IIRC, Stewart interviewed him several months ago and tried to ask some hard questions, but Obama had direct answers and challenges for everything. By the end, Stewart couldn't even maintain good eye contact. That said, I suppose the President of the United States is probably one of the most challenging people in the world to interview. I can imagine his status being overpowering even to a seasoned interviewer. In all honesty, I can't even remember Dubya getting "schooled" in any interviews.
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Watch and you'll see... someday I'll be... part of your world!