The strangest \"be more specific\" I ever saw on Jeopardy was a presidents category where a player responded with \"Who is Kennedy?\" Yes, there is a whole family of political folks named Kennedy, but if \'president\' is assumed in the category, I don\'t see the need for prompting.
I agree with Chuck that \'Wayans\' by itself should not have been enough.
I had a taping last night where I wanted \'Conestoga wagon\' and I prompted a kid who said \'covered wagon\'. He didn\'t get it, and later I felt bad because I don\'t think the question was specific enough as written. (It wasn\'t one of mine.)