Matching Minds with Sondheim: The Podcast

#28-Sondheim and Puzzle Boxes, with David Staller

Tue, 14 Apr 2026 07:00:00 -0000

Our latest episode focuses on Stephen Sondheim’s fascination with puzzle boxes, featuring guest David Staller, founding artistic director of the Gingold Theatrical Group. Staller describes his Shaw-inspired connection to Sondheim through Hermione Gingold, their friendship and correspondence, and Sondheim’s attraction to puzzles as finite, controllable structures that offered relief from the chaos of human relationships and creative pressures. The episode includes rare audio from Sondheim’s Games Magazine interview about collecting and admiring puzzle boxes, plus excerpts from Barry’s interview with puzzle-box designer Kagen Sound (on learning Sondheim was a client and seeing his boxes in the film Six by Sondheim). Staller recounts gifting Sondheim puzzle boxes (including Japanese artisan-made boxes), treasure-hunt parties and movie-themed murder mysteries, a final unopened birthday box returned after Sondheim’s death, and finding a hidden note during the 2024 Doyle auction. He also describes Sondheim’s love for, and association with the boy-star of, the comic strip Calvin and Hobbes.

00:00 Everything Is A Puzzle

01:44 Meet Guest David Staller

02:55 Shaw Connection To Sondheim

05:11 Why Games Felt Safe

07:54 Discovering Puzzle Boxes

08:46 What Puzzle Boxes Are

10:37 Sondheim On Puzzle Boxes

12:47 Voice Memories And Boxes

16:59 Japanese Artisan And Last Box

19:40 Opening The Box Onstage

21:53 What Was Inside The Box

23:25 Treasure Hunts And Movie Trivia

26:04 Thin Man Roleplaying Games

26:44 Movie Roleplay Mystery

28:34 Home Treasure Hunt

30:30 Sondheim Grammar Patrol

32:16 Puzzle Boxes Meaning

33:49 Kagen Sound Spotlight

36:04 Boxes On The Piano

38:04 Auction Hidden Note

39:42 Objects And Legacy

42:22 Calvin And Hobbes

47:31 Life As A Puzzle

Special Links:

Thanks to everyone who contributed behind the scenes to this episode: the Musical Stingers composed by Mateo Chavez Lewis, our line producer Dennis Caouki, and the theme song to our podcast with lyrics and music by Colm Molloy and sung by the one only Anne Morrison, currently on the road starring in Kimberly Akimbo.

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#27- Two "Little" Sondheim Treasure Hunts

Tue, 07 Apr 2026 15:10:00 -0000

Join Barry Joseph and guests David Spira (Room Escape Artist) and Rachel Allen Duncan (Watson Adventures) to explore why Stephen Sondheim designed treasure hunts for decades, focusing on two with related names: the 1973 A Little Night Music Treasure Hunt at the Shubert Theatre and the 2011 A Little Jurassic Treasure Hunt at the American Museum of Natural History. Performers George Lee Andrews and Marti Morris recall the Shubert cast-party hunt co-devised with Anthony Perkins, where puzzle-photo team formation led to lyric-based clues hidden around the theater. Event producer Brigid Walsh describes producing the 2011 fundraiser hunt hosted by Sarah Jessica Parker and Matthew Broderick for Friends In Deed, including wax-sealed packets, team coordinators, dinosaur-hall clue cards, a meta-puzzle, and a final reveal involving a freight elevator, toy dinosaurs, and a hidden prize.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Sondheim Human Touch

01:43 Meet The Guests

03:24 Two Little Hunts

04:55 Show And Memories

06:43 Cast Interview Begins

11:19 Shubert Hunt Story

15:49 Ice Cream Interlude

17:12 Design Takeaways

24:35 Clue Sheet Breakdown

30:43 Weddings And Hunts

32:48 Wedding Puzzle Talk

33:47 Sondheim Museum Hunt Setup

35:47 Designing the Venue

39:20 Watching Players Lose It

41:55 Why Museums Work

43:46 Dino Hall Game Ideas

46:03 Inside the Hunt Packet

50:49 Rules and Meta Puzzle

55:55 Clues and Cheating

58:44 Spoilers Final Solve

01:01:37 Prizes and Reflections

01:04:15 Sondheim Takeaways

01:06:31 Plugs and Signoff

Special Links:

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#26-Researching Sondheim--A Repod of Matching Minds on the Dr. Broadway Podcast

Tue, 24 Mar 2026 07:17:00 -0000

A conversation about Matching Minds from the Dr. Broadway podcast with Dr. Tracey Brent-Chessum and Dr. Kristin Stultz Pressley, focusing on researching Sondheim’s lifelong puzzle-and-game design—from cryptic crosswords and treasure hunts to Atari sessions with John Weidman, escape rooms, puzzle boxes, and antique board-game collecting—and on Joseph’s methods, interviews, archival work, publishing journey with Applause/Bloomsbury, and ongoing efforts to place materials in institutions like NYPL, the Library of Congress, and the Strong Museum.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Podcast Welcome

03:01 Introducing Dr Broadway

06:14 Barry’s Sondheim Journey

07:25 Games For Change Background

09:35 Atari And Game Mechanics

11:36 Sondheim Designed Games

13:18 Walls Of Antique Boards

15:03 Research Methods Archives

16:18 Pandemic Timeline Interviews

16:43 Tracking Memories Ephemera

17:04 Unlocking Interviews

18:06 Honoring Emotional Memories

18:53 Documenting And Archiving

20:49 Publishing Puzzle Theater Hybrid

23:18 New York Times Breakthrough

25:27 Research Rigor And Impact

26:52 Biggest Sondheim Revelation

28:12 Questions For Sondheim

31:21 Ongoing Projects And Farewell

Special Links:

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#25-Writing Sondheim: A Conversation with Art Isn't Easy's Daniel Okrent

