As a rule, I hate ambiguity. I find it to be the representation of a flaw in the author's knowledge of his or her subject. Ambiguous language leads to confusion in audience members, and even when used purposefully like in a comedy of errors, it simply comes off as cheap and hackneyed.
Many rules, though, do get broken (especially when talking about what you can and can't do in writing). I have written recently about how annoying it is that the word "last" has two very common and very different meanings, which can make for very ambiguous and confusing sentences. However, it can also be used creatively and artistically.
In the Ben Folds song Annie Waits, part of the chorus goes, "Annie Waits for the last time / Just the same as the last time." This is a song about a woman who is consistently stood up by men, loses faith in it all, but keeps on going for the same kind of man, and thus getting the same results. I find those lyrics to be particularly poignant; they reinforce that the same thing keeps happening by using the same word, as well as what that word means. It is extremely creative and I applaud it.
Of course, if everybody used that turn of phrase, it would lose its efficacy, but since Ben Folds did it first (or at least most profoundly to me), it is amazing to me. It is proof positive that just because ambiguity (or ambiguous words) is bad in general does not mean that they cannot be used creatively.
Part of good writing is being able to find those loopholes, those creative ways to break the rules and be lauded for it.
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