Five By Five, With Will Shortz

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.

  • Studio 360's Kurt Andersen (left), filmmaker David Wain and civilian contestant Brian Gillis are the last three standing in this Ask Me One More final round. Who will be victorious?
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    Studio 360's Kurt Andersen (left), filmmaker David Wain and civilian contestant Brian Gillis are the last three standing in this Ask Me One More final round. Who will be victorious?
    Steve McFarland/NPR
  • Puzzlemaster Will Shortz may look like a nice guy, but he's crafted an anagram game so tricky, it could have only sprung from the mind of an evil supergenius.
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    Puzzlemaster Will Shortz may look like a nice guy, but he's crafted an anagram game so tricky, it could have only sprung from the mind of an evil supergenius.
    Steve McFarland/NPR
  • David Wain: Victory dance!
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    David Wain: Victory dance!
    Steve McFarland/NPR
  • But Wain has danced too soon. The next question is tough-- he must anagram one of these words to get a synonym of the other: CRUEL and MONEY. Defeat is cruel, indeed.
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    But Wain has danced too soon. The next question is tough— he must anagram one of these words to get a synonym of the other: CRUEL and MONEY. Defeat is cruel, indeed.
    Steve McFarland/NPR
  • When it's all said and done, Kurt Andersen wins!
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    When it's all said and done, Kurt Andersen wins!
    Steve McFarland/NPR

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