I recently stumbled across the following grammatically correct sentence:
Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.
This sentence relies on the fact that the word buffalo could be multiple things, and that each of these is used as a different part of speech, namely:
- A city in New York (used as a noun adjunct).
- The American Bison (used as a noun).
- A verb meaning to intimidate of confuse.
The sentence roughly translates to: "Bison from Buffalo, which other bison from Buffalo intimidate, intimidate bison from Buffalo."
There's also a Wikipedia article for this sentence, which explains things more in depth than I do here. On a side note, it has my new favorite title for a Wikipedia article.
With that background, the goal of this question is to create a sentence made up of the most different homonyms of the same word. This is not a challenge to find the longest sentence consisting of one word. The "buffalo" sentence above has eight words, but only uses three definitions. And, as Deusovi pointed out on this somewhat similar question, a sentence using just the word buffalo could be made arbitrarily large.
I know this changes the scope of the original question, but hopefully previous answers can still be used to help form new answers.
While the buffalo sentence is nice in that all words used in it are spelled the same way, I will allow a mix of singular and plural variations of the word. I would also like a link or formal definition for each different use of the word, to ensure that each use is in fact an actual, even if narrow, use.