“The Shakespeare of our time.”
Stephen Sondheim practically reinvented musicals with his flair for theatrical storytelling through his lyrics and music. A lesser known fact is that Sondheim also played a huge role in the puzzling world.

Before he was famous for musicals like West Side Story, Sweeney Todd, and Sundays in the Park with George, Sondheim was the first puzzle editor for New York Magazine in the 1960s. Sondheim’s obsession with puzzles and games lasted his whole life. He discovered escape rooms while in his 80s, and played many of them! Sondheim famously said “art, in itself, is an attempt to bring order out of chaos,” and the same could very much be said for puzzles.

Barry Joseph joins us on REPOD to talk about his new book, Matching Minds with Sondheim, which dives into Sondheim’s love of puzzles and games. The types of puzzles spanned everything from crosswords, to treasure hunts, jigsaw puzzles, and parlour games. Little known fact—Stephen Sondheim is credited with bringing British style cryptic crosswords to the USA! He also commissioned custom jigsaw puzzles as opening night gifts for the cast and crew of his Broadway shows.




As prolific as Sondheim was with his musicals, he was equally invested in his puzzles and games. Guest Barry Joseph digs deep into all the different ways Sondheim incorporated puzzles into his creative work and daily life. If you found this topic interesting, be sure to get his book, Matching Minds with Sondheim and check out his podcast of the same name. I’d recommend starting with the two podcast episodes that featured our very own David and Lisa Spira: Escape Room Episode (ft. Lisa & David), Jigsaw Puzzles Episode (ft. David).
Thank You to Our Sponsors
We are immensely grateful to our sponsors this season: REA Patreon Backers, PG’s Playhouse, Buzzshot, and COGS. We truly appreciate your support of our mission to promote and improve the immersive gaming community.

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By becoming a Patreon supporter, you’re not just backing a blog — you’re fueling a mission to make the escape room and immersive gaming community stronger, more thoughtful, and more connected. You can also access exclusive Patreon content such as the Bonus Aftershow, Spoilers Club, and get early access to escape room Tour tickets and REA articles.
Your Patreon support goes toward our mission: paying our contributors, funding our infrastructure, and supporting deep research and industry advocacy.

PG’s Playhouse Podcast
If you love wordplay, puzzles, and trivia, this is the podcast for you! PG’s Playhouse recreates a fun game night with friends, all in a short, 30-minute format. Of course, what’s game night without making new friends? We bring on different guests for the different episodes!
Each episode features a puzzle packed with wordplay and trivia, a short chat with the guest, and a segment exploring an interesting topic. I hope you’ll take a listen and play along with us at PG’s Playhouse.
Buzzshot
Buzzshot is Escape Room Software, Powering Business Growth, Player Marketing, and improving the Customer Experience. They offer an assortment of pre and post game features including robust waiver management, branded team photos, and streamlined review management for Yelp, TripAdvisor, Google Reviews, and Morty. Buzzshot now has integration with the other REPOD sponsors: Morty and COGS.
Special Offer for REPOD Listeners:
REPOD listeners get an extended 21-day free trial plus 20% off your first 3 months, with no set-up fees or hidden charges. Visit buzzshot.com/repod to learn more about this exclusive offer.
COGS
COGS by Clockwork Dog is an easy to use software/ hardware platform for running interactive events, including escape rooms, and other immersive experiences. They have plug & play hardware that seamlessly integrates with their software so you can create a show with lighting and sound cues without having to write a single line of code. Map all kinds of inputs to outputs by building up simple logic steps which determine what you want to happen and when.
Special Offer for REPOD Listeners:
REPOD listeners can get the COGS Starter Set for only $130 + free shipping to the USA. This bundle is usually valued at $257. You can learn more and purchase your Starter Set at cogs.show. Use code REPOD at checkout.
Topics Discussed in this Episode
- 00:00 Sponsor Break: Buzzshot, Escape Room Marketing Software
- 03:35 Sondheim’s Legacy in Musical Theater
- 07:34 Sondheim and the World of Puzzles
- 16:08 Cryptic Crosswords: Sondheim’s Influence
- 22:36 Sondheim’s Love for Jigsaw Puzzles
- 25:58 Sponsor Break: Room Escape Artist Patreon—Bonus Episodes, Spoilers Club & More
- 30:10 Sondheim’s Puzzle Design Philosophy
- 33:55 Dissecting Sondheim’s Approach to Lyrics and Games
- 34:57 Sponsor Break: PG’s Playhouse – Puzzles, Pals, and Trivia
- 36:39 Sondheim’s Treasure Hunts
- 39:19 The Influence of Sondheim on Escape Rooms
- 42:30 Sondheim’s Experience with Escape Rooms
- 49:52 Sponsor Break: Cogs By Clockwork Dog, Interactive Show Controls
- 50:51 Hostilities: Sondheim’s Cruel Parlor Game
- 54:39 Barry’s Journey in Education and Games
- 58:17 The Games for Change Organization
- 59:42 Where People Can Find Barry’s Book
- 01:01:21 What Comes Next?
- 01:03:08 Final Thoughts and Anecdotes
- 01:04:21 Credits
- 01:04:44 Paradiso Story
Leave a Voicemail
Got a question or thought for the podcast? You can submit a voice recording by calling the Room Escape Artist not-so-hotline that always goes straight to voicemail (551-227-7273).
Resources Mentioned in this Episode
- Matching Minds With Sondheim Website
- Matching Minds with Sondheim Podcast ft. Room Escape Artist
- Purchase Matching Minds with Sondheim on Amazon (affiliate link)
- Sondheim Books Mentioned:
- Robert L. McLaughlin’s Stephen Sondheim and the Reinvention of the American Musical
- James Lapine’s oral history, Putting It Together: How Stephen Sondheim and I Created “Sunday in the Park with George.”
- 1998 Meryle Secrest biography: Stephen Sondheim: A Life
- Stave Puzzles
- Paradiso Reviews
About Barry Joseph

Instagram: @MatchingMindswithSondheim
Barry Joseph is the Principal of Barry Joseph Consulting, a leader in innovating solutions for learning in a digital age, and the co-founder of the Games for Change Festival. As an early developer of after-school game design youth programming and an adjunct instructor at New York University, Barry has been a national leader in games-based learning and games for social impact, producing dozens of curriculums, games, and exhibits.
Collaborators and clients have included the American Museum of Natural History, Girl Scouts of the USA, the RAND Corporation, the MacArthur Foundation, and City College of New York. Barry has been featured by The New York Times, The Wall Street Journal, CNN, CBS Morning News, All Things Considered, and many more. He authored Seltzertopia and co-founded and directs the Brooklyn Seltzer Museum. Learn more at his website MatchingMindsWithSondheim.com.
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