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In Friends season 2, episode 1, at 18:35, Ross makes a joke about Monica's new haircut. He says "I think it's a ten". Chandler then does some jokes as well, such as "You could be caught between the Moon and NY city" and "I know it's crazy but it's true".

You can check the jokes here, at 2:55.

I don't get the double meaning. Can anyone explain the jokes?

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    A joke fails if you have to go on StackExchange to get it, and this joke failed bad...
    – Nelson
    Oct 26, 2016 at 9:48
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    This is clearly the result of a generation gap. People who were born during the late 1990's won't catch the majority of these pop culture jokes because they didn't live during the time. I've had something similar happen with How I Met Your Mother when my 13 year old nephew started watching season 1. You will get people who were born too late who watch the show and don't catch all the jokes because pop culture would have changed between then and now.
    – user42543
    Oct 26, 2016 at 11:05

2 Answers 2

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They're both references to Dudley Moore, which Monica was unfortunate enough to have his haircut. 10 is a famous film he starred in, while "When you get caught between the moon and New York City" is from the theme song of Arthur, another famous film Moore starred in.

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Just to clarify a little, Monica was supposed to get a haircut resembling Demi Moore's, but Phoebe mistakenly thought she said Dudley Moore. So she got a pretty bad haircut, and Chandler piled on the jokes referred to in Walt's answer.

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