Matching Minds With Sondheim
By near-universal consensus, Stephen Sondheim was the greatest musical theater composer of his generation—celebrated, among other things, for the wit, sophistication, and intricacy of shows from West Side Story to Sunday in the Park with George. A less well-known avenue for his brilliant creativity was his lifelong fascination with designing and constructing intricate puzzles and games: from treasure hunts and crossword puzzles to parlor and board games.
Matching Minds with Sondheim is a journey into this rich but largely unmapped aspect of the composer’s creative life, illuminating how Sondheim’s playful designs delivered moments of clarity and connection for his friends and colleagues. For the first time, this book offers an enthralling tour of what Sondheim described as his “puzzler’s mind,” helping readers to better understand the man, his work, and—if they accept the challenge—themselves.
Gaming expert and theater fan Barry Joseph draws from over eighty years of Sondheim’s activities, collecting his extremely rare and never-publicly-seen puzzles and game designs, scores of original interviews with the celebrity friends who played them, deep dives into Sondheim-related archives from around the country, and analysis from both puzzle designers and theater professionals from around the world.
Matching Mindswill do more than describe Sondheim’s work: It will allow readers to match minds with the maestro by attempting to solve Sondheimian puzzles and bring Sondheimian games into their own homes.
Follow the latest on the book at MatchingMindswithSondheim.com and on Instagram. New web site and podcast series launching in June!
Well that was insane! An amazing crowd at @bwaycon with special guests @etaibenson , George Lee Andrews, and Marti Morris. Etai’s stories about receiving the last Sondheim opening night jigsaw gift is always so moving; I brought and he signed my Playbill from when I saw him in Company. (And the photo of Etai reading my book is him for the first time seeing his opening night letter from Sondheim reprinted in my book). George and Marti are Broadway legends and the most adorable couple! They shared about being in A Little Night Music and participating in Sondheim’s 1973 treasure hunt for the cast. The audience was game for my sing-a-long, solved Sondheim’s puzzles, and, oh, then I sold out all copies of my book. What a blast! If the audio turns out, I’ll share later in a podcast. @georgelandrews @sondheimletters
I had a wonderful time as a guest today on Broadway Nation, the podcast by David Armstrong that became a book (while my book became a podcast). I look forward to when it goes live (and I’ll repod it on my own when I can). David was a gracious, informed, and equally obsessive host, so of course it was a blast. Enjoy these behind the scene moments.
@broadwaypodcastnetwork @davidatbroadwaynation @alanseales
Discovered today by Michael Mitnick is a relatively unknown photograph by Hans Namuth of Sondheim with his puzzles and games (Note: The Game of the Jew on the ground).
A different Namuth photograph of Sondheim, aged 30, reclining in the study of his new Turtle Bay Home, reclining on his couch, paper in hand, Blackwing pencil between his teeth, is well known. Google “Hans Namuth Sondheim” and you’ll see it.
That one was taken Nov 1960 and published July 1961, in Horizon: “On Stage: Stephen Sondheim.” Namath’s book of portraits has this to say: Referring to an earlier photo, the text reads: “Sondheim…had recently secured his place in the history of American musical theater as the lyricist for West Side Story and Gypsy. For this Horizon commission, Namuth photographed Sondheim in Manhattan in his Turtle Bay townhouse. The elaborate house, with its enormous stained-glass window, was once owned by renowned editor Maxwell Perkins. As a setting, it underscores the life of luxury that has come to the young and talented Sondheim as the result of the success of these musicals.”
According to Namuth’s Appointment Diary, Sondheim met Namuth for the first time on the day of the shoot and never since.
That means we know the photo shown here was taken on the same date, with Sondheim lying on the other direction of the same couch. I guess the magazine was more interested in Sondheim composer/lyricist than Sondheim game player. Here Sondheim, cigarette in hand, seems trapped by an invading army of board games and puzzles!
So how can we see it now, if it was never printed in Horizon?
Sondheim must have received a copy (or more than one) from Namath, which he then gifted to Dominick Dunne. Dunne then included it in his 1999 book The Way We Lived Then, on page 8. Dunne writes in the caption “The inscription says ‘To Nick and Lennie. A casual pose. With love, Steve.’” and then recounts his memories of being in college with him at Williams.
If I am lucky I’ll be able to find an original and secure the rights to include in a future edition of Matching Minds. (Maybe? Pretty please?) @sondheimletters @sondheimphotos @michaelmitnick
Surprise! BroadwayCon is a last minute addition to my speaking schedule, and I couldn’t be more excited.
