- Do something remarkable.
- Oh, and do it before your 16th birthday.
It was just last April that 17-year-old Oliver Hill became the youngest constructor of a Sunday puzzle. Caleb Madison is still 15 and the old record is now toast. Yes, I know, you were amazing when you were that age too, but you didn’t have three published puzzles under your belt, did you?
Before I get to the puzzle itself, it seems like a good day to run an interview I did with the precocious Master Madison. Did I mention he's 15? That’s him on the right in the image. The gentleman on the left is Jemaine Clement of Flight of the Conchords. Caleb saw FotC in concert and describes himself as a HUGE fan.
Hi, Caleb. How did you get involved in crossword design?
I started in about 8th grade. Most of my interest stems from my grandmother, an avid Times solver, who brought a book of puzzles with her wherever she went. The whole family would get into the Sunday puzzles and it would become a group effort. Soon after, I began to do dailies on my own, working up from Monday to now about Thursday-Friday difficulty. I can do a Saturday with help from my dad, but my goal is to be able to finish at least half of a Saturday by the next American Crossword Puzzle Tournament.
How does it feel to be the youngest constructor Will Shortz has published?
It feels amazing. I hope I can keep making puzzles no matter how old I am. There is nothing like that first time, though!
What support have you got from friends and family?
I got so much support from everyone: my dad urged me at the ACPT to ask Will Shortz for the internship, my mom took my first puzzle and got it beautifully framed as a gift, my sister, whose name appears clued as the Irktusk river in my last puzzle, of course, my grandparents and other relatives, they have all helped.
What do your school friends think of your success?
They've also been greatly supportive. On the day my first puzzle was published, my friends Catherine and Sophie made me a homemade crossword congratulations card. Everyone was very excited.
What other puzzles do you solve? Or create?
Besides the NY Times puzzle which I do religiously on my train ride to school, I do the Sun crossword and occasionally the LA Times. I also love Will Shortz's NPR puzzle. I have a couple of puzzles coming out in the Sun soon, the first one I think is on 9/9.
What are your future goals?
I want to keep creating and solving crosswords as much as possible and compete (and have fun in) the ACPT. In other aspects of my life, I'll be happy just to make it through 10th grade and have some time for fun :-)
What makes a great crossword, for you personally?
For themed puzzles, I think it's all about the impact of the "aha" moment as Will Shortz calls it. It depends on the day. For a Wednesday or Thursday, the more original the better. Joe Krozel is an example of a constructor who, no matter what, is always innovative. For a Monday or Tuesday, I like good, not necessarily groundbreaking, but solid puzzles.
Which constructors do you particularly admire?
So many: Elizabeth Gorski, Henry Hook, Byron Walden, Joe Krozel. Also, Lynn Lempel and Andrea Carla Michaels for early week puzzles, as well as Bob Klahn, Mike Nothnagel, David J. Kahn, Peter Gordon and Rich Norris (both as editors and constructors). Also, all of the other teen constructors: Kyle Mahowald, Will Nediger, Patrick John Duggan, Oliver Hill etc. I'm sure I've missed some.
What has Will Shortz meant to you personally?
Wow, so much. Interning for him taught me a great deal about puzzles; it turned crosswords from a hobby into a passion for me. He revolutionized the puzzling world and he's a constant reminder of how, if you love doing something, you can make a career out of it. It was a lot of fun watching him in action.
Caleb always seems to get short shrift here because his puzzles come out when I’m doing an interview or some other special feature but this time it’s his own fault. The Sunday, August 17 answers are here. In his excitement to work on a big Sunday grid for the first time, he didn’t realize that some of his answers didn’t quite fit until it was too late, so they just Fade Out in the end. The theme is good, and no the puzzle doesn’t seem like it comes from a teenager. In fact, the thematic references are all from decades past.
Here’s a statistical oddity. “A Clockwork Orange” (16 letters) has appeared only once in a Will Shortz puzzle. A CLOCKWORK ORANG now has four occurrences.
And that reminds me of the very first puzzle Mr. Shortz edited for the TImes. It’s too far back to be on the nytimes.com web site but thanks to Barry Haldiman, I have a copy and you can try it here. I highly recommend it.