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Matching Minds with Sondheim: The Puzzles and Games of the Broadway Legend
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 theatre 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 Minds will 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.
Reactions from early readers:
"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
“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
“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
“Anyone who loves the musicals of Stephen Sondheim is likely to know that the legendary composer and lyricist was also passionate about games and puzzles. Barry Joseph, himself a game designer, has taken that cue and assembled a whole new perspective shedding light on a facet of Sondheim’s creativity that’s not been explored previously in depth. His exploration is rooted in interviews with more than 60 puzzle and game designers, as well as Sondheim’s friends, colleagues and — especially — playmates. 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
“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 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 DOT com
“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
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 theatre 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 Minds will 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.
Reactions from early readers:
"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
“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
“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
“Anyone who loves the musicals of Stephen Sondheim is likely to know that the legendary composer and lyricist was also passionate about games and puzzles. Barry Joseph, himself a game designer, has taken that cue and assembled a whole new perspective shedding light on a facet of Sondheim’s creativity that’s not been explored previously in depth. His exploration is rooted in interviews with more than 60 puzzle and game designers, as well as Sondheim’s friends, colleagues and — especially — playmates. 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
“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 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 DOT com
“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
350 pages, Hardcover
First published October 2, 2025
About the author
Barry Joseph
4 books2 followersBarry Joseph is the Principal of Barry Joseph Consulting, a leader in innovating solutions for learning in a digital age. He is also the co-founder of the Games for Change Festival, the more than 20-year-old, multi-day event in New York City. As an early developer of after-school game design youth programming and now adjunct at New York University, Barry has been a national leader in both games-based learning and games for social impact, producing dozens of curriculums and games. Work and clients include the American Museum of Natural History, Girl Scouts of the USA, the RAND Corporation, the MacArthur Foundation, and the International Criminal Court. Barry has been featured by the New York Times, The Wall Street Journal, CNN, CBS Morning News, All Things Considered, and many more.
Ratings & Reviews
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Displaying 1 - 12 of 12 reviews
September 3, 2025
let's match minds with papa
Want to Read
October 27, 2025Best part of working at a library is pestering my coworkers into ordering every Sondheim book I can.
September 30, 2025
As someone who pestered Sondheim by means of written letter in 2018 for the instructions to the Murder Game after hearing about its existence thanks to a tweet from Mara Wilson in cab back on New Years Eve, I am so glad to finally have the detailed instructions.
The rest of the book is great too. I can't say I understand cryptic crosswords anymore having read it, but it's fun to read about something that was clearly a passion of his.
The rest of the book is great too. I can't say I understand cryptic crosswords anymore having read it, but it's fun to read about something that was clearly a passion of his.
November 13, 2025
I think this book may be the most personally affirming thing I have ever read.
I’ve spent plenty of time reflecting on the spiritual nexus of puzzles, games, and theater writing, and this book was everything I could ever hoped for, and so much more. It showed the brain and heart of one my heroes was way more like mine than I ever could have imagined. The breadth and depth of scope are so unbelievably satisfying. It boggles my mind (as I know it did yours) that such a significant piece of Sondheim’s being went so unexplored until now. Barry has done an incredible service for multiple communities, and as someone living at the nexus of many of them, I’ve never felt so connected.
If you love Sondheim, puzzles, games, or like me, all of the above, you’ll never find a more fulfilling and validating piece of writing.
I’ve spent plenty of time reflecting on the spiritual nexus of puzzles, games, and theater writing, and this book was everything I could ever hoped for, and so much more. It showed the brain and heart of one my heroes was way more like mine than I ever could have imagined. The breadth and depth of scope are so unbelievably satisfying. It boggles my mind (as I know it did yours) that such a significant piece of Sondheim’s being went so unexplored until now. Barry has done an incredible service for multiple communities, and as someone living at the nexus of many of them, I’ve never felt so connected.
If you love Sondheim, puzzles, games, or like me, all of the above, you’ll never find a more fulfilling and validating piece of writing.
March 17, 2026
A very fascinating and unusual biography. It did make me feel kind of stupid, though. Genuinely cannot believe anyone is smart enough to find those cryptic crosswords fun.
January 12, 2026
Sondheim the game & puzzles nerd - I love you
January 26, 2026
As someone whose interest in Stephen Sondheim doesn't extend much further than his play-fair mystery film "The Last of Sheila," I found this to be a slog. Barry Joseph is an enormous fan of Sondheim and demonstrates it with 300+ pages of hagiography. It's not enough to tell us that Sondheim liked cryptic crossword puzzles and wrote them himself--we're told about the history of cryptics, and the man who created them, and the man he inspired, who in turn inspired Sondheim, who in turn inspired another writer, and another... You don't just learn that Sondheim liked jigsaw puzzles, you get to read an interview with a man who was gifted a puzzle Sondheim designed once and who waxes effusively about how Sondheim was brilliant and smart and generous and brilliant and on and on and on.