Tue, 10 Mar 2026 06:44:00 -0000

Dan Okrent visits Matching Minds for his FIRST interview (woot! an exclusive) about his highly anticipated biography “Sondheim: Art Isn’t Easy” (pub. March 17). Okrent explains the project evolved from a short biographical essay into a thematic, research-heavy contemporary biography, drawing on extensive archives and interviews (including 38 people, many close collaborators), with early praise from John Weidman and James Lapine. They discuss why a new Sondheim biography is needed since Meryle Secrest’s work, why James Lapine described it as “The best that has been written about Steve,” the value of Secrest’s Yale interview tapes, and new Library of Congress material clarifying Sondheim’s account of his mother’s letter (“guilt” vs “regret”). Okrent connects Sondheim’s alcoholism, inhibition, revenge themes (notably in “Sweeney Todd”), and life arc from alienation to connection. Finally, Okrent and Barry reflect on their unusual, and quite remarkable, multiyear relationship with each other and with Michael Mitnick that supported both Art Isn’t Easy AND Matching Minds with Sondheim.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Art From Demons

00:55 Meet Dan Okrent

02:00 The Name Game

03:35 From Essay To Biography

07:39 Why Another Sondheim Book

09:26 Alcohol And Inhibition

12:23 Secrest Tapes At Yale

16:12 Sweeney Todd And Revenge

19:30 The Mother Letter Revisited

25:36 Password And Lee Remick

29:08 Writing For Insiders

29:40 Finding Your Reader

30:15 Writing for Insiders

31:43 The Missing Five Years

33:52 Procrastination or Passion

34:56 Alienation to Connection

36:13 Musicals That Connect

39:20 How Their Books Shaped Each Other

40:17 Archive Treasure Hunts

42:33 What Writing Revealed

43:53 A Collaborative Email Trio

49:53 The Creative New York Blob

51:20 Hopes and Farewell

53:23 Final Thanks and Signoff

Special Links:

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#24-Matching Minds on Broadway Nation

Wed, 25 Feb 2026 11:52:00 -0000

In this excerpt from David Armstrong’s Broadway Nation podcast, recorded at a studio overlooking the theater district, Barry and David compare their distinct, Broadway-themed, research-driven books, shared educator backgrounds, and surprising overlaps in their Sondheim publishing journeys.

Make sure to get the book everywhere books are found,⁠ ⁠⁠or click here⁠⁠⁠.

00:00 Welcome and Setup

05:09 Hammerstein and Play

06:26 Carousel Treasure Hunt

07:10 Books in Conversation

09:12 Cover Photo and Publisher

10:49 Teaching and Podcast Paths

13:39 Hidden Puzzles Revealed

15:07 Puzzle vs Game Explained

17:20 Sondheim Video Games

18:46 Sondheim Plays Myst

19:21 Distraction Or Fuel

20:58 Cryptic Crossword Legacy

21:37 West Side Thursday Ritual

23:03 Treasure Hunt Vs Scavenger

25:06 1968 Hunt Cast

26:37 Lyrics As Puzzles

28:00 Cinerama Anagram Mind

30:54 Murder Game Origins

32:30 Finishing The Hat Link

34:06 Appropriately Obsessive

35:02 Closing Thanks And Tags

Special Links:

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#23-Matching Minds at BroadwayCon with Many Guests

Thu, 12 Feb 2026 05:03:00 -0000

Come with Matching Minds to BroadwayCon in New York City during a frigid snowstorm! This episode features special guests and Broadway stars Etai Benson, George Lee Andrews, and Marty Morris, sharing their connections with Sondheim's puzzles and games. Etai recounts receiving a custom, personalized jigsaw puzzle from Sondheim for his role in Company. George and Marty take us back 53 years to share memories of the Sondheim/Perkin’s Shubert Theater treasure hunt for the cast of A Little Night Music. The audience participates in live trivia rounds (play along from home) and a reenactment of Sondheim's famous Murder Game. And suffer through our attempt at a podcast theme-song sign-a-long…

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to Matching Minds with Sondheim

00:05 Experiencing BroadwayCon in New York City

00:28 Diverse Activities at BroadwayCon

01:00 Sondheim's Puzzles and Games

01:28 Special Guests: Broadway Performers

02:41 Sondheim's Multifaceted Career

03:03 Sondheim's Influence and Legacy

04:16 Interactive Trivia and Games

05:41 Exploring Sondheim's Puzzles

09:47 Special Guests: George Lee Andrews and Marty Morris

17:26 A Visit to Steve Sondheim's House

18:05 Round Three: Word Puzzles

19:25 Round Four: Mechanical Puzzles

19:57 Special Guests: Etai Benson

25:46 Round Five: Parlor Games

26:34 The Murder Game

30:44 Conclusion: Matching Minds with Sondheim

Special Links:

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#22-Stephen Sondheim and Cryptic Crosswords

Fri, 30 Jan 2026 08:20:00 -0000

Today’s topic: Stephen Sondheim’s passion for cryptic crosswords. Joined by guests Natan Last, Katie Grogg, Ben Zimmer, and Galen Fott, the conversation explores Sondheim's 1968 stint as the puzzle editor for New York Magazine, his influence on the American cryptic crossword scene, and the connections between his musical works and love for puzzles. Through reflections on prior interviews with Richard Maltby, Jr., Will Shortz, Colm Molloy, and, yes, Sondheim himself, the episode highlights Sondheim’s legacy in both theater and the world of wordplay.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to the Podcast and Today's Topic

