One last laugh… from beyond the grave.
Your last will and testament is more than a legal document—it’s a final message to the people you love (or maybe to a few people who rubbed you the wrong way). Most wills are serious, heartfelt, and practical. But every now and then, someone uses theirs to make a bold statement, stir the pot, or share one last joke.
At Paige, we believe your legacy should reflect your personality—and yes, that includes your sense of humor. If you’re looking for inspiration or just a good laugh, here are eight real-life wills that left more than just money behind.
1. Trying to Pay Off the U.K.’s National Debt
In 1928, a generous (and anonymous) Brit left his entire estate to help pay off the U.K.’s national debt. But here’s the catch: the fund can only be used once it’s large enough to wipe out the entire debt in one go.
It’s been nearly a century, and the fund now holds £350 million… not quite enough to tackle the U.K.’s £1.2 trillion debt. Still, we admire the optimism—and the comedic timing. Talk about playing the long game.
2. Shakespeare’s Second-Best Bed
When it comes to final snubs, William Shakespeare might be the king. In his will, the legendary playwright left his wife, Anne Hathaway, nothing but his “second-best bed.” The rest of his estate went to his daughters.
Was it a final insult or an inside joke between the two? Historians are still debating, but the Bard certainly knew how to exit stage left with flair.
3. The Dog Who Inherited Millions
Leona Helmsley—hotel magnate and self-proclaimed “Queen of Mean”—left $12 million to her Maltese pup, Trouble. Yes, you read that right.
She left two of her grandchildren out of the will entirely, while her dog received a luxury trust fund. While a judge eventually reduced the amount to $2 million, Trouble lived out her days in style, complete with a security detail. We’re guessing she was a very good girl.
4. Picking Heirs Out of the Phone Book
Portuguese aristocrat Luis Carlos de Noronha Cabral da Camara had no close family—or much interest in choosing heirs the traditional way. So, he picked 70 names at random from a Lisbon phone book.
Each lucky stranger received a portion of his estate. It was a literal lottery win, and a reminder that when it comes to your will, you make the rules.
5. “Please Remarry—So Someone Else Will Suffer”
Poet Heinrich Heine left everything to his wife—with one condition: she had to remarry.
Why? He cheekily wrote, “There will be at least one man to regret my death.” Not exactly romantic, but definitely memorable.
6. The Great Stork Derby
Canadian lawyer and known prankster Charles Vance Miller turned his will into a nationwide baby race. When he died in 1926, he stipulated that his estate would go to the Toronto woman who had the most children in the next 10 years.
The result? The Great Stork Derby. Four families with nine kids each split the winnings. It’s one of the strangest contests ever sparked by a will—and one that still makes estate planners chuckle.
7. No Mustaches Allowed
In 1862, Henry Budd left £200,000 to his sons—with one hairy condition: they must never grow mustaches.
Apparently, facial hair was a deal-breaker. And Budd wasn’t alone—others like Matthias Flemming even penalized mustached employees in their wills. Talk about grooming standards.
8. Houdini’s Séance Code
Famed illusionist Harry Houdini gave his wife a list of secret words before he died and asked her to hold a séance every year on Halloween. The goal? To prove communication from the beyond was possible.
For 10 years, she held séances in hopes of hearing the code. He never “called,” but it remains one of the most charming afterlife experiments in history.
A Will Can Be Whatever You Want It to Be
These laugh-out-loud examples prove that a will can be more than a list of legal instructions—it can reflect your personality, your priorities, and even your sense of humor.
At Paige, we help you build a legacy that’s entirely your own:
- Leave heartfelt messages to loved ones
- Plan how you want to be remembered
- Organize your will and documents all in one secure place
Whether your final wish is to share a private joke, fund a furry friend, or make one last unforgettable statement, your will is the perfect place to do it.
Start writing your story today. Your legacy should sound like you—even if it includes a few laughs.
Get started with Paige →
