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James while John had had had had had had had had had had had a better effect on the teacher
No, that's not a typo. I randomly came across this article in Wikipedia. Apparently it is used by teachers to demonstrate punctuation and the ambiguity of the word "had". The sentence really does go as follows: James while John had had had had had had had had had had had a better effect on the teacher. To make sense of this, you can add the correct puctuation, below:
James, while John had had "had", had had "had had"; "had had" had had a better effect on the teacher.
Now it's all clear, huh?
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