<EM>Daily Show</EM>'s Jon Stewart is a fan of puzzlemaster Will Shortz (inset). Daily Show's Jon Stewart is a fan of puzzlemaster Will Shortz (inset).

What's an eight-letter word for a star-studded new documentary? Wordplay, going into wide release this Friday, offers a compelling look at Will Shortz, editor of the New York Times' venerable grid, and the annual American Crossword Puzzle Tournament. Along the way, such famous faces as former President Bill Clinton, Daily Show host Jon Stewart, filmmaker Ken Burns and New York Yankees ace Mike Mussina each detail their solving hobbies, and in turn give props to the Times' puzzlemaster. After seeing the doc, TVGuide.com took some questions to Shortz, confident that he could fill in the blanks.
 
TVGuide.com: My previous writing gig involved constructing the occasional crossword, so all I have to say is thank goodness for "individual retirement accounts"!
Will Shortz:
[Laughs] That's very good.

TVGuide.com: Whose idea was it to chronicle the Times crossword and the annual tournament up in Stamford, Connecticut?
Shortz: Patrick Creadon
, the director of the film, and Christine O'Malley, his wife, are crossword doers who actually just got into it about five years ago, but they really love the Times crossword and thought it would make an interesting subject for a documentary. Patrick left a message on my machine at the Times, asking if I would be willing to do this. Basically, I say yes to anything that I can fit into my schedule. I didn't dream that this thing would ever be so successful, but I said, "Sure! I'll do whatever you need."

TVGuide.com: Were you impressed and/or delighted with the amount of famous faces they got to pimp for you in the film? I mean, you've got Clinton, Jon Stewart....
Shortz:
I knew about all of them being big crossword fans, and it was very cool that they were able to get such important people in the film. Especially Bill Clinton talking about how solving a crossword is like tackling any challenge or issue in the White House  I thought that was great. And Amy [Ray] of the Indigo Girls talking about how solving a crossword is like writing a song. And Jon Stewart... well, he is just hilarious.

TVGuide.com: How does it feel to see Jon Stewart so familiarly taunting you on the big screen, "Bring it on, Will Shortz!"
Shortz:
That was so over the top, it's very cool and flattering.... It's nice.

TVGuide.com: Having grown up in Stamford, I was proud to see the Marriott representing.
Shortz:
I started the tournament there in 1978, back when it was a brand-new hotel.

TVGuide.com: I remember that the new Marriott was a big deal. The revolving restaurant had the town transfixed!
Shortz:
I worked summers in Stamford for a crossword-magazine company there. That was starting in 1974, and in my first year, that area was literally a slum. And look at it now!

TVGuide.com: When did you first realize such heavy-hitters were in the "Will Shortz Fan Club"?
Shortz:
In 1992, when Clinton was first running for president, I was the editor of Games magazine, and the publisher was a friend of Clinton's, so I got to interview him about his interest in puzzles. Clinton solved a crossword that we created for him, while we watched, in six minutes and 54 seconds  and he was on the phone, talking, half the time. You knew right then that this is somebody who's a solver.

TVGuide.com: Ever do a clue alluding to his Oval Office indiscretions? Or does that go against the Times crossword style rule about never referencing bodily fluids?
Shortz:
[Laughs] That has nothing to do with the rule. It just seems tawdry, so I wouldn't do that. But [attorney general Janet] Reno and [transportation secretary Federico] Pena, both cabinet members of his, appear in crosswords a lot. In January 1997, on the Sunday before Clinton was inaugurated for his second term, I ran a crossword in the Times that was all about him and his cabinet. He wrote afterward [saying] how much he enjoyed that. He solved the crossword while he should have been polishing his inaugural address.

TVGuide.com: What's the story about you helping Jon Stewart propose to his wife?
Shortz:
He called me around 1995, '96, and left a message saying, "Hi, this is Jon from The Daily Show...." Now I don't have cable TV and he didn't say his last name, so for all I know he was the gaffer or something for a TV show I didn't know. But he said he and his girlfriend were both huge New York Times crossword fans, and he wanted to propose to her through a crossword. He had tried to make the puzzle himself and completely failed, so he asked if I would help him. I wasn't able to do it myself, but I got a friend of mine to do it. The puzzle is now framed on his wall. When I was on his show a couple of years ago he joked that if his girlfriend had solved the crossword incorrectly and filled in the wrong name, would she have to marry a different guy?

TVGuide.com: That's funny  she could have promised herself to Rod Stewart. What word or words to this day vex you?
Shortz:
Hmm, what vexes me.... This answer doesn't trick me, but it tricks other people: randr. The first time I ran this answer, the clue was "Leave time?" I got letters and calls from people who said they couldn't find "randr" in their dictionary. Well, it's "R and R," as in relaxation. Every time I run that answer, always with a different clue, it tricks people.

TVGuide.com: When you use a relatively new celebrity as an answer, do you ever think, "This is going to make that person's day"?
Shortz:
Yes, that does cross my mind. There's a band leader whose widow once wrote me to say, "I've been solving the Times crossword for years, and it tickled me so much to see my Artie mentioned." It was really sweet.

TVGuide.com: Wordplay shows that a wide cross-section of people solve these puzzles, not all history and English teachers, as some might assume.
Shortz:
That's right. It's everyone from teenagers to as old as people get, evenly divided between men and women, and from all walks of life. Another preconception is that crossworders are all complete geeks, and what you see in the tournament is there are some geeky people....

TVGuide.com: Yeah, you'd better say some.
Shortz:
[Laughs] Any time you get an intellectual pursuit like this, you'll get some geeky people, but to be really good at solving crosswords you've got to know a little of everything, and it helps to have a flexible mind and a sense of humor. The best solvers are well-rounded, interesting people.

TVGuide.com: In closing, if I may get cerebral and heady here for a second... would you say the message of this film is "Sudoku is for sissies"?
Shortz:
No, I'm a huge Sudoku fan....

TVGuide.com: C'mon, it's all process of elimination!
Shortz:
Oh, there's more to it than process of elimination. Those are the very easy sudoku puzzles. Once you move onto the harder ones, they require higher levels of logic. I will not run down sudoku  I love it. I just like crosswords more.