01:51 Meet the Guests: Crossword Enthusiasts and Experts

05:28 Discussing the New York Times Crossword Puzzle

07:51 Defining Cryptic Crosswords

10:30 Stephen Sondheim's Influence on Cryptic Crosswords

14:57 The British Cryptic Crossword Scene

22:29 Sondheim's Connection with British Crossword Constructors

32:39 Sondheim's Cryptic Crossword Journey Begins

33:33 American vs. British Crosswords: A Cultural Clash

34:41 Sondheim's Essay and Its Impact

35:44 Criticism and Parody in New York Magazine

41:34 Richard Maltby Jr. Takes Over

48:56 Sondheim's Cryptic Crossword Legacy

56:17 Modern Cryptic Crosswords and Sondheim's Influence

01:03:06 Final Thoughts and Reflections

Special Links:

Colm Molloy
Ann Morrison
Mateo Chavez Lewis
“This Time It’s Crosswords (Not Cross Words) That Surface From Sondheim” New York Times, 2011.
Galen Fott’s Blog
Natan Last
Ben Zimmer
Katie Grogg
Minute Cryptic

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#21-10 Playful Songs of Sondheim

Tue, 13 Jan 2026 22:11:00 -0000

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 rollcking conversation.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction and New Year Greetings

00:33 Special Episode Announcement

02:30 Opening with Donald Feltham

03:24 Exploring Sondheim's Unproduced Song

06:36 Evening Primrose: A Hidden Gem

09:24 Pacific Overtures: Cultural Exchange

11:42 Book Promotion and Feedback

15:35 Into the Woods: Musical Puzzles

20:22 Road Show: Life as a Game

22:15 Putting It Together: Parody and Games

28:07 Finishing the Hat: The Creative Process

30:54 Conclusion and Future Plans

Special Links:

Colm Molloy
Ann Morrison
Mateo Chavez Lewis
Sondheim's 2002 Into the Wood opening night jigsaw puzzle
Hear all the Sondheim songs at The Broadway Radio Show

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#20-Do we really need another book on Sondheim? Barry at the Drama Book Shop

Tue, 23 Dec 2025 15:52:00 -0000

Do we really need another book on Sondheim? That’s the driving question behind Barry’s recent appearance at the venerable Drama Book Shop in New York City. For the 20th episode of the Matching Minds with Sondheim podcast, explore the book-ey-ness of Matching Minds. Michael Mitnick interviews Barry in front of a live audience where together they discuss the creative challenges and the biographical insights gained during its writing.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction and Podcast Milestones

04:36 Drama Book Show Commentary

05:04 Sondheim's Love for Puzzles

08:19 Barry Joseph's Presentation

12:43 Audience Q&A and Research Insights

26:15 The Last of Sheila: A Real-Life Inspired Murder Mystery

26:42 Sondheim's Custom Puzzle for Games Magazine

28:38 Sondheim's Influence in Glass Onion

30:16 Sondheim's Treasure Hunts and Puzzle Designs

31:36 Sondheim's Cryptic Crosswords Legacy

33:14 The Emotional Impact of Sondheim's Work

36:35 Recreating Sondheim's Games for Research

38:23 Sondheim's Board Games and Auctions

41:03 Sondheim's Influence on Musical Theater

45:47 Final Reflections and Audience Questions

Special Links:

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#19-How Sondheim Gamified NYC - a talk at MCNY

Tue, 16 Dec 2025 19:01:00 -0000

Join the audience at the Museum of the City of New York as Joseph guides them on a tour of How Stephen Sondheim Gamified New York City. The talk explores the unique ways Sondheim incorporated the city into his games and puzzles. Through various anecdotes and historical references, Joseph highlights Sondheim's creative process, from his early board games to intricate treasure hunts and escape rooms. The presentation is enriched with clips from Sondheim's musicals, showcasing how his playful lens extended beyond the stage and into the real-world geography and culture of New York City. The episode emphasizes Sondheim's dual passion for theater and games, inviting the audience to experience New York City anew as an interactive playground.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction and Presentation Setup

02:26 Welcome to the Museum of the City of New York

03:15 Barry Joseph's Introduction

04:14 Sondheim's New York City Musicals

09:11 Sondheim's Treasure Hunts

12:29 Sondheim's Board Game for Hal Prince

15:32 A Little Night Music Treasure Hunt

17:26 Sondheim's Escape Room Experience

23:24 Sondheim's Cryptic Puzzles

27:57 Jurassic Treasure Hunt at the Museum of Natural History

29:11 Stephen Sondheim's Treasure Hunt Adventure

29:40 Exploring Iconic New York Locations

30:17 Challenges and Decisions in the Library

31:01 Natural History Museum: The Perfect Venue

31:27 Designing the Dinosaur Hall Puzzle

34:29 The Star-Studded Event

35:39 The Murder Game: A Meta-Puzzle

38:05 Sondheim's Puzzle Legacy

41:36 Q&A: Uncovering Sondheim's Hidden Treasures

Special Links:

Thanks to everyone who contributed behind the scenes to this episode: the Musical Stingers composed by Mateo Chavez Lewis, our line producer Dennis Caouki, and the theme song to our podcast with lyrics and music by Colm Molloy and sung by the one only Ann Morrison, currently on the road starring in Kimberly Akimbo. Of course, I'd also like to thank Nick Martinez and the whole crew at MCNY.

