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Some people say that you can't use that phrase when the listener is in real bad situations, such as having their arm broken, car accidents or something like those, because the phrase could feel like "Hey that's nothing, just shrug it off and stop being childish".
But I've seen some scenes in many media where people use it even to the ones whose family member has passed away. How should I use "Cheer up" correctly?
'Cheer up' means become happier.
There is a difference between grammatically correctly and being socially aware.
Oh your brother has just died, cheer up!
is grammatically correct, but damn insensitive. It is now very rarely considered okay to say "cheer up", "smile it might never happen" etc unless you know the person and what has made them unhappy in the first place.
Here is a scene where it is okay, but it is not okay in virtually any other situation.
Wife: Why are you so sad?
Husband: I just spilt the whole bottle of milk
Wife: Cheer up! I will go to the shop and buy you another one, I was just going anyway.
"Cheer up" means to lighten one's mood.
It can be said to someone else as a request, or perhaps more accurately as words of encouragement, for example:
Why are you looking so sad? Cheer up! It can't be that bad!
It can also be used to describe the action of trying to help someone else to lighten their mood, for example:
I'm going over to John's house to see if I can cheer him up.
You are right that it can be said in a way that shows a lack of sympathy for the other person's condition. Context and tone of voice are what make the difference. Obviously, if someone grumpily says "cheer up, for goodness sake!" they are probably not particularly sympathetic towards your situation.
With your specific example of bereavement, I have to say that "cheer up" does seem inappropriate for this context. Most people understand that grieving is necessary, and telling a bereaved person to "cheer up" would be thought of as inconsiderate. However, many people do appreciate some levity during such a time, and it does not seem inappropriate to say that you would like to cheer someone else up, if they were suffering a loss.
Cheer up is used in this context to try and tell someone to not focus on something negative in their life. In your example, people trying to cheer up a friend who had someone pass away in their life, is them trying to get their friend to stop focusing on the negative emotions associated with death and to refocus on something else.
This is why just telling someone to "cheer up" when something is going wrong rarely works. It's like telling someone with a broken leg to simply not feel the pain instead of doing something to take the attention away from it.
