10 Weird Sentences in The English Language

English is weird—even experts in the language agree. Though a sentence can look and sound bizarre, it is probably still grammatically accurate.

What’s the weirdest, most tangled English sentence you’ve ever encountered? Chances are, there’s plenty more where that came from.

Weirdest Sentences

A lot of sentences can boggle the mind due to the complexities of grammar, different emphasis on words, syntactic ambiguity, punctuation, homophones, and homographs. Below are just a few of these confusing, and often hilarious gems of the English language.

1. Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.

Perhaps the most famous of them all, this sentence might look like nonsense but it still makes sense grammatically. Here, the word “buffalo” is being used with three different meanings:

1. The animal (A herd of buffalo wandered across the plains.)
2. The city (She was originally from Buffalo, New York.)
3. A verb meaning “to bully or baffle” (She managed to buffalo her opponent during the debate.)

So the sentence above can be understood as “Buffalo from Buffalo who are buffaloed by other buffalos from Buffalo also buffalo other buffalos from Buffalo.” 

Other, lesser-known sentences that play on a word’s triple meanings are:

• Will, will Will will Will Will’s will? (Someone’s asking Will 1 if Will 2 plans on giving Will 3 his will.)
• Police police Police police police police Police police. (Policemen from the city of Police who are policed by other policemen from Police also Police other policemen from Police. )

2. One morning I shot an elephant in my pajamas. How he got into my pajamas I’ll never know.

Groucho Marx’s famous joke doesn’t make sense when you first read or hear it. It’s only after a few tries that you are able to group the words into understandable clauses.

Most people would default to understanding the first sentence as the speaker being in his pajamas and shooting an elephant. Only after reading the second sentence do you understand it’s the elephant wearing the pajamas, not him.

3. A rough-coated, dough-faced, thoughtful ploughman strode through the streets of Scarborough; after falling into a slough, he coughed and hiccoughed.

This sentence is a phonetic play on -ough, which can have different pronunciations depending on use. From first to last, the -ough words in this sentence are pronounced: “uff,” “oh,” “auh,” “ow,” “uh,” “oo,” “off,” and “uhp.”

It points out how the pronunciation of similarly spelled words can be hard to deduce when only looking at them.

4. The rat the cat the dog chased killed ate the malt.

People typically don’t have problems with deciphering clauses within a sentence. However, the more clauses you add, the harder it is to keep track of what a sentence means.

The rat ate the malt. The cat then ate the rat. That cat was chased by a dog. While this is grammatically correct, it doesn’t sound good at all. A clearer sentence structure would be: The cat that the dog chased had killed the rat who ate the malt.

5. Rose rose to put rose roes on her rows of roses.

Here’s a sentence that doesn’t just deal with homographs but also homophones. Here’s a breakdown of it:

Rose (a woman) rose (the action of getting up) to put rose  (the color) roes (the fish eggs) on her rows (a series of things arranged in a line) of roses (the flower).

A less confusing version would be: A woman named Rose stood up and put rose-colored fertilizer on her roses, which grew in a row.

6. This exceeding trifling witling, considering ranting criticizing concerning adopting fitting wording being exhibiting transcending learning, was displaying, notwithstanding ridiculing, surpassing boasting swelling reasoning, respecting correcting erring writing, and touching detecting deceiving arguing during debating.

Depending on its usage, “-ing” can turn a word into a noun, a verb, or an adjective. It’s also one of the most versatile affixes (a string of letters attached to a word to form a new word or word form) in the English language you can use.

This particular example is found in a 19th-century English grammar guide and demonstrates just how creative you can get with the “-ing” suffix. While the sentence looks intimidating, it’s simply saying that:

This individual, despite using elaborate language to demonstrate knowledge and appear superior, is mocked for their superficial reasoning and deceptive arguments. 

7. Read rhymes with lead, and read rhymes with lead, but read and lead don’t rhyme, and neither do read and lead.

This is another example that words can look the same but not are not necessarily pronounced the same way. Try to read the above sentence like this instead: Red rhymes with led, and reed rhymes with leed, but red and leed don’t rhyme, and neither do led and reed.

8. I do not know where family doctors acquired illegibly perplexing handwriting; nevertheless, extraordinary pharmaceutical intellectuality, counterbalancing indecipherability, transcendentalizes intercommunications’ incomprehensibleness.

Just for fun, recreational linguist Dmitri Borgmann came up with this genius of a sentence. It might sound like gibberish but it is perfectly, grammatically correct. Not only that, but the next word is always one letter longer than the last. 

Here’s a more simplified version of this sentence: I don’t know where family doctors learned to write so that no one can read it. Somehow, their intelligence and their talent for poor handwriting are so perfectly matched that it perplexes me.

9. I never said she stole my money.

At first glance, there doesn’t seem to be anything weird with this sentence. But when you start emphasizing different words at a time, its meaning changes entirely. Plenty of other sentences are this way, but this one’s the most popular by far.

• I never said she stole my money. (Someone else said it.)
• I never said she stole my money. (I never ever said that.)
• I never said she stole my money. (I might have hinted at it but never actually said it.)
• I never said she stole my money. (Someone else did.)
• I never said she stole my money. (But she did do something else with it.)
• I never said she stole my money. (It was someone else’s money she stole.)
• I never said she stole my money. (She stole something else.)

10. That that is is that that is not is not is that it it is.

This sentence is often used to demonstrate the importance of proper punctuation. It can be understood as any four particular sequences depending on where you add punctuation.

However, let’s focus on its most popular interpretation: “That that is, is. That that is not, is not. Is that it? It is”. 

Once properly punctuated, its meaning becomes clear. Existing things exist. Non-existent things don’t exist. Is that the truth? Yes, it is.

Wacky Sentences

Weird but grammatically accurate sentences can be found in almost every text. Sometimes they’re made by inexperienced writers or those who are still learning the language.

In the rare chance that someone’s doing it purposefully, it’s usually because they want to catch their audience’s attention, induce a specific emotion, or convey something complex. If so, there’s a ton of fun to be had in deciphering their meaning. 

What is the weirdest sentence you’ve ever encountered? Share your experiences in the comments below!

If you enjoyed this post, then you might also like:

• What are Homographs? Definition and Examples
• Polyptoton: Definition, Examples, and Related Terms
• The Garden Path Sentence: Getting Rid of Sentence Ambiguity