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#18 - About the Author - Barry on The Broadway Radio Show

Tue, 09 Dec 2025 01:10:00 -0000

From an interview with Donald Feltham on his Broadway Radio Show, join Barry on his journey writing a book on Stephen Sondheim's love for puzzles and games, spurred by birthday gifts from his wife. Barry shares how interviewing over 120 people, many of whom were Sondheim's friends and game enthusiasts, helped paint a comprehensive picture of this multifaceted Broadway legend. The episode concludes with a plug for Barry's book and podcast, encouraging listeners to explore these resources for a deeper understanding of Sondheim's playful genius.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to the Episode

01:34 Donald Feltham's Broadway Radio Show

02:29 Discussing the Book: Matching Minds with Sondheim

03:06 Barry Joseph's Background and Inspiration

03:21 The Influence of Stephen Sondheim

04:43 The Genesis of the Book

05:13 Exploring Sondheim's Life and Work

10:48 The Ludological Lens

11:21 Structure of the Book

16:43 Sondheim's Playful Side

18:11 Research and Interviews

23:16 Sondheim's Treasure Hunts

26:51 Engaging Everyone at the Party

27:04 The 2013 Treasure Hunt

29:02 Recreating the Treasure Hunt Over Zoom

31:37 The Famous Murder Game

38:36 The Last of Sheila: From Game to Movie

43:57 Sondheim's Challenging Jigsaw Puzzles

48:32 Conclusion and Podcast Invitation

Special Links:

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#17-Steve is Love: Merrily We Play Along

Tue, 02 Dec 2025 05:03:00 -0000

Steve is Love: Merrily We Play Along

Celebrate the upcoming cinematic release of Broadway’s Merrily We Roll Along with this special episode, including an interview with Maria Friedman, the show’s innovative director. Maria shares insights into Sondheim's work, his love for puzzles and games, and how her production managed to solve the notoriously challenging musical. The episode also includes reflections on the autobiographical nature of Sondheim's writing, the role of games like Hostilities in his life and work, and excerpts from the upcoming proshot film release of Merrily We Roll Along.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Cold Open

00:14 Barry's post-theme opening

05:24 Trailer for Proshot of Merrily

07:03 Barry Interstitial

08:25 Maria Friedman interview: Part 1

15:21 Barry Interstitial

18:56 Excerpt from Podcast 1 analyzing Merrily

25:47 Barry Interstitial

26:04 Maria Friedman interview: Part 2

36:09 Barry's final interstitial

Special Links:

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#16-Give us more to hear: Bonus episode

Tue, 25 Nov 2025 08:00:00 -0000

Let me give you more to hear! A bonus episode. Revisit my interview with Richard Schoch, author of How Sondheim Can Change Your Life, exploring how Sondheim's works and different analytical lenses bring out varied interpretations. Dig deeper into the promotional jigsaw puzzles for the The Last of Sheila. Listen to anecdotes from my experience with the first-ever alternative reality game, The Beast. We’ll end with reflections on publishing a new book, sharing poignant advice for aspiring authors from Richard Schoch, and highlighting how the release of my book has resonated with readers and fans alike.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 The GIve Us More episode (Podcast)

01:57 1. Richard Schock and Anyone Can Whistle

07:53 2. The Last of Sheila's Promotional Jigsaw Puzzles

33:05 5. Richard Schoch, Puzzle Boxes, and Advice to Authors with Upcoming Books

47:37 7. Broadway Radio Show Recommendation

48:14 8. Katz JCC Q&A

Special Links:

Colm Molloy
Ann Morrison
Mateo Chavez Lewis
Reality Escape Pod
Richard Schoch
The Last of Sheila production short
Bernie De Koven’s The Well-Played Game
Matthew Farber and Tracy Fullerton’s The Well-Read Game
The Grammar Girl Podcast

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#15-Sondheim: Ace Human Hacker, or Sondheim & Parlor Games

Tue, 18 Nov 2025 12:09:00 -0000

You are formally invited to my Sondheim game night party, already underway. Join previous guests David Spira, Kellian Adams, and James McCusker as we tackle and explore Sondheim's intricate world of parlor games, such as Running Charades, The Listening Game, Bartletts, Camouflage, Hostilities, and The Murder Game. Discussions touch on game history, clever designs, and the emotional nuances Sondheim orchestrated. Learn why Kellian calls Sondheim an “Ace Human Hacker” and why this is my favorite episode to date!

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to Matching Minds with Sondheim

00:57 Welcome to the Halloween Party

02:06 First Guests Arrive

04:58 Discussing Parlor Games

08:33 Exploring the Listening Game

14:23 Running Charades: Sondheim's Twist

18:26 Playing Bartletts: A Creative Challenge

27:23 Camouflage: Hidden in Plain Sight

33:57 Introducing the Game 'Hostilities'

34:38 Rules and Mechanics of 'Hostilities'

38:05 Reflecting on the Brutality of 'Hostilities'

47:11 Exploring the Murder Game

58:00 Sondheim's Approach to Game Design

01:03:24 Closing Thoughts and Reflections

Special Links:

Thanks to everyone who contributed behind the scenes to this episode, specifically the musical stingers composed by Mateo Chavez Lewis, and the theme song to our podcast with lyrics and music by Colm Molloy, and sung by the one and only Ann Morrison, who created the role of Mary in Merrily We Roll Along. And please welcome our new line producer, Dennis Caouki.

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#14-Puzzling Through Sondheim

Tue, 11 Nov 2025 08:01:00 -0000

Please join me as we revisit my guest spots on Hello Puzzler, a delightful podcast hosted by AJ Jacobs and his Chief puzzle Officer, Greg Pliska. Each week, they have a celebrity guest who appears across three episodes, and they then toss puzzles at them like peanuts to an elephant. However, to me it was more like knives to a juggler who can't juggle. I tried. Really, I tried. So today you can listen to my second and third appearance. In the first one, Greg challenged me with an inventive and hilarious Sondheim theme puzzle. I'll let him explain how it works. But all you who know the names of Sondheim songs will especially enjoy playing from home. Then in my final appearance, I get to relax and turn the tables on them. I found a number of Sondheim's own puzzles from crosswords and treasure hunts, and challenged both AJ and Greg to try and solve them. Give it a shot at home and see if you do a better job than they did at… matching minds with Sondheim.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to the Puzzle Concept

05:07 Introducing Steven Sandheim

05:26 The Twist: One Letter Changes Everything

05:40 Example: West Side Stork

06:06 Explaining the Puzzle Format

06:13 First Puzzle Challenge

Special Links:

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#13- Sondheim and Video Games

