Books
Matching Minds With Sondheim: The Puzzles and Games of the Broadway Master (2025)

By near-universal consensus, Stephen Sondheim was the greatest musical theater composer of his generation. Matching Minds with Sondheim is a journey into the rich but largely unmapped puzzle and game aspects 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.
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
Learn more at MatchingMindswithSondheim.com and on Instagram.
The New Yorker: “Clever and appropriately obsessive.”
Drama Book Shop: “So popular we can’t keep it on our shelves.”
The Times of London: “Read the book.”
Making Dinosaurs Dance: A Toolkit for Digital Design in Museums (2023)
“A wonderful guide to the kind of agile, experimental, responsive operational strategies needed in the museum of the future.” — Elizabeth Merritt, Founding Director, Center for the Future of Museums, American Alliance of Museums
Making Dinosaurs Dance takes the reader behind the scenes to learn how the American Museum of Natural History innovates visitor digital engagement, highlighting design techniques used both there and at museums around the world. Based on my six years at the landmark institution that inspired the Night at the Museum franchise, the book introduces The Six Tools of Digital Design – user research, rapid prototyping, public piloting, iterative design, youth collaboration, and teaming up – then applies them through case studies across a range of topics.
Read more here.
Friday is Tomorrow, or The Dayenu Year (2022)
Chronicles from the NYC Covid-19 Oral History, Narrative and Memory Archive
“Stories like Joseph’s suggest we are a lot better than we think we are.” —Micki McElya, author of The Politics of Mourning
“Compulsively readable” —James Loney, columnist
Friday is Tomorrow, or The Dayenu Year is a true story of learning to grieve and thrive during the first year of the COVID-19 Pandemic.
Within the first month of the lock-down, the author loses his father to the disease and then, soon after, his job. Through the support of his family, friends, and community, Friday is Tomorrow tells the uplifting story of how one man learns to maintain traditions in a time of uncertainty while reaching for his dreams.
At times moving, at times humorous, the ups and downs of this New Yorker were originally penned (quite literally, with a physical pen) for Columbia University’s NYC Covid-19 Oral History, Narrative and Memory Archive. Edited together for the first time, Friday is Tomorrow is more than just an opportunity to read one person’s struggle with the world wrought by the recent pandemic.
It is an invitation to take the time and space you need to consider and better understand your own story.
Learn how to get your own copy, download a free sample, and more at FridayisTomorrow.com.
Seltzertopia: The Extraordinary Story of an Ordinary Drink (2018)
“Of the thousands of books written about seltzer water, this is by far my favorite–especially the part that’s about me.” –Mel Brooks
Based on more than fourteen years of original research and interviews, the extraordinary story of this ordinary drink can finally be told.
Learn where to get your own copy, watch videos of presentations, follow the book tour and more at Seltzertopia.com.




