Most people think of Dr. Seuss and immediately picture a tall cat in a striped hat or a grumpy green guy ruining Christmas. But before the rhymes got really bouncy and the characters turned into neon-colored creatures, Theodor Geisel wrote something different. Something strange. In 1938, he published The 500 Hats of Bartholomew Cubbins, and honestly, it’s still one of the most unsettling, brilliant things he ever put on paper.
It isn't a rhyme. That’s the first thing that hits you. It’s prose.
The story follows a kid named Bartholomew who just wants to sell some berries in the Kingdom of Didd. He’s poor. He’s got one hat. But when King Derwin rides by and demands everyone take off their hats, Bartholomew complies, only to find another hat already on his head. Then another. And another. It’s a nightmare scenario wrapped in a fairy tale, and it reveals a side of Seuss that felt way more "Grimm’s Fairy Tale" than "Green Eggs and Ham."
The Weird History Behind the 500 Hats
Geisel didn't just pull this idea out of a vacuum. He was a collector of hats. Seriously. He had a secret closet filled with hundreds of them, and he’d often make guests wear them during dinner parties to loosen them up. The story actually started on a train ride from New England to New York. Geisel noticed a fellow passenger sitting there with a very formal, very stiff hat, and he found himself wondering what would happen if he just snatched it and threw it out the window. Would another one just appear?
That's how Bartholomew was born.
💡 You might also like: Not the Nine O'Clock News: Why the Satirical Giant Still Matters
Unlike the bright, chaotic palettes of his later work, the original illustrations for The 500 Hats of Bartholomew Cubbins are mostly black and white charcoal drawings. The only splash of color? The hats. That bright red makes the growing pile feel almost threatening. It’s a visual choice that makes the King’s escalating fury feel real. You can feel the tension in the kingdom. It’s not just a "silly" book; it’s a story about a kid who is legitimately about to be executed because of a magical glitch he can't control.
Why King Derwin is the Ultimate Seuss Villain
We talk a lot about the Grinch, but King Derwin is actually scarier. He’s a bureaucrat with absolute power. When Bartholomew can’t stop the hats from appearing, Derwin doesn't think, "Wow, a miracle!" He thinks, "This kid is disobeying me."
He brings in everyone. The Royal Hatters can’t fix it. The King’s nephews—who are total brats—try to shoot the hats off with arrows. Nothing works. It gets dark fast. Derwin eventually sentences a child to death for something that isn't his fault. If you read it today, it feels like a sharp critique of how authority figures often prioritize their own ego over logic or even human life. Geisel was always a bit of a rebel, and this was his first major shot across the bow of "the establishment."
Interestingly, this wasn't just a one-off character. King Derwin actually shows up again later in Bartholomew and the Oobleck. In that one, he’s still a jerk, proving that Seuss had a very specific vision for the Kingdom of Didd as a place where the people in charge were usually the ones causing all the problems.
📖 Related: New Movies in Theatre: What Most People Get Wrong About This Month's Picks
The Mathematical Madness of the Hat Progression
The hats don't just repeat. They evolve.
As Bartholomew gets closer to the 500th hat, they start getting more ornate. We’re talking feathers, jewels, gold lace, and silver tassels. By the time he reaches the end of the line, the hats are worth a literal fortune. This is where the story shifts from a horror-comedy into something almost mystical.
When the 500th hat finally appears, it’s so beautiful and so valuable that the King’s anger just... evaporates. He decides he’d rather have the hat than the execution. He buys the hat for 500 gold pieces, and suddenly, Bartholomew’s head is bare. It’s a weirdly "capitalist" ending for a Seuss book—the kid basically sells his way out of a beheading.
Lessons From the Kingdom of Didd
If you’re looking for a takeaway, The 500 Hats of Bartholomew Cubbins is basically a masterclass in handling a "black swan" event. Life throws things at you that make no sense. Sometimes you follow every rule, you take off the hat, and there’s still another hat.
👉 See also: A Simple Favor Blake Lively: Why Emily Nelson Is Still the Ultimate Screen Mystery
The book teaches us that:
- Logic doesn't always apply to people in power.
- Sometimes the solution to a problem is just waiting for the cycle to finish.
- Aesthetics and value can sometimes override blind rage (though maybe don't bet your life on it).
How to Revisit the Story Today
If you want to dive back into this world, don't just look for a cheap reprint. Try to find an edition that preserves the original scale of the illustrations. The "Vanguard Press" era of Seuss is different. It’s more textured.
- Compare the prose to the rhyme. Read it out loud. You'll notice Geisel’s rhythm is still there, even without the AABB rhyme scheme. He had a pulse for language that worked even in standard sentences.
- Look at the Grand Duke Wilfred. He represents the absolute worst of "nepo babies" before that was even a term. His solution to everything is violence or tantrums, which serves as a great foil to Bartholomew’s quiet persistence.
- Check out the 1943 stop-motion short. It was nominated for an Oscar! It’s a bit dated now, but it captures that eerie, surrealist vibe that the book radiates.
The beauty of The 500 Hats of Bartholomew Cubbins is that it doesn't talk down to kids. It acknowledges that the world can be unfair, magical, and terrifying all at once. It’s a reminder that even when you’re down to your last hat—or your 500th—you’ve gotta keep your head up.
To really appreciate the depth here, go back and look at the background characters in the Kingdom of Didd. Seuss packed the margins with tiny details about the townspeople’s lives that hint at a much larger, weirder world than we ever get to see. It's a foundational text for anyone who loves surrealist literature or just wants to see where the most famous children's author in history really got his start.