This Saturday, as part of BroadwayCon’s three-day packed agenda of presentations and workshops and sing-alongs, on Saturday afternoon I’ll be offering my “Sondheim… and the Game of Murder” presentation. And this time I am announcing my special guest in advance: Etai Benson!
Cut-stage left: “There’s no better way to represent his brilliance than through puzzles because his mind to me was a grand puzzle.” Back to center.
Etai Benson is an actor best known for his Broadway career, with credits including The Band’s Visit, Wicked—and the reason why he’s joining me on stage—Company.
But not just any Broadway-staged Company. This production—COVID-stalled in March 2020 then resumed in November 2021—became the final production in a string that began with 1993’s Putting It Together to receive as an opening night gift from Sondheim a deviously designed, customized, personalized jigsaw puzzle.
Cut-stage left: “I mean, if someone would have just given you a little puzzle with the logo, like, dayenu, that would have been enough. But the fact that he made sure that there was that personal touch and that personal detail of our initials, it felt like a conversation with him.” Back to center.
I can’t tell what I am more excited about—presenting at BroadwayCon or getting to meet in person for the first time the man behind the many quotes in this post cribbed from my book’s interviews with Etai!
Cut-stage left: “I look at that Company puzzle, and it’s the loss of innocence for me. I can sort of measure my life before Company and after Company. So, it comes with a lot of emotion.” Back to center.
So if you are planning to attend BroadwayCon this Saturday please let me know if we can look forward to seeing you. (A book signing will follow).
@etaibenson @bwaycon
What do these 3 things have in common: a temple men’s club, NYTime’s crossword commenters, and museum designers?
They were all talking about Matching Minds this week!
Tuesday I went to the men’s club at the Forest Hills Temple, where we played Sondheim parlor games and puzzles.
Wednesday’s New York Times’ crossword puzzle was Sondheim-themed. Here’s their description from Wordplay, their crossword column:
“This theme pays tribute to a certain BROADWAY MUSICAL (17A) called “Sunday in the Park with George,” composed by the [Pulitzer-winning composer and lyricist] STEPHEN SONDHEIM (60A). By connecting the circled letters, starting with the letter at square 39, we get a notable song lyric from the musical, LOOK I MADE A HAT. And wouldn’t you know it: Connect the dots of these letters, and you’ll see that you have, in fact, made a hat.”
In the comments of their Wordplay column, I shared the following:
“…Finishing the Hat... could have been called Finishing the Game. In 1965 his friend Phyllis Newman had a show flop out of town. He asked what he could do and she said make a game for me when I return. He designed The Murder Game in an overnight 11-hour creative fugue... In the early 80s… he wanted to write a song about that experience, about disconnecting from the world to pursue a creative pursuit, not to paint something new but to create a playful way for his friends to connect. So now, his song, about a game, has been honored in a crossword. Quite fitting.”
The 1st person who replied wrote “I was just reading your book when I turned to this puzzle! It’s fantastic and I think readers of this column would love it.” That was awesome.
On Thursday I joined NYC Content and this time the people playing Sondheim games and solving his puzzles were museum design professionals. We played but also dug deeper into practices behind Sondheim’s ludological creations and how they could be applied within museum experience design.
Then, afterwards, someone else replied to my NYTimes comment: “I was hoping you solved this puzzle!” she wrote. “Perfect timing for the local activity you ran Tuesday night.” She was a member of the synagogue! Small world…
@reformtemplefh
Walter Wick made a generous contributions to Matching Minds. Walter is an artist (best known for the two series of I Spy and Can You See What I See?). For me, Wick’s history was most relevant because of his time working at Games Magazine, which led him in 1982 to the home of Stephen Sondheim. Once there, he took photographs of both Sondheim and his remarkable games and puzzles collection (much of which was destroyed in his 1995 fire).
Walter provided me these photos, many of which went into the book and others shared in this post.
