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.
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:
David Armstron’s Broadway Nation
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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