You probably remember the rhythm. It’s got that jaunty, almost limerick-style bounce that sticks in your head for decades after you first hear it in preschool. "There was a crooked man, and he walked a crooked mile..." It sounds like a whimsical bit of nonsense about a guy with bad posture living in a lopsided house. But if you look at the history of British nursery rhymes, nothing is ever just about a guy with a bent spine. Most of these rhymes are actually political cartoons disguised as children's songs so the authors wouldn't get thrown in the Tower of London for treason.
The there was a crooked man rhyme is basically a 400-year-old diss track.
While it feels like a fever dream about a crooked cat and a crooked mouse, it’s widely believed by historians to be a very specific jab at a Scottish general named Sir Alexander Leslie. He wasn't literally "crooked" in the sense of having a physical deformity, but he was the face of a massive political and religious "crookedness" that nearly tore the UK apart.
Where the crookedness actually began
Let’s look at the lyrics first. You’ve got the man, the mile, the sixpence, the stile, the cat, the mouse, and the house. It feels cohesive. It feels like a little world.
The rhyme first showed up in print in James Orchard Halliwell’s 1842 collection, The Nursery Rhymes of England. But like most oral traditions, it was floating around long before that. The "crooked mile" isn't just a distance; it’s a reference to the border between England and Scotland. During the reign of King Charles I, things got messy. Really messy. The king wanted everyone to use the same prayer book, and the Scots—specifically the Covenanters—were absolutely not having it.
Sir Alexander Leslie signed a covenant to defend Scottish religious freedom. This is the "crooked man" of the legend. He led the Scottish army against the King's forces. The "sixpence" mentioned in the verse represents the agreement or the "crooked" deal made between the Scots and the English Parliament to take down the King.
Honestly, it’s kind of wild that we teach this to toddlers.
Imagine explaining the National Covenant of 1638 to a three-year-old. You wouldn't. So, the folk singers of the day wrapped the political tension in a metaphor about a guy who couldn't walk straight. It’s genius, really. It kept the sentiment alive without getting the singer executed for sedition.
The Scottish Connection and the Covenanters
If you go to Lavenham in Suffolk, England, you’ll see plenty of "crooked" houses. They’re famous for it. The timber frames dried unevenly, leaving the buildings looking like they’re melting. Many people claim this is the origin of the rhyme. They point to the "crooked house" mentioned at the end of the poem and say, "Look! It's right there!"
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It’s a nice story for tourism.
But the historical weight usually leans toward the Scottish General Leslie. The "crooked stile" represents the border between the two countries. The "crooked cat" and "crooked mouse" are often interpreted as the various factions—the Royalists and the Parliamentarians—who lived in uneasy, "crooked" harmony after the fighting stopped. It was a peace that wasn't really a peace. Everything was slightly off-kilter.
Why the rhythm matters more than the words
Nursery rhymes use a specific meter. This one is mostly trochaic. It’s catchy.
There was a / crooked / man...
This specific structure makes it incredibly easy to memorize. That’s why the there was a crooked man rhyme survived through the 1700s and 1800s without being written down in every household. It stayed in the collective ear.
You’ve probably seen the dark variations, too. Horror movies love this rhyme. From The Conjuring universe to various creepy creepypastas, the "Crooked Man" has been turned into a spindly, terrifying monster. Why? Because there’s something inherently unsettling about the word "crooked." It implies that something that should be straight and right has been warped.
Psychologically, we find it creepy.
The poem suggests a world where nothing is quite right. The cat doesn't catch the mouse to eat it; they just live together in a crooked state. It’s an internal consistency of wrongness. That’s what makes it a goldmine for horror directors, even if the original 17th-century meaning was just about a guy named Alexander and a religious treaty.
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Comparing the interpretations
Let’s be real: we will never have a 100% confirmed receipt from a 17th-century writer saying, "Hey, I wrote this about General Leslie." History doesn't work that way. We have to look at the clues.
- The Political Theory: This is the one favored by academics like Iona and Peter Opie, the legendary duo who studied nursery rhymes for decades. They looked at the timing and the geography. It fits the Covenanter movement perfectly.
- The Lavenham Theory: This is the local folklore. Lavenham was a wealthy wool town. When the wool trade hit a slump, the builders used green timber. The houses warped. It’s a literal interpretation. It’s charming, but maybe a bit too literal.