After reading my book, Walter generously emailed me some thoughtful feedback. With his permission, I’m sharing a few excerpts below:
“Thank you for sending me a copy of your terrific book, Matching Minds. I enjoyed it so much. It really brought me back to a time when I was in and out of the offices of Games magazine, and they in turn, at my studio on a regular basis, shooting covers (my first cover is on the top of the stack shown on p. 255) and feature puzzles... I was quite surprised (and delighted) to find myself a “cast member” of chapter 1. I loved the somewhat impish expression you selected of Sondheim at the piano, rescued as it were, from a handful of frames that would never otherwise have seen the light of day. You can say the entire book is a resurrection of the unseen side of Sondheim, with the crown jewel being the breathtaking discovery found in the Secrest tapes, which cleverly segues to the chapter on opening puzzle boxes. Another favorite moment was the City Center treasure hunt reenactment, with each participant struggling, then succeeding, only to be followed by each having epiphanies about similar mechanisms at work in Sondheim’s musicals. You reported how Sondheim tried to play such connections down – and I get it. He didn’t want it to become shorthand, a one-size-fits-all TV soundbite to explain the full scope of his artistic practice. But I bet he would have grinned (impishly) to have heard his friends make those connections. I couldn’t have been an easy book to write, but you knocked it out of the park. Congratulations!”
Thank you Walter!
@walterwickstudio @sondheimphotos
Name ten tracks by Sondheim that highlight his love of games and puzzles. That was the challenge posed to me by Donald Feltham, who invited me back to his streaming Broadway Radio Show. We discussed songs like “10 Years Old,” an unproduced gem from the 1960s, “When?” from the TV musical Evening Primrose, “Poems” from Pacific Overtures, and “No More” from “Into the Woods.” We explore Sondheim’s attempts to incorporate puzzle elements in his work, including an educational CD-ROM for Into the Woods, and highlights his personal life through the backdrop of his love for parlor games. The closing track, “Finishing the Hat” from Sunday in the Park with George, underscores the intersection of Sondheim’s musical genius and his passion for intricate puzzles. Come join our rollicking conversation.
Make sure to get the book everywhere books are found, or click the link in my bio.
#Sondheim #Theatre #Podcast @broadwaypodcastnetwork @colmmolloy_ @ndta_am @broadwayradioshow
SATURDAY, NOVEMBER 9
10 a.m. “Puzzles, Lyrics, and Other Word Games” Stephen Sondheim answers all of your questions about all of the above.
The year: 1991.
The place: Mohonk Mountain House, the more than 150-year-old resort in upstate New York.
The event: The Wonderful World of Words, founded nine year earlier by Gloria Rosenthal and her husband Larry.
In the fall of 2025, I was lucky to present at the Words Weekend, now one of Mohonk’s longest-running theme weekends (run for many years by Will Shortz, now by @GregPliska).
After my presentation about Sondheim, I was delighted and surprised to learn Sondheim himself had presented there “sometime in the past,” likely from the same stage!
Amy Rosenthal (Gloria’s daughter) and Nell Boucher (Mohonk Archives Manager) provided me both this photo of Sondheim (seated next to Gloria Rosenthal) and this printed late addition of Sondheim’s talk to the weekend’s always-packed program.
I was thrilled to see this photo because it is unique. Since research began on my book I have found photos of Sondheim designing treasure hunts, defeating escape rooms, and playing video games. But what I never found were photos of him within gaming and puzzling communities.
In 1968, he crashed a cryptic gathering in London, which led to his decade-long involvement with APEX, an invite-only crossword community; when Sunday went to London in 2005, a member of the Gruntlings (a monthly crosswords meet-up) invited him to join, and he did. Paul Henderson, a member told me:
“I wrote to Sondheim asking if he might want to attend Grunts. He rang me up at work - ‘Hi! It’s Steve Sondheim!’ - and I nearly dropped the phone. He agreed to come.”
Alas, no photos! So this one of Sondheim within the marvelous World of Words community is the first public photo we’ve seen of Sondheim moving beyond his private world of solo solving and parties with friends to bring his passion out into the wide world, among others who felt the same.
@mohonkmountainhouse @gregpliska @sondheimletters @sondheimphotos
When I read this, it made me cry.
I’ve had many feelings since my book came out last October, but this is the moment I’ve been waiting to feel - where Sondheim is discussed in public and my book is used to reference Sondheim’s passion for puzzles and games.
As if, “of course.”
As if, finally, Sondheim’s playful side can no longer be ignored, is no longer a surprised, is just assumed to be true.
The common understanding of who Sondheim was forever altered, at first citing my book as the source but then, eventually, my book drops away, becomes redundant.
All authors want the same thing: for their book to find their readers, to have good sales, etc. But specifically this is what I also wanted for my book, to change how people understand who Sondheim was and how his mind worked.
This piece, in the Times of London, is my first step towards redundancy. That’s what made me cry, as I was so moved. It is the first sign that my dream might be coming true.
