“Police police police police police police police.”
Oh, homonyms and homophones. They let us construct statements such as the above (which, while a ridiculous thing to say, is a perfectly valid English sentence that could be rephrased as “Cops that are regulated by other officers regulate cops that are also regulated by other officers.”). If you want some extra-specific vocabulary, the noun ‘police’ and the verb ‘police’ are polysemes.
Maybe it’s just me, but I find something inherently humorous about legitimately using the same word (and to a lesser extent, letter) too many times in a row. You can almost feel the language glaring hatefully at you, like a cop (that may or may not be regulated by other cops) watching a criminal get away on a technicality.
One popular example used to demonstrate the importance of punctuation goes something like “John while I had had had had had had had had had had had proper grammatical structure.” When we add some orthographic organization, this string of madness actually makes sense – “John, while I had had ‘had’, had had ‘had had’; ‘had had’ had had proper grammatical structure.”
Perhaps the craziest exercise in homophony, however, is the Chinese ‘poem’/riddle by linguist Yuen Ren Chao entitled 施氏食獅史 (usually called “Lion-Eating Poet in the Stone Den” in English).
In its written form, it’s understandable enough (if you know Chinese, anyway):
It translates to something like:
In a stone den was a poet called Shi, who was a lion addict, and had resolved to eat ten lions.
He often went to the market to look for lions.
At ten o’clock, ten lions had just arrived at the market.
At that time, Shi had just arrived at the market.
He saw those ten lions, and using his trusty arrows, caused the ten lions to die.
He brought the corpses of the ten lions to the stone den.
The stone den was damp. He asked his servants to wipe it.
After the stone den was wiped, he tried to eat those ten lions.
When he ate, he realized that these ten lions were in fact ten stone lion corpses.
Try to explain this matter.
But, when read aloud in (or transliterated from) Mandarin, it becomes practically incomprehensible:
Shíshì shīshì Shī Shì, shì shī, shì shí shí shī.
Shì shíshí shì shì shì shī.
Shí shí, shì shí shī shì shì.
Shì shí, shì Shī Shì shì shì.
Shì shì shì shí shī, shì shǐ shì, shǐ shì shí shī shìshì.
Shì shí shì shí shī shī, shì shíshì.
Shíshì shī, Shì shǐ shì shì shíshì.
Shíshì shì, Shì shǐ shì shí shì shí shī.
Shí shí, shǐ shí shì shí shī shī, shí shí shí shī shī.
Shì shì shì shì.
It’s not perfectly homophonic because of tonal distinctions, but still. (>^-‘)> There’s a bit more variation when spoken in the other dialects that use the Chinese ideography (like Cantonese or Taiwanese), but either way, it’s really only followable in writing.
Languages are generally engineered to be as clear as possible, and where they fall short of that goal is something a writer should keep in mind – plus, abusing those problem areas can produce some entertaining results!