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These Are the Weirdest Sentences in the English Language

English Grammar
These Are the Weirdest Sentences in the English Language
on July, 20 2017

English grammar is weird. The strange, sometimes inconsistent rules of English grammar have produced sentences that have boggled the mind for generations.

You’ve probably heard of the crown gem of English grammar: Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo. The sentence makes grammatical sense because ‘Buffalo’ can have three meanings, which can perform a variety of syntactical roles.

  • buffalo: a hooved animal (noun); also commonly used to refer to bison, although bison are not really buffalo--colonists mislabeled them, just like they did ‘Indians’
  • Buffalo: a city in New York (noun; or modifier, describing something from Buffalo, as in Buffalo wings)
  • buffalo: to bamboozle (verb)

So the sentence means that bison from New York (Buffalo buffalo) who other bison from New York bamboozle (Buffalo buffalo buffalo), bamboozle bison from New York (buffalo Buffalo buffalo). Now say it three times fast!

Since you’ve got time to kill, and you love English grammar as much as we do, let’s go through some of the English grammar’s strangest, funniest, and most hilariously baffling sentences. See how many of them you can figure out on your own!

Related Post: Check Out These 7 Hilarious Translation Fails


Garden Path Sentences

These are sentences with deceptive English grammar. They lead you ‘down the garden path’ until you have to retrace your steps and reinterpret the meaning of the words at the beginning. The sentences make sense according to English grammar rules, but sometimes it takes a double take to get their meaning.

The old man the boat.

This Hemingwayesque morsel tricks you into reading ‘the elderly male’ and then leaves you hanging with ‘the boat.’ Huh?

The gimmick here is that ‘the old’ refers to ‘elderly people,’ and ‘man’ is a verb, meaning ‘to staff.’ Read it again, as ‘Elderly people are staffing the boat.’

This sentence has been used in psycholinguistic research and in testing AI. So if you ever want definitive proof of why human translators rule, try running this through your machine translator!

The horse raced past the barn fell down.

Can’t figure this one out? Here’s a hint: it’s in the passive voice.

Here’s another: the barn didn’t fall down.

Got it? ‘[The horse that was raced past the barn] [fell down.]’

The complex houses married and single soldiers and their families.

What first sounds like complicated dwelling spaces changes form when you realize that ’complex’ is the noun and ‘houses’ is the verb. ‘Married’ is an adjective, not a past tense verb, which modifies ‘soldiers.’

Married soldiers, single soldiers, and their families are all housed in the complex.

If you find your eyes skipping like a record needle on sentences like these, that’s normal. Scientists have found that rapid, erratic eye movement results from figuring out a garden path sentence.

Time flies like an arrow; fruit flies like a banana


Still Life, Fast Moving by Salvador Dalí, 1956

This chuckler is attributed to German linguist Anthony Oettinger in the 1960s, and circulated by numerous writers since then. A similar joke appeared in Boy’s Life magazine thirty years earlier:

Scoutmaster: Time flies.

Smart Tenderfoot: You can't. They go too fast.

It also inspired the following ode by Edison B. Schroeder in 1966:

Time Flies Like an Arrow
An Ode to Oettinger

Now, thin fruit flies like thunderstorms
And thin farm boys like farm girls narrow;
And tax firm men like fat tax forms -
But time flies like an arrow.

When tax forms tax all firm men’s souls,
While farm girls slim their boyfriends’ flanks;
That’s when the murd’rous thunder rolls -
And thins the fruit flies ranks.

Like tossed bananas in the skies,
The thin fruit flies like common yarrow;
Then's the time to time the time flies -
Like the time flies like an arrow.

Related Post: 20 Awesome British Slang Terms You Should Learn Today


Syntactical Ambiguity

Syntactically ambiguous sentences conform to the rules of English grammar, but can change their meaning. This happens when it’s unclear, for example, to which noun a modifier or modifying phrase refers. Sometimes they change meaning based on the presence of homonyms and polysemes, or the absence of an Oxford comma, as in the following gem:

This book is dedicated to my parents, Ayn Rand and God.

That’s sure to be an interesting read. Hopefully it’s a biography. Or would you put it back on the shelf if the Oxford comma were in place?

I'm glad I'm a man, and so is Lola.

The Kinks sang this in their 1970 hit “Lola.” Ray Davies penned the lyric to be deliberately ambiguous. Is Lola glad that the singer is a man? Or is Lola also a man? Both interpretations work for English grammar, and both are meaningful in the context of the song.

The Kinks

The Kinks, 1965

John saw the man on the mountain with a telescope.

WHO HAS THE TELESCOPE THOUGH?! THERE CAN ONLY BE ONE! We must resign ourselves to the agony of perpetual suspense.

A woman without her man is nothing.

This comes from the viral wisdom of social media. The story goes that when asked to punctuate this sentence, the males in the class placed a couple of commas thusly:

A woman, without her man, is nothing.

But the women in the class used a colon and a comma to tell a different story:

A woman: without her, man is nothing.

James while John had had had had had had had had had had had a better effect on the teacher.

Okay, bear with. This one takes some setup: an English grammar teacher asks James and John to describe a man who suffered a cold.

John writes The man had a cold. The teacher marks it wrong. James writes The man had had a cold. The teacher marks it correct. James’ answer had a better effect on the English grammar teacher, so:

James, while John had had "had", had had "had had"; "had had" had had a better effect on the teacher.

