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:

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