Matching Minds with Sondheim: The Podcast
Matching Minds with Sondheim: The Podcast
Podcast Description
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.
Podcast Insights
Content Themes
Focuses on Sondheim's passion for puzzles and games, examining topics such as the influence of games in his musicals and his interest in escape rooms. Episodes include discussions on the cultural significance of escape rooms and how Sondheim's clever uses of games are evident in shows like 'Company' and 'Sweeney Todd.'

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.
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:
“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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