain number of years after his death.”
A legal baby-making contest?
Indeed. By the time the deadline arrived, the winner had ten children and walked away with a life-changing sum of money. Talk about an unusual way to distribute wealth.
7. The Power of a Ridiculous Tie
u/snoboreddotcom: “After my grandfather passed away, my grandmother handed me a navy-blue tie with bright pink elephants on it. It looked ridiculous.”
Confused, I asked, “Why did he want me to have this?”
She smiled. “He wore it in business meetings to intimidate people. He believed that someone who wears such a ridiculous tie clearly doesn’t care what others think—and that scares people. He wanted you to have it so you could do the same.”
And so, I did.
8. Unusual Conditions
u/ALighterShadeOfPale: “One woman put a condition in her will that her son could only receive his inheritance after he went to the dentist. Her other son had to lose seventy pounds to get his share.”
A different woman insisted that her cats be cremated with her, but the law didn’t allow human and animal remains to be cremated together. She settled for a compromise: the cats would be cremated separately, then their ashes would be combined with hers before burial.
9. The Never-Ending Will
u/ALighterShadeOfPale: “Wills are usually about ten pages long. But one woman wrote a 56-page will, detailing who should get every single item she owned.”
She didn’t just leave her house and savings to people—she listed items like a wooden ladle, a toilet paper holder, and even a magazine basket, carefully naming who should receive each one.
Talk about thorough planning.
10. A Grave Secret
u/ALighterShadeOfPale: “One woman insisted that she be buried on her small rural property next to her husband. The problem? That’s completely illegal.”
When her lawyer pointed this out, she simply smiled. “Oh, don’t worry. He’s already there.”
Considering he had passed only five or six years prior, this raised more than a few questions.
11. Some Good People
There was a man who had one final wish before he passed away. In his will, he asked that his family go to the zoo immediately after his burial—on the same day.
“I don’t want tears and sorrow,” he had written. “I want my loved ones to celebrate life, even as mine ends.”
The thought of it was heartwarming. While most wills distribute money or possessions, this man simply wanted his family to find joy, even in their grief.
Aside from that, we often work with people from a particular religious community. Many of them leave most of their wealth—sometimes as much as 90%—to their church instead of their families. To them, faith and devotion mean more than money, and their final act is one of giving back.
12. The Elvis Impersonator
I’m not a lawyer, but I do have a story about my rich uncle. He wasn’t exactly the warmest guy—he visited us maybe once every ten years.
The last time he showed up, he took us out to Denny’s. That was it. No grand gifts, no heartfelt words. Just pancakes and eggs at a cheap diner.
He lived a lonely life. His wife had struggled with substance abuse, and that was because of him. When she passed away, he became even more isolated.
So when he finally died, we were stunned to learn who inherited everything. His entire estate—every penny—went to an Elvis impersonator.
Not a relative. Not a charity. An Elvis impersonator.
To this day, we have no idea why. Maybe Elvis meant something special to him, or maybe he just wanted to go out with a little Vegas-style flair. Either way, we were left shaking our heads.
13. The Only Beneficiary
I used to work at a bank in the estate department, managing multi-million-dollar trust accounts. One case still haunts me.
It was a huge trust fund, meant for a single beneficiary—the deceased man’s son. Everything seemed normal, until I learned the truth: The son was responsible for his parents’ deaths.
He had pleaded insanity and was locked up in a mental hospital.
Once a year, like clockwork, he would call the bank. His request? A mere $50 from his massive fortune, just enough to buy chips and gum at the hospital commissary.
The strangest part? He was always polite. But his voice sounded distant, like he was calling from far away—even though I knew he wasn’t.
14. They Wanted to Take Revenge
Last week, I handled a will that was pure, calculated revenge.
The parents were incredibly wealthy. They had millions in artwork and cash, and they left it all to various charities and distant friends. But their kids?
They got the family cats.
It turns out the kids had given their parents those cats to keep them company in old age. The parents absolutely hated them, but the kids refused to take them back.
So in one final, petty move, the parents made sure their children would take care of the cats for the rest of their lives.
15. He Wanted to Give Them Something
My great uncle had a long, bitter battle with the City Council. They tried—twice—to take his land to build a new water treatment plant.
He fought back and won both times. But when he passed, he left them something in his will.
“To the City Council,” it read, “I bequeath the full contents of my outhouse.”
As a final joke, his kids boxed up all the books and magazines from the outhouse and dropped them off at City Hall. Petty? Maybe. But hilarious? Absolutely.
16. The Man Was Clueless
I work for a will-writing specialist in the UK, and one case still surprises me.
An elderly woman left almost everything—her money, her estate—to her regular taxi driver.
Not only that, but she made him the executor of her will.
The man had no idea. When we contacted him, he didn’t even know she had passed away. Meanwhile, the woman’s lifelong friend, who had been named in her previous wills, was completely shocked. She contested the will, but in the end, it stood.
She did get something—a legacy of £5,000. But judging by her reaction, that wasn’t nearly enough to soothe her anger.
One thing I’ve learned in this business? It doesn’t take much money to tear a family apart. Sometimes, even a few hundred pounds can cause chaos.
17. Hidden Fortune
My grandmother lived in a run-down old trailer. Dirt poor. At least, that’s what we thought.
My husband, though? He was convinced she had a secret fortune hidden away.
“Sugar,” he told me, rubbing his hands together on the day of the will reading, “we’re about to be rolling in dough.”
The lawyer called his name. “You must be the husband,” he said.
“That’s me! Is there a problem?”
“Not at all. Your grandmother’s will states that she did, indeed, have a hidden fortune. However, you can only inherit it if you fulfill three conditions. If you fail, the entire estate goes to the local animal shelter.”
My husband leaned in, eager to hear the terms.
“First, you must live in her old trailer for one full year—no modern upgrades, no outside help. Second, you must volunteer at the animal shelter every weekend for two years. And lastly, you must write an essay on the value of humility and compassion, which will be read publicly at the shelter’s annual fundraiser.”
My husband’s smile disappeared. His face went pale.
Grandma may have passed on, but she had just delivered the lesson of a lifetime—from beyond the grave.
These stories prove one thing: A will isn’t just about money. A few words on a piece of paper can change lives forever—for better or worse.