Most frustratingly, for a book titled "Matching Minds with Sondheim" Joseph has a tendency to half-describe a puzzle Sondheim created and then provide the answer. You think that with all his research Joseph would have learned that most puzzle fans enjoy having the chance to solve a puzzle themselves, but I guess he missed that because he was interviewing a guy who works in an escape room Sondheim visited once.
Ugh. Recommended only for a Sondheim superfan.
Most frustratingly, for a book titled "Matching Minds with Sondheim" Joseph has a tendency to half-describe a puzzle Sondheim created and then provide the answer. You think that with all his research Joseph would have learned that most puzzle fans enjoy having the chance to solve a puzzle themselves, but I guess he missed that because he was interviewing a guy who works in an escape room Sondheim visited once.
Ugh. Recommended only for a Sondheim superfan.
February 28, 2026
Unlike his musical life (the "Hat Box" lyrics volumes total nearly 900 pages), Stephen Sondheim's life of puzzles and games had barely been explored. Barry Joseph's detailed and very well researched "Matching Minds with Sondheim" corrects that.
Joseph tracks Sondheim's 'gaming' life from a child solving anagrams to an old, quite famous man tackling escape rooms. With a level of detail which may be too much for some readers (not me), we learn of the treasure hunts, the murder game (and the only movie he wrote), the cryptic crosswords, the puzzles gifted to casts and crews on opening night, and the collection of antique board games and puzzle boxes.
In a way that can't be unlearned once read, Joseph even points out the puzzle or game in many of Sondheim's shows (e.g. "Into the Woods" is a classic quest computer game staged with music.)
Matching Minds also includes an extended section on how to craft games, throw a Sondheim game night, and solve some cryptic crosswords created for him (the ones he authored are out of print). Off to tackle one...and watch "The Last of Shiela".
Joseph tracks Sondheim's 'gaming' life from a child solving anagrams to an old, quite famous man tackling escape rooms. With a level of detail which may be too much for some readers (not me), we learn of the treasure hunts, the murder game (and the only movie he wrote), the cryptic crosswords, the puzzles gifted to casts and crews on opening night, and the collection of antique board games and puzzle boxes.
In a way that can't be unlearned once read, Joseph even points out the puzzle or game in many of Sondheim's shows (e.g. "Into the Woods" is a classic quest computer game staged with music.)
Matching Minds also includes an extended section on how to craft games, throw a Sondheim game night, and solve some cryptic crosswords created for him (the ones he authored are out of print). Off to tackle one...and watch "The Last of Shiela".
October 22, 2025
Matching Minds with Sondheim unveils an extraordinary and lesser-known dimension of Stephen Sondheim’s genius: his lifelong passion for puzzles and games. Barry Joseph meticulously explores how Sondheim’s creativity extended far beyond musical theatre into intricate treasure hunts, parlor games, and cryptic puzzles, offering readers a unique lens into the mind of a master composer and lyricist.
Through over 400 pages of research, rare archival materials, and interviews with Sondheim’s friends, collaborators, and fellow puzzle enthusiasts, Joseph illuminates the playful rigor behind Sondheim’s artistry. Readers are invited not just to observe but to engage with Sondheimian puzzles themselves, bridging intellectual play with creative mastery. This book is both an insightful biography and an interactive journey, perfect for fans of musicals, puzzle aficionados, and anyone intrigued by the confluence of art and intellect.
Through over 400 pages of research, rare archival materials, and interviews with Sondheim’s friends, collaborators, and fellow puzzle enthusiasts, Joseph illuminates the playful rigor behind Sondheim’s artistry. Readers are invited not just to observe but to engage with Sondheimian puzzles themselves, bridging intellectual play with creative mastery. This book is both an insightful biography and an interactive journey, perfect for fans of musicals, puzzle aficionados, and anyone intrigued by the confluence of art and intellect.
February 18, 2026
Generally loved the idea of this book and the stories that were told but didn’t 100% like the way it was written
March 15, 2026
An impressive amount of research in desperate need of a good editor.
May 14, 2026
I took my son to a talk and book signing by this author at the Museum of the City of New York; the talk sparked his interest but he seemed more exalted by getting the autographed copy.
A partial, sideways biography of Stephen Sondheim, through the lens of SS's lifelong hobby and obsession with puzzles, games, and real-life treasure hunts, predating the "escape room" concept, and connecting with his prodigious creative process. Kind of a niche interest and a nerdy love letter for gameplay and puzzle-solving.
A partial, sideways biography of Stephen Sondheim, through the lens of SS's lifelong hobby and obsession with puzzles, games, and real-life treasure hunts, predating the "escape room" concept, and connecting with his prodigious creative process. Kind of a niche interest and a nerdy love letter for gameplay and puzzle-solving.
Displaying 1 - 12 of 12 reviews