That was an interesting list in terms of all the meta analysis that went into it. But of all the items in the list, I think this calendar one would fare the worst against a Watson style AI, who would have a ranking system for recognizing topics and culture. The well known calendar rhyme would be a partial match, plus half the words in the rhyme are about calendars. The other topics would be poor matches for food, family, etc, only hitting once each.
What is the following rhyme about?
Thirty days has September,
April, June and no wonder,
All the rest have peanut butter,
Except my grandmother who has a little red tricycle.
A. Family relationships B. Calendar C. Food D. Exercise
source: http://www.britell.com/misc/turing.html
Not sure how long it'd stay viable though.