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.

Into the Puzzling Woods: From The Murder Game to Last of Sheila

Stephen Sondheim was obsessed with parlor games, and created a whole series of games that he would challenge his friends and family to tackle. He became particularly enamored with murder mystery parties, and created his own version to fix what he saw as some of the flaws of the format: so, he created The Murder Game in 1965, which constructed a murder mystery game with a puzzling twist that meant you could only play it once.

To begin the evening, players are handed numbered envelopes with instructions to retrieve a clue, hidden somewhere within the house. If the murderer catches you while trying to retrieve the evidence, they can either destroy the evidence or take it as their own before the survivors reconvene to sort out who the real killer is, based on the evidence left behind. I won’t spoil the trick here, in part because Matching Minds with Sondheim includes a version of the Murder Game that you can try and solve along as you read. But it’s a delightfully clever mechanic that provides even the killer’s silenced victims a chance to figure out what secret their evidence pack contained.

Sondheim went on to create increasingly elaborate hunts for friends and family. the Halloween Treasure Hunt was his first foray into puzzle hunts in 1968, sending teams of puzzlers throughout Manhattan in limousines. Sondheim’s ambitions only grew, with later hunts. The events were often created as gifts to close friends and family, and might include taking over the Shubert theater for a puzzle hunt that could only be solved by the cast and crew of A Little Night Music, or asking players to exchange cross-continental faxes with Stephen Fry. For one of his rare public hunts, Sondheim even teamed up with Hollywood power couple Sarah Jessica Parker and Matthew Broderick to take over the American Museum of Natural History for a charity event priced at $1,500 a head.

Inspired by his experiences playing The Murder Game and some of Sondheim’s earlier puzzle hunts, director Herbie Ross turned many of the games and puzzles Sondheim used to torture his friends into the 1973 film The Last of Sheila. Sondheim himself collaborated on the movie’s screenplay, delighting in baking puzzles into everything from the film to its promotional materials. After viewing the film, puzzlers Donald Luskin and Patrick Carlyle were so inspired that they created their own puzzle hunt on the West Coast called The Game. This in turn inspired the movie Midnight Madness in 1980, which went on to inspire the puzzle hunt of the same name that started off this article. Sometimes, the nods get explicit. As Barry Joseph notes, homages to The Last of Sheila are so prevalent in the Benoit Blanc mystery Glass Onion that giving Sondheim his own cameo as one of Blanc’s colleagues in Among Us…which itself is an evolution of Sondheim’s Murder Game.

These explorations of creative provenance are some of the most deeply researched parts of Matching Minds with Sondheim, and why I feel comfortable going into so much detail about this particular subsection of the book’s subject matter. The book celebrates Sondheim’s story through the recollections of people who actually participated in his games and puzzles, through bite-sized puzzle snippets you can solve as you read, and through winding paths that show how Sondheim’s impact in the spaces he loved echoes to this day. One particularly heartwarming anecdote mentions how Sondheim’s love of escape rooms took him to the Dante-themed production Paradiso, only to learn that one of the puzzles he designed in 1968 was incorporated into the modern escape room as obscure homage. At another point, Barry Joseph even stages a Zoom playthrough of one of the better documented hunts, enlisting friends from various corners of Sondheim’s puzzling life as participants.

Sunday in the Park with Barry: The Author As Puzzle Master

In case you haven’t guessed yet, Matching Minds with Sondheim is more than just a book. Many of the pictures scattered throughout this article were taken at the Drama Book Shop’s pop-up exhibit dedicated to Sondheim’s penchant for puzzles, which ran through the month of October. Joseph also launched a podcast, featuring extended interviews with many of the experts consulted for the book. The episodes on escape rooms and The Last of Sheila are likely of particular interest to ARGNet readers. And that’s not even getting into the book’s hidden puzzles.

The first secret puzzle in the book is fairly easy to find: the book’s dedication is a series of enumerated spaces, left as a cryptographic exercise for the reader. Pairing that enumeration with something that appears later in the book makes it possible (although still difficult) to work out Barry’s intended message. The next puzzle takes a little more attention to discover, but starts getting a little more personal.

While paging through the book’s index, you might be surprised to find a few out of place references, including a mention of Sentient Machine Therapist Dr. Jeanine Salla. No mention of Dr Salla appears on the referenced page, she’s just…there. This might make a bit more sense with some additional context about Barry Joseph himself, as he didn’t arrive at the subject of this book by happenstance.

