I tried two of our former Prime Ministers ... Kim Campbell and John Diefenbaker, and he nailed it!
Took more Q+A's before he came up with Lucy Maude Montgomery. Just tried Scott Thompson, first guess he went with Brent LeRoy, about six more questions and he got Scott. Almost stumped him with Buddy Cole .... he came up with seven possibilities, including Scott who plays him, then eventually got it
Curious for the ones who stumped him, were your people "very" obscure? And were you answering a lot of I don't knows or probably/nots? I wasn't sure how to answer some of the questions when it was a character role, so expect that caused the long-drawn-out session.
I guess this is programed like the computer that played Jeopardy on TV!!