If you want to annoy them, flood them with insipid questions and cookie cutter comments with the curiosity of a kindergardner. Either they're so warped and think you're stupid, or they'll get it and crack. It's like pulling teeth for both of you, but you get to be the dentist.
One method my brother still uses against me is to adamantly agree with me in the most sarcastic voice possible: "oh, your TOTALY right, that's EXACTLY the way it is... what? I'm agreeing with you, you're a GENIOUS..." A second method from Evelyn Waugh's Scoop is to say, "definately" when he says something you can agree with and "Up to a point" when you would otherwise disagree.
