Here are a few sentences that utilize the numerous standard definitions of the same English word. Each of the "multi" words are pronounced the same way.
The Club owner asks the cancan girl if she can can her attitude, and get her can off the can, before he has to can her.
And by the way, can the cancan girl can the cancan until the can can be fixed after the can from the peaches she'd put in a can can be retrieved from said can?
Here is Sushi's contribution:
As he'd fallen down a well and was set to die, and following their well set drill, as the sun set the press set upon the drill press operator to press him mercilessly for news about the tool and die set machining record hed set so well that day.
Note that these are all single, gramatically correct sentences. Furthermore, almost none of the "multi" words repeat the same meaning twice.
Do you know any similar sentences? Let us know!
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Sometimes even proper grammar won't cut it. This sentence, which is perfectly correct, was taught to Dennis by his old English teacher:
The teacher said that that that that that boy used was incorrect.
Doubt it? Try using "the" in two places instead:
The teacher said that the that that the boy used was incorrect.
Here's a fascinating page maintained by a High School teacher in Florida.
A Collection of Word Oddities and Trivia