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.
ART CHUNG: So when we asked Will back on the show to be our puzzle guru, he said he'd only do it if he could write the ASK ME ONE MORE final round game.
OPHIRA EISENBERG, HOST:
And he wrote one of the most challenging ones, because what did he write about? Anagrams.
CHUNG: That's right. Anagrams, if you don't know, are when you take one word and change all the letters to make another word. Like nudity and untidy.
EISENBERG: My brain does not think this way. I can't do it.
CHUNG: A lot of people's brains don't. But some people can really move the letters around in their head and form these new works. And the real tricky thing about this game is that we don't give them pen and papger. They're doing it all onstage in their heads in realtime.
EISENBERG: And that's why we call it diabolical, or my name isn't Heripe Begonious.
WILL SHORTZ: This final round is called "Five by Five." I'm going to give you two five letter words. Your challenge is to rearrange the letters of the first word to get a synonym of the other. For example, if I gave you strut S-T-R-U-T- and faith, you would say trust, which is an anagram of strut and is a synonym of faith. Now we're going to play this spelling bee style. So one wrong answer and you're out.
You'll have only a few seconds to give us an answer. Last person standing is our grand winner. Remember, rearrange the letters of the first word to get a synonym of the second one. Here we go. Kurt, you're up. Binge B-I-N-G-E to mean start.
KURT ANDERSON: Begin.
SHORTZ: Begin is correct. Sam. Fiber F-I-B-E-R to mean short. F-I-B-E-R to mean short. OK, time's up. Thank you, Sam. Cassidy, do you know fiber to mean short?
CASSIDY BROWN: No.
SHORTZ: OK. Sorry, Cassidy. Oh, David is in the hot spot. Fiber that means short.
DAVID WAIN: Brief.
SHORTZ: Brief is it. Yes.
SHORTZ: We're down to three contestants. Brian. Trams T-R-A-M-S to mean sting.
BRIAN GILLIS: Smarts?
SHORTZ: Smart is it, yes. Kurt. Lamed L-A-M-E-D to mean award.
SHORTZ: Medal is it. And David, uboat U-B-O-A-T to mean circa.
WAIN: About. About.
SHORTZ: About is it. Yes. OK.
SHORTZ: Well, you guys are so good we're going to make things a little more challenging. Now I'm not going to tell you which word is the anagram and which is the synonym. That's for you to figure out.
(SOUNDBITE OF AUDIENCE REACTION)
SHORTZ: Brian, this is your first one of these. Scope S-C-O-P-E and anger A-N-G-E-R. Scope and anger.
GILLIS: Gear? G--oh, sorry.
SHORTZ: Scope and anger. No, I don't hear the answer. OK. Kurt. Scope and anger.
SHORTZ: Range is it. OK. So we're down to two contestants. David, your clues are cruel C-R-U-E-L and money M-O-N-E-Y.
WAIN: OK. Ready? C-R-U...
SHORTZ: I think his time is up.
SHORTZ: Yeah. Kurt, do you know cruel and money?
SHORTZ: Lucre. Our champion.
EISENBERG: Well done. Kurt Andersen, you are our ASK ME ANOTHER big winner. Now, that was the final round. Will Shortz, everybody.
EISENBERG: Well, we've run out of Really Hard games. No, that's not true but that's all the time we have for our Really Hard Edition. I hope you enjoyed your workout. You can join us for a game any time, any place by subscribing to our podcast on iTunes. Or you can find us on Facebook or Twitter. Transcript provided by NPR, Copyright NPR.