Five By Five, With Will Shortz The puzzlemaster leads an anagram showdown with Studio 360's Kurt Andersen and filmmaker David Wain
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Five By Five, With Will Shortz

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Five By Five, With Will Shortz

Five By Five, With Will Shortz

Five By Five, With Will Shortz

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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.