Five By Five, With Will Shortz

Will Shortz joined Ask Me Another at Central Park's SummerStage.
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With New York Times crossword puzzle editor Will Shortz as our V.I.P. Puzzle Guru, we knew he'd come up with a doozy of a final round. In this game, recorded at Central Park's SummerStage, contestants are given two five-letter words, and asked to anagram one word to get a synonym of the second. And when the final two standing turn out to be Studio 360 host Kurt Andersen and Wet Hot American Summer filmmaker David Wain, the competition gets even more heated.

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