Contextualization

First let me define what is meant by contextualization.  According to Dictionary.com it is "to put (a linguistic element, an action, etc.) in a context, especially one that is characteristic or appropriate, as for purposes of study."
I have always disliked answers to questions that are yes and no but I think we will use a similar point here.
Contextualization is necessary.  Cultures do not understand the meanings of words the same as other cultures and to explain things you do have to put it in the context of the culture.

However, having said that it seems taht we cannot make the culture "king" in this.  We need to remember that the message is what is important.  We contextualize so that the message will be understood.  We don't contextualize to be "hip", "with it" but rather to make the message clear.  Someone said that we should teach with the Bible in one hand and the newspaper in the other.  Just remember that the newspaper does not interpret the Bible but the Bible will interpret the events recorded in the news.