That that is is that that is not is not is that it it is

Although not a correct sentence in itself, this word sequence demonstrates the way punctuation can alter the meaning of English grammar. This sequence can have three meanings, depending on where the punctuation falls:

That that is, is. That that is not, is not. Is that it? It is.

That that is, is that that is. Not is not. Is that it? It is.

That that is, is that that is not. Is not "is that" it? It is.

Related Post: These Hilarious Subtitling Errors Are Too Good to Be Missed!


Crash Blossoms

Crash Blossoms are headlines that have multiple (usually accidental) meanings. The best of these English grammar oddities impact the reader first with a meaning that makes linguistic sense, but is absurd. The name comes from the following headline:

Violinist linked to JAL crash blossoms

Naturally, the intended meaning is that the violinist blossoms. But the headline left a number of readers wondering what the heck ‘crash blossoms’ are, and where their grasp of English grammar went. Here are some other examples:

Squad Helps Dog Bite Victim

This militarization of the police really has gone too far.

Red Tape Holds Up New Bridge

Bridge appallingly fails to win structural design awards.

Infant Pulled from Wrecked Car Involved in Short Police Pursuit

An infant being chased by police? Don’t stop there. This goldmine of creative English grammar can even produce the image of an infant chasing away small-statured officers--no doubt from the wreckage of a crash blossom.

British left waffles on Falklands

Grab your syrup! First one to the Falklands gets dibs! Meanwhile, back in Britain, the political lefties continue to argue--about the Falklands, and probably about proper English grammar.


Hi, British? It’s the Falklands. You forgot something.

Landmine claims dog arms company

They can have our dog arms company when they pry it from our cold dead fingers. But why are we arming dogs again? Perhaps so the squad can help them bite victims.

Related Post: How to Translate Donut in 10 Awesomely Unique Languages


Assorted Oddities of the English Grammar Underbelly

We’ve seen garden path sentences, syntactical ambiguities, and some wonderful crash blossoms. But here are some oddball English grammar hijinks that don’t seem to fit into any definition. These sentences take us to the very fringes of language and thought, where only madness lies.

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

This sentence demonstrates the nine possible pronunciations of -ough in English grammar. Yes, nine! They’re all there: uff, oh, aw, ow, oo, uh, ew, off, and up. Who wrote this language, anyway?!

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

Every word has one letter more than the last. Count ‘em if you like! And while the sentence is a precocious mouthful, it does technically makes sense in English grammar.

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.

Oh, you zany -ing words! A gerund is a verb that functions as a noun. But not all -ing words are gerunds. They can be adjectives, present participles, or independent nouns as well. Spend some time on this English grammar headdesker and the meaning will come into focus:

This very annoying jerk, who considered long-winded remarks about the use of appropriate words to be a show of transcendent education, was displaying, despite ridicule, great brags that inflate logic, about the correction of incorrect writing, and touched upon the detection of false arguments during debates.

And it doesn’t even make mention of anomalies like morning or ceiling! How those fit into the wild world of English grammar will just have to remain a mystery.

You have just begun reading the sentence you have just finished reading.

Mind. Blown. Now that you’re watching the thoughts you are having about reading this, consider yourself #woke. English grammar is the new third eye opener.

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

Right? Right. Try pronouncing it this way:

Red rhymes with led, and reed rhymes with leed, but reed and led don’t rhyme, and neither to red and leed.

Are you up for chopping a tree down, or are you down to chop it up?

Have you ever tried explaining to a non-native English speaker the difference between being ‘down’ for something and ‘up’ for something? It seems like they should be opposites, but they mean almost the same thing.

For some reason there’s a more clear distinction between chopping something down (to fell a thing) versus chopping it up (to dice a thing into little pieces). Who knows why? English grammar is a runaway boat which no man dareth to helm.

Chopped Wood

Our confidence in English grammar, after reading this

A dangling preposition is something up with which I will not put.

This one comes from my high school AP English teacher. Hi, Mr. Flygare! I’m a writer now.

Colorless green ideas sleep furiously.

This is a nonsense sentence composed by Noam Chomsky in his 1957 book Syntactic Structures. It makes grammatical sense, but carries no meaning. But the real point, though, was that Chomsky chose a sequence of words that he presumed had never been uttered before in the context of English grammar.

This was to counterpoint the idea that language is the result of certain words statistically following on the heels of others. In other words, Chomsky was showing that true creativity and originality are indeed attributes of human language--that English grammar is not merely a mechanical or mathematical process.

And that’s why, after all this tongue twisting, we love our human translators. Machines just can’t do these kinds of English grammar backflips.

Enough of This Slap-Dash English Grammar! My Brain is Nigh Become Mush!

Hopefully you’ve enjoyed this trip down the English grammar rabbit hole. Now that your brain is a turgid puddle, please share this post with your linguaphile friends and colleagues so they can smart-laugh with you. And don’t forget to look out for Buffalo buffalo who buffalo Buffalo buffalo all the time. They can’t be trusted!

Brian Oaster

Brian Oaster is a Content Writer at Day Translations. He has worked all over the world as an arts educator, English teacher, basket exporter, bookstore owner, fortune teller, and as the first mate of a private sailing yacht! Educated in the visual arts and an avid reader of news and literature, his focus is on international arts and culture, world religions and global politics.

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