Tue, 04 Nov 2025 16:01:00 -0000

What. An. Episode! This one focuses on Stephen Sondheim's relationship with video games... sort of. This episode is hard to describe. The audio from today comes from a podcast I was a guest on by Dennis Hensley called Dennis Anyone? So is this just a re-podcast? Well, no. This is my own edit of that episode. See, this is what happened: Dennis invited me onto his podcast, then about an hour in his friend joined us. His name is also Dennis. So this episode could be called A Tale of Two Dennis. Let's call him Dennis 2. It turns out Dennis 2 was friends with Sondheim for around 35 years playing digital games with him. In fact, Sondheim would fly Dennis 2 out from LA just for weekend marathon play sessions of games like Myst and Oxyd. The thing is, Dennis 2 had never spoken publicly about his relationship with Sondheim. Even when Sondheim sent his biographer Meryle Secrest in the nineties to interview him. He never spoke about his relationship with Sondheim until this podcast episode, and it was pretty remarkable. Dennis 1 invited me to be both guest and host, so I got to interview Dennis 2 as well. As you know, my book is based on conversations with and information from over 120 people. But other than John Weidman, no one else spoke with me about playing digital games with Sondheim and how it framed their relationship. And no one shared photos with me. Until Dennis 2. It has been quite a trip! so please join me as we revisit it together.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 The Mysterious Invitation

00:43 Introduction to the Episode

01:21 A Tale of Two Dennis

01:32 Sondheim's Gaming Obsession

12:22 The Myst Experience

28:24 Sondheim's Humble Beginnings

30:10 The Last of Sheila: A Lifelong Bond

32:14 Games and Mentorship

35:49 Creative Criticism and Friendship

38:49 The Doctor is Out: A Critical Review

40:55 Sondheim's Puzzle Legacy

45:09 Reflections and Final Thoughts

Special Links:

Colm Molloy
Ann Morrison
Mateo Chavez Lewis
"Dennis Anyone?" podcast
Video of Oxyd in Sondheim’s issue of Games Magazine: https://youtube.com/shorts/A-fnPWuzU0U?feature=share
Thanks to everyone who contributed behind the scenes to this episode, specifically the musical stingers composed by Mateo Chavez Lewis, and the theme song to our podcast with lyrics and music by Colm Molloy, and sung by Ann Morrison, who created the role of Mary in Merrily We Roll Along. And SPECIAL thanks to both Dennis Osborne and Dennis Hensley!

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#12 - Matching Minds Live at the NYPL

Tue, 28 Oct 2025 06:38:00 -0000

In this special event at the New York Public Library for Performing Arts, Barry Joseph launches his new book, Matching Minds with Sondheim. The session dives into Stephen Sondheim's intricate world of puzzles and games, enriched by anecdotes from Joseph's extensive research, emphasizing the roles of research institutions in the development of the project. Attendees participate in an interactive game inspired by Sondheim, and hear from guest speakers including Richard Maltby Jr. (director and producer, lyricist, and screenwriter) and Daria Begley (writer for The Sondheim Society). Joseph shares insights into Sondheim's creative process, his love for puzzles, and his method of creating clarity and connection through games, offering a unique perspective on the Broadway legend.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction and Welcome

00:15 Introducing Barry Joseph and His Book

02:11 Acknowledgements and Special Thanks

03:00 Interactive Audience Participation

04:04 Honoring Those Who Contributed

05:37 Exploring Sondheim's Puzzles and Games

09:24 Sondheim's Unique Card Game

12:47 Sondheim's Board Games for Bernstein

19:30 Playing Sondheim's Murder Game

22:08 Insights from Richard Malty Jr.

29:17 Sondheim's Jurassic Treasure Hunt

32:07 Daria Begley's Winning Experience

36:10 Sondheim's Puzzle Philosophy

37:25 Book Release and Q&A

Special Links:

Colm Molloy
Ann Morrison
Mateo Chavez Lewis
Richard Maltby
American Museum of Natural History
Michelle King
Lost for Words: A Party Card Game of Untranslatable Feelings
The blog post about this event, with photos (including the one with Daria, her T.rex, and the audience).

Thanks to everyone who contributed behind the scenes to this episode, specifically the musical stingers composed by Mateo Chavez Lewis, and the theme song to our podcast with lyrics and music by Colm Molloy, and sung by Ann Morrison, who created the role of Mary in Merrily We Roll Along.

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#11 - Unpacking The Last of Sheila

Tue, 21 Oct 2025 07:00:00 -0000

Join us as we unpack the 1973 murder mystery film The Last of Sheila, written by Stephen Sondheim and Anthony Perkins. The discussion features guest James McCusker, a 45-year fan of Sondheim and a college composition professor. They explore the movie's origins, the unique parlor games that inspired the screenplay, and its impact on pop culture. Additional insights are provided by David Leopold from the Al Hirschfeld Foundation, highlighting Hirschfeld's unique promotional artwork for the film. The episode concludes by examining the film's game design elements and how they reflect Sondheim's creative mind.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to The Last of Sheila

01:26 Meet the Hosts: Barry and James

02:39 Origins of The Last of Sheila

05:02 Sondheim and Perkins: A Creative Partnership

13:52 The Games in The Last of Sheila

23:41 Exploring the Mysteries in Sheila

31:13 Clinton's Game and the Broken Pattern

32:23 The True Purpose of Clinton's Party

34:59 The Promotion and Press Book

36:23 Al Hirschfeld's Contribution

48:31 The Impact of 'The Last of Sheila'

53:53 Sondheim's Puzzle Design Values

57:10 Conclusion and Final Thoughts

Special Links:

Colm Molloy
Ann Morrison
Mateo Chavez Lewis
The Al Hirschfeld Foundation
Hirschfeld's Sondheim: A Poster Book
Animation from Sondheim’s notes at the Library of Congress that create a crossword grid of the actor’s names.

