99 is More Than 100

When 99 is considered higher than 100?




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---------
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Replace the question mark with the correct number.

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There are people and strange monkeys on this island, and you can not tell who is who (Edit: until you understand what they said - see below). They speak either only the truth or only lies.
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Crossword

The day before the 1996 U.S. presidential election, the NYT Crossword contained the clue “Lead story in tomorrow’s newspaper,” the puzzle was built so that both electoral outcomes were correct answers, requiring 7 other clues to have dual responses.