In addition to being one of the co-founders of Games for Change, Joseph was also one of the initial ARG players known as “Cloudmakers”, who participated in The Beast, which is often credited as the first alternate reality game. And a stray reference to Dr Jeanine Salla in the promotional materials for the film Artificial Intelligence served as primary trailhead for The Beast. If the text of the book is a tour through Sondheim’s love of puzzles and games, this embedded puzzle trail is a tour of Barry Joseph’s own passions for the space.

Anyone Can Puzzle: Sondheim’s Other Legacy

ARGNet has covered a number of celebrities and their passion for puzzling in the past, from Neil Patrick Harris and Alex Hirsch to Taylor Swift. And while they have all left their marks, it’s hard to overstate how much of an impact Stephen Sondheim has left on the puzzling world. So, to close out this coverage of Matching Minds with Sondheim, I thought it would be fitting to highlight some of the hunts and experiences that might not have existed without Sondheim.

ARGNet has already covered Great Gotham Challenge, but Sondheim-inspired treasure hunts aren’t limited to New York City. Earlier this year, Different Area Same Hunt returned with a half day puzzle hunt that played out simultaneously in 25 different cities, leading teams of 3-5 through a series of locations to pick up fiendishly clever puzzles wrapped in a light narrative. This year’s hunt led participants on a safari through an animal sanctuary. A personal puzzling highlight was this year’s “Duck Konundrum” puzzle, a following-directions style puzzle that our team members play a game of trivia with each person doing something completely different.

As the resident #CrowFacts expert on our team, I was charged with ignoring all the actual trivia questions and spouting out dubiously accurate facts. Did you know that according to science, at some point each of us will die? Duck Konundrum puzzles are an exercise in trusting the process: the tasks you’re charged with doing may seem like nonsense, but if you follow every instruction to the letter, things have a way of working out and delivering an answer.

In a 2011 WIRED interview, DASH creator Deb Goldstein notes that it was created as a slightly more accessible offshoot of Bay Area Night Game (which in turn was a more accessible version of The Game). DASH also provides a free print-and-play archive of past hunts, making it one of the more accessible hunts for those interested in hosting their own Zoom Party playthroughs.

Midnight Madness NYC leans in more towards Sondheim’s charitable hunts as inspiration, asking teams to donate a hefty sum to charity as the cost of entrance. This year I volunteered as part of Game Control, doling out hints to teams as they raced across New York City until 3AM. This year’s hunt was Houdini themed, and teams were handed “magic wands” that helped make the city come alive. A particularly cinematic sequence led teams throughout a series of street corners in Alphabet City, with magical encounters along the way. Eventually, teams learn that the locations they were visiting mapped to a secret card order often used by magicians. Proceeding to the next locations in sequence (while reordering a deck of cards provided earlier) led to a major reveal.

Even the MIT Mystery Hunt owes a debt of gratitude to Sondheim. While credit for the puzzle hunt’s origin is a bit more circuitous than the previously mentioned outdoor hunts, Matching Minds with Sondheim notes that Mark Halpin would frequently send Sondheim “cryptics that were created for MIT or for various puzzle events”, so Mystery Hunt constructors can now wonder if one of their own puzzles ever graced Sondheim’s desk.

What’s particularly heartening about Matching Minds with Sondheim is that it shows off how a creative legacy can be about deeply impacting a small circle of like-minded colleagues who share a passion for the art, as much as anything else. The Murder Game was a parlor game designed for a handful of people and yet it helped inspire an entire subculture.

A number of friends in the puzzle community have recently started celebrating birthdays by asking friends to create bespoke games and activities for the celebration. During these events I’ve taught a course on lockpicking despite not being able to pick locks. I’ve mailed 3D printed Moo Dengs to out-of-state friends so that they could surprise the birthday girl at conferences by dramatically handing over tiny pygmy hippos. And I recorded a video triggered by a NFC tagged necklace.

And as much as Matching Minds with Sondheim makes me contemplate how major projects like the Gravity Falls ARGs inspired an expansive fan project, it also brings to mind the impact of those more intimate creative explorations that are intended as a gift to a loved one, or celebration for a small group of friends.

For more on the Matching Minds with Sondheim book and podcast, visit MatchingMindsWithSondheim.com. It doesn’t just provide a rich and evocative history of a man who deeply loved puzzles…it celebrates how that love can take root in others, and blossom into something bigger. Reading the book even inspired me to overcome my long-standing aversion to cryptics. That’s right, I finally started teaching myself the format (with a little help from the Minute Cryptic daily puzzles).