The Last of Sheila production short

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#10 - The Brooklyn Book Festival - It’s Puzzling: The Power of Crosswords and Games

Tue, 14 Oct 2025 07:00:00 -0000

In It's Puzzling: The Power of Crosswords and Games, host Natan Last, author of the cultural history of crosswords, Across the Universe, moderates a discussion at the Brooklyn Book Festival with Barry Joseph, game designer and author of Matching Minds with Sondheim, and Juliana Pache, the creator of Black Crossword. The conversation delves into the cultural significance of games and puzzles and how they reflect history and community. Barry shares insights from his book while Juliana discusses the creation of Black Crossword and how it connects the African diaspora through daily mini puzzles. They explore themes such as the joy of solving cryptic crosswords, the social dynamics of community-based puzzles, and the personal impacts of puzzling on their own lives. The episode also introduces listeners to the intricacies of cryptic crosswords and how Sondheim popularized them in America.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction and Book Tour Updates

01:54 Brooklyn Book Festival Panel Introduction

02:49 Meet the Panelists

04:20 The Cultural Significance of Games and Puzzles

09:05 Creating Black Crossword

11:58 Sondheim's Fascination with Games

13:38 The Intersection of Puzzles and Culture

20:00 Challenges and Innovations in Crossword Puzzles

25:55 The Everything Bagel Crossword Controversy

26:25 The Art of Clue Writing

28:38 Community and Crosswords

30:32 The Power of Black Crosswords

34:42 Cryptic Crosswords Explained

37:08 Sondheim's Puzzle Legacy

41:42 Personal Stories and Puzzle Connections

44:26 Closing Thoughts on Crosswords and Community

Special Links:

Natan Last
Juliana Pache
Brooklyn Book Festival
Locavore Variety Store
Recent talk: Interview and book reading at The Drama Book Shop
Recent talk: Playing and Composing with Graduate Students at NYU
Recent talk: Sondheim Week at the New York Public Library for The Performing Arts
Matching Minds with Sondheim: The Exhibit

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#09 - Sondheim and the 2013 City Center Treasure Hunt

Tue, 07 Oct 2025 04:03:00 -0000

Barry Joseph and guests walk through Sondheim’s final treasure hunt. Guests Kellian Adams Pletcher, a game designer at FableVision Studios, and Robert Lee, a faculty member and current chair of NYU's Tisch School of the Arts Graduate Musical Theatre Writing Program, join Barry to analyze and discuss Sondheim's love for treasure hunts. Together they explore his design of the 2013 City Center Treasure Hunt and the engaging experiences created for friends. The episode features anecdotes from participants in the 2013 City Center treasure hunt (Marty Granoff, Erin Ortman, Alexander Gemignani) highlighting Sondheim's genius in creating these immersive and fun-filled games. It also features analysis from those Joseph brought together to solve them for his book ( Andrew Parr, Jess Butler, Michael Mitnick, Mark Halpin, Richard Malty Jr.) in a half-day “re-staging”. Listen to learn more about Sondheim's playful side, his intellectual generosity, and the intricate puzzles that made his hunts legendary.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to Matching Minds with Sondheim

01:15 Meet the Guests: Kellian Adams Pletcher and Robert Lee

02:28 Robert Lee's Journey with Sondheim and Games

06:19 Kellian's Early Love for Treasure Hunts

07:56 Stephen Sondheim's 2013 City Center Treasure Hunt

11:38 The Mechanics of the Treasure Hunt

20:51 Reflections on Sondheim's Puzzle Design

34:28 Exploring Ballroom Game Formats

34:55 Debating Sondheim's Puzzle Intentions

36:50 Diving into the Clues

38:16 The Thrill of Solving Puzzles

39:49 Sondheim's Puzzle Design Philosophy

41:32 The Grid and Grill Puzzle Challenge

43:17 Inclusivity in Puzzle Design

44:37 Solving Clue Number 12

48:57 Reflecting on Sondheim's Legacy

59:35 Final Thoughts and Farewell

Special Links:

Thanks to everyone who contributed behind the scenes to this episode, specifically transcription and text editing by Jenny Westfall, the musical stingers composed by Mateo Chavez Lewis, and the theme song to our podcast with lyrics and music by Colm Molloy, and sung by the one and only Ann Morrison, who created the role of Mary in Merrily We Roll Along.

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#08 - Periodically Sondheim: His Puzzling Magazines

Tue, 30 Sep 2025 07:00:00 -0000

Barry Joseph and guest Andrew Parr page through Stephen Sondheim's passion for puzzle and game magazines. From Sondheim's early fascination with cryptic crosswords to his last major interview about puzzles, this episode uncovers how these collections provided inspiration for his works. Discover how Sondheim managed and preserved his assemblage, hear contributions from renowned puzzle creators, and explore the generational impact of Sondheim's puzzling endeavors.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction and Welcome

00:42 Introducing Tonight's Episode

01:56 Meet Andrew Parr

03:43 Andrew's Puzzle Box Journey

05:22 Connecting with Sondheim

08:13 Sondheim's Puzzle Collection

13:56 The Doyle Auction Experience

23:13 Unboxing Sondheim's Collection

25:34 Stephen Sondheim's Quest for Eye-Witness

26:41 The Significance of Games and Puzzles Magazine

28:29 Games Magazine and the 4-Star Puzzler

29:36 Stephen Sondheim's Puzzle-Solving Habits

36:55 Sondheim's Markings and Interests in Games

42:58 The Impact of Sondheim's Collection

47:08 Concluding Thoughts and Reflections

Special Links:

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#07 - Sondheim For Sale: The Doyle Auction