- The Moral Lesson: Some Victorian-era parents used it as a cautionary tale. If you are "crooked" in your heart (dishonest), your whole life will become crooked. Your house, your pets, your money—all of it will reflect your character.
The political theory is the most robust. It connects the rhyme to a specific "mile" (the border) and a specific "sixpence" (the payment to the Scottish army).
The Sixpence and the Stile: Symbols of a Deal
What about that sixpence?
In the rhyme, he finds it on a stile. A stile is a set of steps used to get over a fence or a wall. In the political context, this represents the "jump" across the border. The sixpence is often cited as the 1640 Treaty of Ripon. The King had to pay the Scottish army a massive sum of money every day just to stay put and not invade further into England.
It was a "crooked" deal because it was basically extortion.
The Scots were sitting on the "stile" (the border), holding a "crooked" sixpence (the King's forced payments). When you look at it through that lens, the whimsical nature of the poem evaporates. It’s actually a poem about a high-stakes military standoff that eventually led to the English Civil War and the execution of King Charles I.
Kind of heavy for a bedtime story.
But that’s the beauty of the there was a crooked man rhyme. It’s a layer cake. The bottom layer is a brutal civil war. The middle layer is a catchy folk song. The top layer is a cute story about a guy with a funny walk. Most of us just eat the top layer and never realize what’s underneath.
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Does it still matter today?
You might wonder why we still care.
Apart from the SEO value of people searching for their childhood memories, these rhymes are the DNA of English literature. They teach us about irony. They teach us about subtext. When you realize that "Ring Around the Rosie" might be about the plague (though that's actually debated by some folklorists) or that "Humpty Dumpty" was likely a cannon, you start looking at language differently.
You start realizing that words can hide things.
The "crooked man" is a reminder that even when things seem "all together" in their "little crooked house," they might be fundamentally broken. It’s a very human sentiment. We all have those moments where our lives feel a bit warped, where we’re just trying to balance a sixpence on a fence.
Actionable Takeaways for History Buffs and Parents
If you're looking to dive deeper or share this with others, here is how you can actually use this information without being a boring textbook.
- Visit the "Crooked House": If you are ever in the UK, go to Lavenham. Even if the Leslie theory is more historically accurate, the houses in Lavenham are a physical manifestation of the rhyme that you can actually see and touch. It makes the history "real" for kids.
- Check the Source Material: Pick up a copy of The Oxford Dictionary of Nursery Rhymes by Peter and Iona Opie. It is the gold standard. If you want to know if a rhyme is about a king, a plague, or just a random cat, that's where you find the truth.
- Teach the Subtext: When reading to children, you don't have to explain the English Civil War, but you can talk about how "crooked" doesn't always mean "broken." It can mean unique. Or it can mean something is being hidden. It’s a great jumping-off point for talking about honesty and how things aren't always what they seem.
- Look for Variations: There are dozens of versions of this rhyme. Some mention a "crooked penny," others a "crooked sixpence." Compare them. Usually, the change in currency tells you when and where that specific version of the rhyme became popular.
The there was a crooked man rhyme isn't going anywhere. It’s too catchy to die. But now, the next time you hear it, you won't just see a cartoon character. You'll see Sir Alexander Leslie, a border dispute, and a crooked little piece of British history that managed to survive by hiding in plain sight.
For those interested in the linguistic evolution, notice how the word "crooked" is used as a repetitive anchor. In early English poetry, this kind of repetition wasn't just for kids; it was a mnemonic device for the illiterate. It ensured that the message—and the mockery of the Scottish General—would be remembered by everyone from the tavern to the nursery.
History is rarely straight. It’s almost always a bit crooked.
Next Steps for Exploration
To truly grasp the era that birthed this rhyme, your best bet is to look into the Bishops' Wars of 1639 and 1640. This is the specific conflict where Sir Alexander Leslie made his mark. Understanding the tension between the Covenanters and the Royalists provides the "why" behind the "crooked" metaphor. Additionally, researching the architectural history of Tudor timber-framing will give you the context for why "crooked houses" were so common in the 17th century, providing the visual backdrop for the rhyme's imagery. If you want to see the rhyme in a modern context, look into its use in the film The Conjuring 2, which explores the darker, psychological side of the "warped" imagery.