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Stephen Sondheim: Art Isn’t Easy

Not yet published
Expected 17 Mar 26
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320 pages, Hardcover

Expected publication March 17, 2026

39 people want to read

About the author

Daniel Okrent

27 books79 followers
Daniel Okrent's 40-year career has encompassed nearly every form of mass media. In book publishing, he was an editor at Knopf, Viking, and Harcourt. In magazines, he founded the award-winning New England Monthly and was chief editor of the monthly Life. In newspapers, he was the first public editor of the New York Times. On television, he has appeared as an expert commentator on many network shows, and talked more than any other talking head in Ken Burns's Baseball. In film, he was featured in the documentaries Wordplay and Silly Little Game, appeared in a speaking role in Woody Allen's Sweet and Lowdown, and had what he calls "a mumbling role" in Lasse Hallstrom's The Hoax. Online, he headed Time Inc.'s internet efforts in the late 1990's, and has recently given in to the dubious charms of Facebook.

But all that, he says, was either preparation for (or distraction from) what he most wanted to do: write books. Beginning with Nine Innings in 1985, and proceeding through the 2010 publication of Last Call, Okrent has been (wrote novelist Kevin Baker in Publishers Weekly) "one of our most interesting and eclectic writers of nonfiction over the past 25 years." In addition to the books featured on this site, he was also co-author with Steve Wulf of Baseball Anecdotes (Oxford University Press, 1987), and author of The Way We Were: New England Then, New England Now (Grove Weidenfeld, 1989), currently out-of-print.

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46 reviews
January 8, 2026
This was a heartfelt, witty, and in-depth survey of Sondheim's life and work. I am (as pretty much everybody knows) a lifelong Sondheim fan, but reading this book made me realize that I did not have a strong grasp on the details of his work, and how his personal life bled into it. I know and love his shows, but had no concept of the intense (and often fraught) collaborations that produced them. It was interesting to learn more about his friends, peers, and colleagues, such as: Hal Prince (and his wife Judy Prince); Mary Rodgers; Arthur Laurents; Oscar Hammerstein; John Weidman; Jonathan Tunick; James Lapine; and beyond. I knew so little about these relationships and how they impacted the work itself, so I found it fascinating.

The phrase "don't meet your heroes" could possibly also be extended to "don't read biographies of your heroes." When I was twelve or thirteen, I wrote to Sondheim to tell him that I loved his music. He wrote back "Thank you so much for the lovely note. Merry Christmas!" At the time, while incredibly grateful for his response (this letter is one of my prized possessions), I felt a little bit dejected: I'd thought he'd have more to say to a young admirer of his work (perhaps that was my own idealism and sense of self-importance at work). Upon reading this book, I'm quite glad he left it at that-not that I'd expect him to be unkind to a child, but he was predictable in his unpredictability: people never knew when he'd respond with grace or with rage. Twelve year old me (and twenty four year old me) would not have been able to handle any kind of criticism from the man who I idolized. Of course, I knew Sondheim wasn't perfect: geniuses rarely are. I knew he had a biting wit and could be defensive against criticism. But man, was he a character! The truth is, I'm grateful for this look into his personality and relationships, because it helps be better appreciate the amazing art he created despite the (sometimes self-inflicted) obstacles in his life. It reveals the struggles-personal and professional-that helped the art come into being. I particularly liked learning about the bits of himself (perhaps unintentionally) scattered throughout Company, Sweeney Todd, SITPWG, Merrily, and Passion, to name a few.

I also appreciated Okrent's acknowledgment of certain motifs, patterns, and intricacies of both Sondheim's music and lyrics-many of which I hadn't considered or realized before. I'll need to go back and listen to see if I can catch onto them now that I know what I'm listening for. While the discussion of musical specifics might not be all readers' cup of tea, I personally found it quite interesting. Sondheim's music has always been the soundtrack to my life in many ways, so understanding it-not just the words, but the point of the scores themselves-feels especially important.

Reading this book has convinced me that it might be interesting to read Sondheim's own books (the Hatbox) and maybe also the Secrest biography. So more to come, maybe. It was quite nice to read this book as part of my job (JBC review forthcoming).
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