1

I watched a lot of American movies & it seems that most people would say "Why wouldn't you tell me that?"

Not many would say "Why didn't you tell me that?"

I think "would" here is future of "will" which means "willing to do something".

So, "Why wouldn't you tell me that?" would mean "why weren't you willing to tell me that?"

That is my thought but I may be wrong.

So, Why do people prefer to say "Why wouldn't you tell me that?" rather than "Why didn't you tell me that?"

2

Both questions are possible. "Why wouldn't you tell me that?", as you say, is asking for the reason for the other person's unwillingness to tell about a possibly hypothetical situation, while "Why didn't you tell me that?" merely asks for the reason for the failure to tell of an actual situation.

"Why wouldn't you tell me that my dog was dead?" - "Because I wouldn't like to upset you".

"Why didn't you tell me that my dog was dead?" - "I didn't know/I forgot".

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