Wed, 24 Sep 2025 06:07:00 -0000

Join us as we revisit the historic, jaw-dropping June 18th, 2024, Doyle Auction featuring items from the collection of Steven Sondheim. The episode explores the special day through interviews by Barry Joseph with guests Grace O'Keefe, Michael Mitnick, and Pat D’Amico, who share their experiences and emotional journeys related to Sondheim memorabilia. The discussion covers the auction's catalog, its exhibit, the auction day, and the aftermath. Highlights include personal stories, bidding wars, and the unique community of Sondheim enthusiasts that emerged, spreading the iconic artist’s legacy in meaningful ways.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to Matching Minds with Sondheim

00:52 Meet the Guests: Grace, Michael, and Pat

02:36 The Auction Overview: Catalog, Exhibit, Auction, Aftermath

03:37 Chapter One: The Auction Catalog

12:22 Chapter Two: The Exhibit

18:57 Chapter Three: The Auction Begins

23:26 The Auction Room Buzz

23:59 Bidding Stories and Experiences

24:37 Online Bidding Challenges

25:47 Winning and Losing at the Auction

28:03 The Long Auction Day

29:10 Grace's Mission for Tarot Cards

31:23 The Auction's Grand Finale

32:59 The Aftermath and Community Spirit

41:17 Personal Reflections and New Beginnings

45:22 Closing Remarks and Future Plans

Special Links:

Pat’s Estate Sale 2: For the Rest of Us

Results from Sondheim auction

Full pdf of the Dolye auction lots

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#06 - Writing Sondheim: A Conversation with Richard Schoch

Tue, 16 Sep 2025 07:00:00 -0000

Barry Joseph embarks on an insightful dialogue with Richard Schoch, author of How Sondheim Can Change Your Life. The conversation delves into the emotional and intellectual processes behind writing books about Stephen Sondheim, reflecting on the personal connections and lessons drawn from his works. Both authors discuss the creation and significance of their book titles and covers, emphasizing the importance of engaging readers in meaningful ways. Richard shares poignant moments about Sondheim, including a touching story from an escape room that highlights Sondheim's desire for connection. The episode underscores Sondheim's profound impact on life and art, revealing the harmonious connections found through diverse lenses of his musicals and puzzles.

Make sure to get a copy of Matching Minds with Sondheim everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Podcast - Richard Schoch

00:00 Cold Open

00:44 Introduction to the Podcast

01:18 Guest Introduction: Richard Schoch

02:13 Discussing Book Titles

04:35 Writing About Sondheim

09:02 Research and Interviews

13:01 Exploring Sondheim's Games and Puzzles

21:21 Book Covers and Design

23:41 Inviting You into Sondheim's World

24:16 Designing the Perfect Cover

24:16 The Story Behind the Cover

26:13 Engaging with the Community

34:00 Introducing Our Books

41:45 The Emotional Journey of Writing

52:06 Final Thoughts and Farewell

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#05 - Order Out of Chaos: Sondheim and Jigsaw Puzzles

Tue, 09 Sep 2025 07:09:00 -0000

Host Barry Joseph explores the profound connection between Stephen Sondheim and jigsaw puzzles. Joined by guests Michael Mitnick, an ardent collector of Sondheim memorabilia, and David Spira, co-creator of roomescapeartists.com, the trio delves into Sondheim's metaphorical view of puzzles in relation to art. The discussion spans from the unique jigsaw puzzles in Sondheim's collection, including promotional puzzles for his film 'The Last of Sheila,' to the custom-made puzzles he gave as opening night gifts for his Broadway shows. Through anecdotes and historical insights, this episode reveals how jigsaw puzzles reflect Sondheim's intricate mind and his attention to detail in both life and art.

This is the promised link to the photo discussed in this episode of Sondheim's wall of jigsaw puzzles in his Danbury CT home.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to Matching Minds with Sondheim

00:57 Sondheim's Philosophy on Jigsaw Puzzles

01:30 Meet the Guests: Michael Mitnick and David Spira

02:04 Exploring Sondheim's Jigsaw Puzzle Collection

03:26 The Gold Boxes: The Last of Sheila

09:08 The Blue Boxes: Stave Puzzles

14:25 The White Boxes: Customized Stave Puzzles

17:38 Sondheim's Legacy and Personal Reflections

35:23 Conclusion and Credits

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#04 - Seeking Sondheim in the Stacks: Mark Eden Horowitz

Tue, 02 Sep 2025 06:31:00 -0000

Barry is joined by Mark Eden Horowitz, a senior music specialist at the Library of Congress, to explore the lesser-known aspects of Sondheim's gaming legacy that can be found in their collections. The conversation spans the new Sondheim archives recently acquired by the Library, including his music and lyric sketches, manuscripts, and rare items like personal scrapbooks. Mark shares anecdotes about Sondheim's unique board games created for friends, like The Great Conductor Hunt and Stardom, and his involvement in digital games, emphasizing his lifelong passion for puzzles and games. The episode includes an analysis of an extremely rare recording from 1968 created by Sondheim for his friend and colleague Leonard Bernstein. The episode also includes an analysis of a mysterious, unsolved manuscript from the collection, urging listeners to explore it further. This engaging dialogue offers new insights into Sondheim’s creative genius, showcasing his meticulous work ethic and multifaceted interests, and the importance of publicly-accessible research collections.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 A Moving Experience with Sondheim

00:46 Introduction to the Podcast and Guest

01:45 The State of Sondheim Archives

03:47 Exploring the Library of Congress

06:15 The Leonard Bernstein Collection

09:26 Mark's First Meeting with Sondheim

13:08 Creating 'Sondheim on Music'

16:57 Sondheim's Board Game Designs

27:07 Sondheim's Fascination with The Fool's Errand

28:53 Sondheim's Potential Career Shift to Game Design

30:23 Sondheim's Love for Video Games

33:30 Sondheim's Board Game Design for Leonard Bernstein

43:12 Exploring Sondheim's Unsolved Mysteries

45:12 Conclusion and Final Thoughts

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#03 - Puzzles and Games in the Musicals of Sondheim, Part Two

Tue, 26 Aug 2025 07:00:00 -0000

Dive deep into how puzzles and games serve as leitmotifs throughout Stephen Sondheim's musical works with host Barry Joseph and co-host Gail Leondar-Wright in this second of two parts. Joined by a panel of Sondheim scholars and enthusiasts, including Doug Reside, Julie Klausner, Ben Rimalower, and Natalie Gerber, they explore key productions such as 'Into the Woods,' 'Putting It Together,' 'Road Show,' and Sondheim's final work, 'Here We Are.' The discussion highlights Sondheim's intricate play with word puzzles, musical motifs, and the structure of his shows. From examining the metaphorical use of poker in 'Road Show' to the surreal, game-like elements of 'Here We Are,' this episode offers a fresh lens through which to appreciate the genius of Sondheim's craft.