“There was… a quirkiness to Sondheim’s psyche that his more solemn disciples overlook. Barry Joseph’s new book Matching Minds with Sondheim homes in on how a lifelong passion for puzzles and games fed into his stage work…”
This article, btw, is about a new podcast series, which will begin March 5th. It’s a collaboration between the composer Peter E Jones, Sondheim’s archivist and former partner, and the British author, performer and director Martin Milnes. And it looks like it will be amazing (and be source of more tears for many)! Check it out: @lovingyousondheimpodcast
@martinmilnes @MatchingMindsWithSondheim
Select blurbs:
“Matching Minds with Sondheim is literally a mind-boggling study, providing more than 400 pages of background and insight that sheds new light on an incredible creative mind. Joseph offers solid evidence about how Sondheim’s pursuit of puzzle solutions and elaborate game playing were part and parcel with his mastery of words. If you desire a deeper understanding of this modern genius, this is a book for you.”
—Rick Pender, author of The Stephen Sondheim Encyclopedia
“Matching Minds accomplishes a truly remarkable feat: reintroducing us to someone we thought we already knew. It’s not just a biography of Stephen Sondheim but a sourcebook and design guide to his creative work. An absolute must-read for any puzzle or game designer.”
—Eric Zimmerman, Arts Professor, New York University Game Center, and co-author of Rules of Play
“Reliving my extraordinary night participating in Stephen’s 1968 Halloween Treasure Hunt was like stepping back into the genius’s boundless imagination. This book is a treasure hunt in its own right, piecing together the magic and mystery that Sondheim conjured in every puzzle, every clue, and every note he composed. A fascinating read that guides you through the wonderland of one of the world’s most brilliant minds.”
—Grover Dale, original cast member of West Side Story, Tony- and Emmy-nominated Dancer, Choreographer, and Director
“Matching Minds reveals how before Stephen Sondheim was a musical theater god he was the puzzle editor at New York magazine, making ‘order out of chaos’ on a weekly basis. Discover how puzzles weren’t just a hobby for Steve, but a window into his brilliant mind, and his ever-illuminating music.”
—Melissa Errico, Tony-nominated Broadway actress/writer; recording artist of two Sondheim albums; star of Sunday in The Park With George at The Kennedy Center & more
“Riddle me this: Who loves Sondheim? Who wants to have incredible insight into how Sondheim’s love for puzzles shaped his brilliant writing? Who needs to read Matching Minds With Sondheim?
ANSWER: Everyone who loves musical theater!”
—Seth Rudetsky, musician, actor, writer and radio host
“Just as Sondheim treated his audiences as though they were at a level playing field, so too does Barry Joseph with this fascinating series of insights into Sondheim’s genius that even non-gamers will gobble up.”
—Julie Klausner, creator, Difficult People, and Sondheim enthusiast
“If you’re bedazzled by Stephen Sondheim and want to get inside his mind, you need this book. If you’re equally entranced by puzzles and games, you must read this book immediately and repeatedly. Matching Minds is a real accomplishment, and no one but Barry Joseph could have written it. His intelligence and commitment to this complex subject can be found on every page.”
—Daniel Okrent, author of the forthcoming Stephen Sondheim: Art Isn’t Easy
“Barry Joseph’s Matching Minds with Sondheim reveals an untold dimension of the Broadway legend’s life: his passion for puzzles and games. From designing murder mystery party games to crafting immersive and puzzling treasure hunts, Joseph paints a vivid picture of how Sondheim channeled his wit and precision into the art of making play.”
—Michael Mitnick, playwright, songwriter, and Sondheim aficionado
“Matching Minds shows how Sondheim was exactly the type of player that makes the escape room community so vibrant.”
—Lisa and David Spira, co-creators of RoomEscapeArtist.com
“Setting and solving puzzles lies at the heart of creativity, whether the output be lyrics, music, or crosswords. In Joseph’s Matching Minds with Sondheim we finally learn how this puzzling spirit pervades the works of a master of all three.”
—Paul Henderson, cryptic crossword setter and APEX custodian
“As someone who spends most of her time trying to discover what makes Sondheim great, the book gave me another lens through which to understand his genius. Now, whenever I approach a show, a song, or a set of lyrics, I ask myself: Is it a puzzle? Is it a game? Is it playful? And that’s been eye-opening and invigorating.”
—Gail Leondar-Wright, independent Sondheim scholar (TalkingSondheim.com)
“A treasure trove of insight into Sondheim’s deep engagement with games, the people with whom he played them, and what they reveal about his ‘puzzler’s mind.'”
—The Sondheim Hub

