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David Kwong The Enigmatist

David Kwong’s new show The Enigmatist cross pollinates two of his pet passions: puzzles and magic.

Courtesy of Justin Barbin/Chicago Shakespeare Theater

More fun than Wordle: A new Chicago show draws from magic, puzzles and escape rooms

David Kwong’s The Engimatist, at Chicago Shakespeare Theater all month, is the performance for our puzzle-forward era.

Editor’s note: Hidden in this article is a code redeemable for 15% off tickets to Tuesday through Thursday performances of The Enigmatist between June 11 and 27. Search boldly for it and tell us at if you solve it.

The Enigmatist, a one-person show at Chicago Shakespeare Theater, does not fit neatly into any box, ironically enough for a show featuring crosswords. Writer and performer David Kwong, possibly the only person who could perform it, cross pollinates two of his pet passions to produce the show: puzzles and magic.

The hybridized result, which has run in New York, D.C., and Kwong’s hometown of Los Angeles, defines its own genre, somewhere at the intersection of magic, storytelling, and escape rooms.

Kwong is both an accomplished magician and a seasoned puzzle constructor. As a crossword constructor, he’s published 23 puzzles to date in The New York Times, “hitting for the cycle” along the way — that is, publishing at least one on each day of the week. As a magician, he has consulted on the illusions performed in the film Now You See Me and produced the TV show Deception. When he was conceiving The Enigmatist, marrying these two divergent but harmonious interests in a single something was its own puzzle.

In the show, he guides the audience through a series of puzzles that they solve together, live, standing up to indicate that they’re ready to share answers when they’ve got them. Between the puzzles, he weaves in a narrative about the founders of modern cryptography at Riverbank Laboratories in Geneva, Ill., with some planned misdirection and illusion along the way.

“There’s a box on stage, and I tell the whole audience that you’re going to unlock the box,” Kwong says, “as I tell you this wonderful story and I do magic tricks for you.”

The Enigmatist David Kwong

In The Enigmatist, Kwong guides the audience through a series of puzzles that they solve together.

Courtesy of Justin Barbin/Chicago Shakespeare Theater

It’s a clever next step for our current moment in puzzling. Quick, not too hard, and communal — that’s how we do our puzzles now. Wordle, for example, takes only a few minutes (or sometimes seconds), almost always ends with success, and took off because of social-media sharing. Crosswords have democratized, no longer favoring high culture and often running in miniature sizes. Cooperative, not competitive, dominates.

In the show, Kwong presents challenges to the audience and asks them to stand when they have the answer. He calls on someone — not necessarily the expert solver in the audience who pops up first. “The most exciting thing for me is when the 13-year-old kid cracks the final puzzle before all the adults, comes up on stage, and opens that box,” he says.

The show even invites the theatergoers to witness the creation of a crossword puzzle. “I think I’m the only performer of puzzles that I know of,” he says.How difficult should a stage show with puzzles be? If the audience must unlock the box, they have to be capable of solving the puzzles required to unlock the box. This differs from when a play, such as a murder mystery, presents a puzzling scenario that unravels during the show. If members of the audience solve it before the characters onstage do, it’s a disappointment. The best standard stage mysteries feel just barely unsolvable. Solvable = too easy.

Puzzlemakers, on the other hand, want their puzzles to be solved. They develop the skill of attuning themselves to the full spectrum of difficulty. Easy puzzles, like Mondays in The New York Times, have an audience in the puzzle world, as do Saturdays, the hardest. The Enigmatist calibrates its puzzles so that the audience will succeed. “That governs the entire show,” Kwong says. “Nothing is meant to be too hard.”

A good puzzle brings joy to the solver, without foregrounding the effort of the puzzle’s construction. Constructors imagine themselves in the place of the solver, and work in reverse to engineer their experience.

Solvers think: ‘I don’t want to have to remember that Esso still sells gas in Canada, or that an ell is a wing of a building known almost exclusively in crosswords. No — you tee it up, I hit it off. Oh, and throw a little rock-'n'-roll in there to spice it up.’

The closest analogue for this unique show might be the escape room, where a group of solvers is presented with a series of puzzles whose answers often generate codes or combinations to unlock boxes or doors that lead to the next puzzle, all within a set time limit. Some escape rooms employ actors who have particular duties in presenting puzzles but serve as supporting cast, a vessel for clues or a help line to appeal to for hints when stumped. In The Enigmatist, however, Kwong serves more as the master of ceremonies.

“I think the DNA for the puzzle portion of the show comes out of the parlor games that are played at the National Puzzlers’ League and other puzzle meetups around the country, where someone has devised a game or a puzzle and they offer it to the people in the room to figure out,” Kwong says.

He also traces the DNA to a formative experience, when his mother took him to see a lecture by Will Shortz, the Times crossword editor since 1993. Shortz did some games with the audience, along the lines of his NPR Puzzlemaster segments, where people solve snack-size puzzles — making the audience feel smart, Kwong says.

David Kwong The Enigmatist

Kwong lets the audience in on some magicians’ secrets in The Enigmatist.

Courtesy of Jeff Lorch/Chicago Shakespeare Theater

The idea of flattering the audience’s intelligence opposes the typical stance of magic shows. In many, the illusionist sets themselves apart from the audience as cleverer than them or somehow more than human. That is, the puzzle master wants you to feel smart, but many magicians want you to feel dumb. “A lot of the great magicians,” Kwong says, “they mesmerized you with their supposed supernatural abilities, and they’re penetrating your mind, and giving you a feeling of unease, and it works for them. And the daredevil magicians, and the escape artists, and the endurance artists — I think when you watch them, you sort of half-hope they’ll fall into the alligator pit.”

In the show, Kwong claims no magical abilities and lets the audience in on some magicians’ secrets. An audience member once told him he doesn’t do magic to people, he does magic with people. “By revealing the underlying principles of the tricks, I am acknowledging that you are smart enough to understand how these things work,” he says. In this source of tension, he’s resolved it unequivocally in favor of making people feel smart.

Really, this show, inviting all this verbiage to describe it, expresses the essence of David Kwong, making it unreplicable by just about anyone else on Earth. “It’s all the things that I love,” he says, “and that’s why it’s so fun. Because it’s almost like I’m teaching a class on how fun magic and puzzles can be.”

Intellectual play, with the audience in the sandbox. “Nerdfest,” Kwong lovingly calls it.

If you go: Chicago Shakespeare Theater presents The Enigmatist through June 30. Tickets from $59. Hidden in this article is a code redeemable for 15% off tickets to Tuesday through Thursday performances of The Enigmatist between June 11 and 27. Enter it in Chicago Shakespeare Theater’s online ticket portal to apply the discount.

Graham Meyer is a Chicago-based arts journalist.

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