As 60 Minutes first reported earlier this year, Shortz is the editor of The New York Times crossword puzzle, which is syndicated in newspapers all over the United States.
For nearly a decade, Shortz has used his position to revolutionize the genre, turning what used to be a straightforward educational exercise in synonyms into a mindbending entertainment. Correspondent Steve Kroft offers some clues on the Puzzle Master.
Shortz, 50, isn't a New Yorker, but a transplanted Midwesterner from Indiana. He created his first crossword at the age of 6 and sold his first at 14.
He's got the world's biggest library – over 20,000 books – containing, or about, puzzles. Ever heard of enigmatology? It's the study of puzzles and Shortz majored in it, receiving a B.A. from Indiana University.
"It sounds like a made-up word, but it's a real word," says Shortz. "It goes back to the 18th century. Originally, it meant the study of riddles and enigmas."
At his parents' insistence, he went on to earn a law degree from the University of Virginia. But he never bothered to take the bar exam, choosing instead to make a living in the puzzle trade. Eventually, he landed the editorship of Games magazine and later, the best job in all of enigmatology, The New York Times.
As the editor of The Times crossword, he likes to use words and phrases from popular culture and brand names. But his trademark is cleverness, originality and humor, using common words in an uncommon way.
"I use every misleading opportunity I can," says Shortz, whose daily puzzle appears in about 150 papers around the country.
The Times' online edition charges $19.95 a year just for the crosswords and generates enough revenue to pay Shortz's salary and his contributors several times over. Then, there's newspaper syndication and crossword books.
He does most of his work out of his suburban 1920s Tudor-style house in Pleasantville, N.Y., surrounded by an archive of puzzle memorabilia, including the world's first crossword puzzle that appeared in a 1913 Sunday supplement of the old New York World newspaper.
As crossword editor, Shortz rarely constructs the puzzle, but edits all the entries that do run, which he buys from a stable of freelance contributors. He gets 60 to 70 submissions every week, and he rewrites about half of the clues himself.
Submitting crossword puzzles to Shortz can make for an interesting hobby but not a well-paying career, unless you have a lot of extra time and puzzles on hand.
"If you're making your living from creating crosswords, you're either brilliantly fast, or you're living in poverty," he says.
He works about six weeks ahead and always sends a puzzle out to a group of friends, his personal testers, before firing it off to The Times.
When Shortz isn't coming up with diabolical plans to stump American crossword puzzle-solvers he spends his time with National Public Radio. For the past 15 years, he has hosted one of the most popular features on the radio show, no doubt making some of his Sunday morning listeners late for church.
He's also the founder, organizer and host of the annual American Crossword Puzzle Tournament, which earlier this year lured 400 fanatics from 36 states, Canada and Europe to Stamford, Conn., for three days of competition.
For those of you who take these puzzles personally, so does Shortz.
"Sometimes when I am taking the train, I will sit near somebody who is solving the New York Times crossword, just to keep an eye on them, see how they're doing," says Shortz. "My name is on the puzzle every day, and so, the solver is matching wits with me."
And if you are a good solver of crosswords, you just might meet Shortz some day. "If they do well, I introduce myself. If they don't do well, then I keep it my little secret," he says.
"Unlike a usual battle, where both sides want to win, this is a battle where I want you to win. I want you to fill in that last letter and feel the satisfaction of completing the challenge."
If you don't do crossword puzzles, but think you might like to try, one piece of advice: Don't start on the weekend. Shortz's puzzles begin pretty easy on Monday, a puzzle designed for novices. They get progressively harder each day. Sunday is the longest, but Saturday is the toughest.