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Cold Open

00:47 Exploring Puzzles and Games in Sondheim's Musicals

01:32 Introducing Co-Host Gail Leondar-Wright

01:57 Discussing the First Episode and Gail's Insights

03:08 Guest Introduction: Doug Reside

04:05 Guest Introduction: Julie Klausner

06:34 Guest Introduction: Ben Rimalower

09:09 Guest Introduction: Natalie Gerber

10:04 Diving into 'Into the Woods'

13:57 Sondheim's Influence from Computer Games

21:54 The Puzzle of Sondheim's Wordplay

29:22 Spinning the Sondheim-O-Matic

29:53 Exploring 'Putting It Together'

32:32 Sondheim's Self-Parody and Playfulness

33:36 The Intricacies of 'Putting It Together'

36:50 Exploring 'Road Show' and Its Themes

38:07 The Game of Capitalism in 'Road Show'

43:23 Sondheim's Final Work: 'Here We Are'

44:54 Surrealism and Puzzles in 'Here We Are'

46:50 The Ambiguity of Sondheim's Endings

59:37 Reflections on Sondheim's Legacy

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#02- Stephen Sondheim and Escape Rooms

Tue, 19 Aug 2025 07:00:00 -0000

Dive into Stephen Sondheim's love for escape rooms, examining the cultural intersections between theater and interactive games. Featuring immersive theater creator Kellian Adams Pletcher, escape room enthusiasts Lisa and David Spira, and game studies expert Nicholas Fortugno, the discussion centers on Sondheim's love for this new medium. The episode includes anecdotes from escape room designers (Michael Counts, Taylor Myers) and players who experienced games with Sondheim (Jonathan Marc Sherman), illuminating his passion and commitment to the craft. The conversation also explores the broader cultural acceptance of escape rooms as legitimate art forms and their evolutionary journey from traditional puzzles to intricate immersive experiences. This episode will also ask: Do you know what time it is?

Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠.

00:00 Introduction to Matching Minds with Sondheim

01:11 Guest Introductions

07:19 The Evolution of Escape Rooms

13:29 Taylor Myers on Paradiso and Immersive Theater

23:53 Michael Counts: The Intersection of Theater and Escape Rooms

29:46 Sondheim's Hidden Treasure Hunt

31:39 The Art of Game Design

36:56 Sondheim's Escape Room Adventures

43:09 Reflections on Escape Rooms and Art

47:44 Sondheim's Thoughts on Escape Rooms

54:12 Final Thoughts and Farewell

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#01 - Puzzles and Games in the Musicals of Sondheim, Part One

Tue, 12 Aug 2025 07:00:00 -0000

Explore the recurring theme of games and puzzles within Stephen Sondheim's work. Barry Joseph is joined by guest producer Gail Leondar-Wright and experts Eric Henwood-Greer, Mark Halpin, and Natalie Gerber, as the discussion delves into how Sondheim's love for games influenced his musicals. The episode covers various shows including 'Evening Primrose,' 'Company,' 'Merrily We Roll Along,' 'Pacific Overtures,' 'Sweeney Todd,' 'Sunday in the Park with George,' and an intriguing, lesser-known TV special, 'The Fabulous Fifties.' Each segment highlights Sondheim’s clever use of wordplay, musical motifs, and structural innovations. The episode provides a deep dive into the parallels between Sondheim’s approach to games and his meticulous craftsmanship in theatre, offering listeners a fresh perspective on his artistic genius.

Make sure to get the book everywhere books are found, ⁠or click here⁠.

00:44 Special Episode and Guest Introduction

02:24 Crowdsourcing Sondheim's Games and Puzzles

02:54 Introducing Guest Hosts

06:22 Exploring Evening Primrose

20:35 Diving into Company

25:56 Merrily We Roll Along: Games and Structure

36:21 Puzzles vs. Games: A Battle of Wit

39:13 Merrily We Roll Along: Audience Challenges

43:44 Pacific Overtures: East Meets West

48:01 Sweeney Todd: A Darkly Comedic Duel

55:25 Sunday in the Park with George: Artistic Creation

01:03:21 The Fabulous Fifties: Playground Games and Parodies

01:09:04 Final Thoughts and Farewell

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Introducing Matching Minds with Sondheim

Sun, 03 Aug 2025 18:41:00 -0000

Matching Minds with Sondheim: The Podcast in an open invitation into the puzzle-loving, game-designing mind of Broadway legend Stephen Sondheim. Based on the acclaimed book by Barry Joseph, each episode uncovers the hidden world of Sondheim’s lifelong passion for treasure hunts, cryptic crosswords, parlor games, and more. Join Barry and his guests—puzzle-makers, game designers, and Sondheim aficionados—as they explore how Sondheim's playful designs delivered moments of clarity and connection for friends, colleagues, and anyone who's ever been captivated by his genius. Whether you’re a musical theater fan, a puzzlehead, or just Sondheim-curious, this series invites you to match minds with Sondheim. Make sure to get the book everywhere books are found, or click here.

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