Month: November 2025

It’s Saturday evening. A team of six puzzlers have spent the past five hours traveling across New York City for a hunt, and just decoded a sequence of responses from a custom Ouija board: the answers to the thirteen questions they had just asked spelled out GPS coordinates to a nearby office complex. Upon arriving at their destination, they rush past the Alamo Drafthouse to reach their next destination: a non-profit filled with vibrantly decorated pianos, arranged in rings of four. Multicolored stickers adorn several keys on each piano, practically begging to be played. And identifying the songs they’re about to perform is only the first step.

This experiential snapshot was from the charity puzzle event Midnight Madness. Famed composer and playwright Stephen Sondheim was not directly involved in the creation of this hunt, and none of his songs were featured in the puzzle that unfurled as teams tickled the ivory. And yet, as Barry Joseph argues in his new book Matching Minds with Sondheim, that event (and many more like it) might never have happened had it not been for Sondheim’s passion for puzzling.

Joseph makes an incredibly compelling case, tracing Sondheim’s influence through everything from puzzle hunts and cryptic crosswords to escape rooms and even board games. The book highlights how the puzzles and games that Sondheim created as intimate gifts for friends, family, and colleagues shaped the modern puzzling landscape.

In Good Company: Sondheim’s Surprising Puzzling Cameos

Much of the thrill of Matching Minds with Sondheim comes from learning how deeply embedded Sondheim was across early puzzling communities. Fans of Sondheim’s musicals might be surprised to learn that he moonlit as New York magazine’s first puzzle editor, starting with the magazine’s launch in 1968. During that tenure, he helped popularize the cryptic crossword format to American audiences, simplifying elements to be more approachable. And while Broadway fans may have been familiar with his longtime friendship with fellow composer Leonard Bernstein, the fact that he created a series of three narratively linked board games known as The Great Conductor Hunt to celebrate the man’s 50th birthday is less publicized.

Even Sondheim’s Broadway casts were enlisted into his puzzling fun. For decades up until his death in 2021, cast members would receive puzzles as elaborate opening night gifts…from custom engraved beans bearing a message of thanks for Into the Woods, to jigsaw puzzles with the recipient’s initials etched into the pattern.

Whether your puzzling passion leads you into the realm of video games (he was an avid fan of games like Myst), puzzle boxes (he had an extensive collection) or game shows (Sondheim spent years trying to hunt down a clip from his highly successful appearance on the game show Password), Matching Minds showcases Sondheim’s deep and abiding love for play.

Each of these forays into puzzles and games showcases a man infatuated with the many ways puzzles and games can spark creativity and inspire passion. In terms of puzzling tomes, I turn to AJ Jacobs’ The Puzzler as a tour of passionate puzzling communities. But Matching Minds with Sondheim may be my new reference book for showcasing why someone might fall in love with puzzles in the first place. And that celebration shines brightest (especially for ARGNet readers) in Barry Joseph’s section on treasure hunts, and The Murder Game.