A friend of mine wrote the other day the following:

We all know that that so isn’t how it works.

It amused me, but also seemed to be (as far as I can tell) grammatically fine. It led to the response:

I’m glad that that that that amused you.

Even better.

I came across this article the other day on Mental Floss. It has some further examples of grammatical weirdness:

• The horse raced past the barn fell.
• The complex houses married and single soldiers and their families.
• The rat the cat the dog chased killed ate the malt.

And of course my favorite:

Buffalo buffalo buffalo buffalo buffalo buffalo buffalo buffalo.

In case you need help with that one, “buffalo” can mean the animal, the city, and the action “to buffalo” (i.e. to bully or intimidate).

But, I believe I have one to top all of that, and it’s true, too. Here is a sentence with the word “and” in it five times in a row:

There’s too much space between north and and and and and son.

Got it? No?

This relates to my grandfather’s business in North Yorkshire. When the eldest son came of age, he needed to change the business sign from North to North & Son. When the sign maker came back, the words had been crushed together:

North&Son

Enraged, he returned to the sign maker the next morning with the words:

There’s too much [bloody] space between North and & and & and Son!

I never knew if they got it fixed.

Like this.