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What does the expression "to make a tired point" mean? For example in this sentence:

To make a tired point, which one of us is truly crazy?

(It is from an episode of The Simpsons. Read the script.)

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When it is used as a statement, it means the point is already known but again raised. And due to this, it'll be a boring point.

The word in concern is the adjective tired.

tired: (Especially of a statement or idea) boring or uninteresting because overfamiliar

So, here, who is 'truly crazy' is a tired point because they already know that! It's just that the familiar question is raised again.

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A tired point is one that has been repeatedly raised.

The act of addressing the same point over and over again is sometimes called beating a dead horse; the actual point that is being raised over and over again is the "tired point."

Bill: I think we should buy new printers for the office.
Ted: Bill, you're beating a dead horse. We already told you: there's not enough money in the budget.

Bill: I think we should buy new printers for the office.
Ted: Bill, that's a tired point. We already told you: there's not enough money in the budget.

It's an understandable phrase, but I don't think it's all that commonly used.

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