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It's a line in the movie 'Shawshank redemption' when Brooks was saying about how hard to ask for funds in the jail is. But I haven't been able to translate this sentence for 3 hours. What's the actual meaning of this sentence? And if you explain these expressions(?) 'not one of them born whose as***le' and 'pucker up tighter than a snare drum' back to back, I'll be really happy. Thank you!!

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Alright. I'll go over each part, because there are multiple parts to this.

Not one of them born whose as***le wouldn’t pucker up tighter than a snare drum when you ask them for funds

First part:

Not one of them born

Since every person has been born at some point, this is just an expression meaning "all of them".

whose as***le wouldn’t pucker up

When the muscle around an orifice like the mouth or anus flexes / tightens, the skin of that orifice is forced to fold over. This is called "puckering". When a person makes their mouth very small to kiss another person, the skin of the lips is said to "pucker". When you say someone's anal sphincter has tightened, the implication is that the person is more tense, more stressed.

So this part of the expression is essentially saying "[the person] becomes tense because they are in an uncomfortable situation".

tighter than a snare drum

A snare drum is a type of drum where the surface of the drum is extremely taut. This just modifies the statement above from "uncomfortable" to "very uncomfortable".

when you ask them for funds

Hopefully obvious what this part means.

So the full expression means "All of them become very uncomfortable when you ask them for money". The implication is that they are uncomfortable because they don't like giving money, so either they will almost certainly say "no" (which is inherently confrontational, and people don't like confrontation), or they will say "yes" (which is unlikely, but would still mean they would be uncomfortable, because- again- they don't like giving money).

ADDENDUM: I'm assuming the above explanation is fine under the guidelines, since none of the above is gratuitous or lewd, we all have bodies, and to take issue with simply mentioning a body part by name in a dry, clinical fashion would be, for want of a better word, insane.

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    There is also the detail that an "anal retentive" person (look it up) tends to be obsessive, often in a very negative sense. And they tend to be stingy.
    – Hot Licks
    Commented Jul 12, 2018 at 23:52
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The meaning of the phrase is "Nobody likes to be asked for money."

I'm not going to provide a full answer that analyzes all parts of the phrase literally because it's an unfortunately rude expression. (And doing it the justice it deserves would likely violate the guidelines here . . .)

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