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Background

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.

Challenge

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.

Notes

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.

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closed as too broad by Glorfindel, APrough, Hugh Meyers, DqwertyC, Beastly Gerbil Feb 6 '18 at 17:57

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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    $\begingroup$ I actually found this: english.stackexchange.com/questions/46277/… , does this answer your question? $\endgroup$ – Gustavo Gabriel Feb 5 '18 at 18:00
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    $\begingroup$ ... but is this really a puzzle? $\endgroup$ – Rubio Feb 5 '18 at 23:25
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    $\begingroup$ This doesn't appear to have anything to do with Puzzling site scope: it is not connected to understanding, creating, analysing, or solving puzzles. It might be tangentially separately related to those topics, but that puzzles may feature bicycle pumps would not make bicycle pumps on topic to ask about either. Even in in the phrase given there are only three different usages, and "most" as a superlative isn't necessary to construct another such phrase. $\endgroup$ – doppelgreener Feb 6 '18 at 11:39
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    $\begingroup$ If this does remain on topic, can we please categorically exclude expletives? The F-word and others already virtually have the most diverse meanings (due to sort of having no one meaning at all), but I don't think we'd be pursuing making such a phrase out of expletives. $\endgroup$ – doppelgreener Feb 6 '18 at 11:43
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    $\begingroup$ @Randal'Thor I didn’t vote to close, but I don’t think this belongs here. It’s going to get bogged down in how to define parts of speech, something that was a challenge even on English.SE in the similar question linked earlier in the comments. The central element of picking the best answer is going to be in deciding which submission actually is comprised of a set of strict homonyms that cover the largest number of distinct parts of speech-including figuring out what parts of speech each usage actually is, and if they overlap. To me, that makes it a language question, not a puzzle. $\endgroup$ – Rubio Feb 6 '18 at 19:23
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How about..

Shit.

Noun, uncountable:

Look at this shit.

Noun, countable: *

Who gives a shit?

Intransitive verb:

I gotta shit.

Transitive verb:

Come on, don't shit me.

Proper article:

Shit just got real.

Pronoun:

Little shit took my sandwich.

Quantifier pronoun (slang, US):

The word "shit" has shit tons of meanings.

Conjunctive Adverb:

I come here most days; shit, maybe every day.

Adverb (slang, UK):

This engine runs a bit shit.

Adjective (slang, UK):

That's a shit song.

And of course Interjection:

Shit!

* I'm aware that nouns are generally either countable or uncountable, but it seems this one can be used either way. This gives us flexibility similar to what we get from "buffalo" being the plural of singular "buffalo."

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    $\begingroup$ You could say the same of a certain four-letter word beginning with F. In fact, in English class at school we saw a short film to that effect. It was very entertaining. $\endgroup$ – F1Krazy Feb 6 '18 at 11:32
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    $\begingroup$ @F1Krazy, now that you mention it, I'm sure there was a post like that on one of the English SE sites a few years back... $\endgroup$ – Guest Feb 6 '18 at 11:32
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    $\begingroup$ Yeah, the s-word's got f*** all on the f-word, except that the latter takes on the "ing" suffix in many of its roles. $\endgroup$ – Bass Feb 6 '18 at 12:01
  • $\begingroup$ Now I'm tempted to try f- without f-ing it up with suffixes. $\endgroup$ – Guest Feb 6 '18 at 16:48
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    $\begingroup$ @F1Krazy uncyclopedia.wikia.com/wiki/… $\endgroup$ – Quintec Feb 8 '18 at 19:11
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We can argue if this counts as English or not, but

Fit fit fits fit fit?

is a Doric phrase meaning "Which foot fits which shoe?"

It's not as long as the Buffalo one, but if we accept accents and dialects alongside dictionary English it opens up a lot more areas where we might find something longer than it.

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I found this Source which cointain multiple words that answers your question, but I thought of another word, with four uses:

The word Fine

It can be:

Adjective: "this was a fine piece of filmmaking"
Adverb: "And how's the job-hunting going? Oh, fine."
Noun: "a parking fine"
Verb: "he was fined $600 and sentenced to one day in jail"

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