Lots of research shows that doing mental exercises can ward off dementia and the effects of aging, but can it actually make you better at your job? While it’s hard to imagine the late musical theater virtuoso Stephen Sondheim needing any kind of extra creative stimuli, he in fact had a well-known love of stimulating puzzles and games.
And he didn’t just play them. The Tony-winning composer behind Broadway hits such as Sweeney Todd, Company, and a heartwarming ditty about presidential assassins also cultivated a side hustle as a designer of cryptic crossword puzzles and a frequent host of game nights and scavenger hunts.
Barry Joseph, a game researcher and designer and an adjunct professor at New York University, happened to notice a few years ago that no one had documented Sondheim’s niche passion in a comprehensive way. So he decided to do it himself.
His new book, Matching Minds With Sondheim (Bloomsbury, October 2025), draws from eight decades of Sondheim’s brain-teasing ventures. It includes a mix of rare and rarely seen game designs, archival research, and interviews with Sondheim contemporaries who played along.
Fast Company recently caught up with Joseph to discuss the book, what inspired it, and what he hopes readers will gain from trying to match minds with a musical legend. The interview has been edited for length and clarity.
You have a background as a game designer and game researcher. How did you get interested in writing about Stephen Sondheim?
Sondheim passed away in November of 2021. That means March, 22, 2022, was his first birthday after he passed away. And my birthday is two days later. For a present, my wife got me three Sondheim-related books . . . recognizing that I and many other Sondheim fans were still in mourning for having lost our musical hero.
One was an academic book that was a review of all Sondheim shows, but from the perspective of postmodernism. That book left me thinking how interesting it was to look at Sondheim through one lens. What other lenses might there be?
Then I read Stephen Sondheim’s biography from the late ’90s by Meryle Secrest, which barely talked about him having anything to do with puzzles and games. It’s mentioned here and there, but in the index in the back of the book, there’s nothing for games and nothing for puzzles—which tells you a lot about how seriously the topic was addressed.
And the third book was James Lapine’s Putting It Together—the oral history of Sunday in the Park With George. Lapine had met Stephen Sondheim right after Sondheim had his critical disaster Merrily We Roll Along. For those who don’t know, it was a show that lasted under two weeks and was completely decimated by the critics, putting Sondheim in a very unpleasant state of mind—so much so that when he met Mr. Lapine, he was talking about leaving the world of musical theater.
Lapine asked him what he was going to do next, and he said, “Maybe I’ll go into video game design.” That’s not what happened! They ended up working together to do Sunday in the Park With George. Sondheim kept doing musical theater. The rest is history, and they never mentioned it again in the book.
Me, as a young person who grew up in the late ’70s, early ’80s, playing my Intellivision, my Atari, my Apple II Plus computer, I read that and wondered about Stephen Sondheim designing video games instead . . .
I remember Intellivision being the middle stepchild of video game consoles. Not too many people had Intellivision.
I was one of those people. I always liked things being outside the box. . . . In any case, I read that, and that blew my mind. I thought, “What is Sondheim doing talking about games?” And I said, “Is there something here? Is there a topic here? What is the lens on Stephen Sondheim from a game perspective?”
Ludology is the study of games. And so I thought, “Can one look at Stephen Sondheim from a ludological lens?” And at the time, I didn’t know if there’d be much of anything. But after just a few weeks of some quick Google searches, what I found was that there were a lot of fascinating, enticing tidbits.
He was the founding puzzle editor of New York magazine in 1968. He created a cryptic crossword puzzle once a week. His only Hollywood-produced movie, The Last of Sheila, a murder mystery, involves all sorts of devious puzzles and games.
And I kept coming across these other mentions of people talking about going to his house for game nights. And there was an interview in Games magazine in 1983. There’s a bunch of his little tidbits here and there. And then the rest of it I found irresistible.
So you find all these breadcrumbs, publicly known facts here and there, and realize there’s no larger body of work that has compiled all this?
I learned enough to know that there was something there, and that it wasn’t waiting for someone just to write about. Because if it was, it would’ve been written.
Did you find a moment or many moments where his love of creating these puzzles informed his creative work in a really specific way?
The last chapter in the book is an analysis of all of his shows, looking at it from a playful language. Where are puzzles and games in the shows? Where are they in the structure of the shows, and where do they show up in the process of creating the shows?
And once you start taking this lens at his theatrical work, you see it everywhere. The end of Sunday in the Park With George is a moment where this painting that we’ve been watching constructed on the stage suddenly comes into focus. And it’s one that we know the audience has some prior knowledge of—they expect to see a certain something. Suddenly, it all happens in that moment when all the pieces all click together.
It’s those moments that Sondheim often talked about, where you’re forming order out of chaos. And that’s essentially a jigsaw puzzle being constructed.
And I’m now thinking about Merrily We Roll Along, which you mentioned earlier. It’s told backwards. That feels like it’s its own puzzle.
Think about it from the audience’s perspective, right? When you are watching something in which the effect happens before the cause, you have to hold it in your mind. And when you’re looking, it’s like a Where’s Waldo? What’s going to be the thing that caused that thing to happen? And then when you see it, it connects together. Sondheim didn’t write the book of Merrily, but I always wondered if that somehow influenced it.
And so we see it throughout the shows, in the structures of the shows, in the way that games and puzzles are used, and sometimes in the process of how they developed.
What if a reader wants to pick up your book—who is not necessarily super into puzzles or a hardcore puzzle doer? You have the puzzles in the book. Would the casual puzzle person find these kinds of puzzles challenging?
Let me answer your question in a roundabout way. . . . When I talk about all of his games and puzzles, I talk about three particular values. The first is the principle of generosity. The second is the principle of playfulness. And the third is the principle of mentorship.
Generosity means that I am here to help you have an engaging time. I’m here to make you feel good about yourself—not just feel good about how smart I am. And so it means creating opportunities to help people along the way. Helping along the way connects with the mentorship, which is building the scaffolding to help people solve the puzzles. And playfulness is just making it all fun.
You mentioned that your wife bought you three Sondheim books, so you must have been a fan before you started writing this. When did you discover your love of Broadway?
I’m laughing because I am in my room . . . and in my closet is a collection of Playbills that go back to the mid-1980s. I can’t even count how many are here. I grew up on Long Island. My mom loved musical theater, and it was a thing we often did as a family.
I learned very early on that I loved what it meant to be in an audience for a musical. I loved the magic that was created on the stage. And more importantly, I loved the emotions that it brought out in me.