Stephen Sondheim: Art Isn’t Easy

by Daniel Okrent

Genres: Nonfiction, Biography, Audiobook, Gay, Theatre, Biography Memoir

320 pages, Hardcover

Published March 17, 2026

About the author

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.

Reviews

[Rodney · Rating 5 out of 5]

No complaints.

[Kasa Cotugno · Rating 4 out of 5]

In 1970 I fell in love, not realizing that the object of my affection had already claimed my heart via several avenues. When I first heard the broadway recording of Company, I was transfixed. then I saw a picture of Stephen Sondheim, and I was a goner. Anyone who could look like that and still have a brain capable of creating such transportive music, well, as I said, I was a goner. Only to find out later that he was responsible for lyrics to some of my favorite shows, and that he had created puzzles in the back of my favorite magazine, puzzles of such demonic complexity that sometimes even the instructions were baffling. Then he writes a movie, a murder mystery that for us anagram lovers was a sheer delight. Of course this was love of the unrequited kind, and I find I'm not alone. It seemed as if it took years for the world to discover him, but in my universe, it was as if I'd conjured him up myself. This latest exploration of Sondheim's life is well researched, but for those of us who have been fascinated from afar for decades, does not really open new doors. I did enjoy reading about his frustrating habit of not composing a note until the libretto had been finalized, but that only makes me stand further in awe. Also the fact that he found penning lyrics a chore, way in second place to the music, amazing since his phrases are so intriguing.

[Isadora · Rating 4 out of 5]

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).

[JoshD · Rating 4 out of 5]

Daniel Okrent's Art Isn't Easy, being the first serious look at Sondheim's career since his death, not surprisingly contains a good deal of new insights into the man and his career. Okrent has benefitted from access to archives made more widely available in recent years, as well as friends and collaborators feeling able to reveal and say things they likely would not have while SS was still with us. The latter, in particular, makes this a more warts-and-all portrait than anything written before. While these new insights generally reflect the book's title, and the degree to which SS was a tortured, insecure, lonely, prickly and highly self-critical creator, it's still hard to avoid the conclusion that Okrent relates some of the tales of Sondheim's tirades, hissy fits and withering putdowns with rather more relish than is entirely necessary. Which is to say that Art Isn't Easy often seems to spend more time being critical than it does appreciating Sondheim's genius. It doesn't help that, for all his research and journalistic thoroughness, Okrent is often either limited or blinkered when it comes to appraisals of Sondheim's musical legacy. He has a tendency to highlight early reviews and negative reactions - such as to the supposedly insurmountable shortcomings of Follies, or the bewildered initial responses to Passion - without fully acknowledging how, as with almost all of Sondheim's shows, their true brilliance was only appreciated later, when the world caught up with what SS was doing. He also has a tendency to buy into myths - like how it took several decades of re-writes to fix Merrily We Roll Along - that are not entirely, or even substantially true. So for serious Sondheim fans Art Isn't Easy is an intermittently illuminating, but occasionally annoying addition to the body of scholarly tomes about the master of the musical.

[Jim · Rating 5 out of 5]

I just finished Stephen Sondheim: Art Isn’t Easy by Daniel Okrent, and I honestly loved it in a way I didn’t quite expect.

What really struck me is that this book doesn’t let the musicals overshadow Sondheim’s life. If anything, it flips that. The musicals feel like windows into who Stephen Sondheim was as a person. You start to see how his relationships, his childhood, and even his struggles show up in the work—but in a way that feels natural, not forced. It made me think about shows I already know so well in a completely different light.

I also appreciated how readable it is. This isn’t one of those biographies that buries you in endless detail. Okrent clearly knows a ton, but he’s really intentional about what he includes. And because of that, the details that are there land harder—they’re surprising, sometimes a little unexpected, and often really insightful. I found myself stopping a few times just to sit with something I hadn’t known or hadn’t thought about before.

As someone who loves Sondheim, this felt less like reading a history of his work and more like getting closer to understanding him. And that, to me, made the whole experience feel personal in a really satisfying way.

[Kerry Pickens · Rating 4 out of 5]

I really didn’t know a lot of Sondheim’s music except for Send in the Clowns, but apparently a lot of people don’t either. The song was recorded about 600 times. The other reason I am not familiar with his music is he wrote West Side Story in 1957, which was the year I was born.Later he was competing with the British Invasion for listeners. What he did do was take musical theater from being bubble gum romantic entertainment to more mainstream topics. His music was edgier and he could bend rhymes like Eminem. He did write Sweeney Todd and I have seen the Johnny Depp version. On the bad side, he was a hardcore alcoholic and did not pay enough attention to his personal hygiene. He may have been autistic but he was known for being witty and condescending. He was not an observant Jew but he mainly worked with other Jews including Leonard Bernstein. He mentored a lot of young composers such as Lin-Manuel Miranda and he left funding for The Smithsonian Institution, Library of Congress, New York Public Library for the Performing Arts, the Irish Repertory Theater, and the Dramatists Guild.

[Joshua Quiñones · Rating 5 out of 5]

A comprehensive and not cumbersome biography of Broadway’s greatest composer. (That honorific reveals a bit of my bias.) While the famous Secrest biography delves into incredible detail in exploring many of Sondheim’s relationships with his collaborators, muses, and mother, this book focuses on Sondheim’s chief collaborators, mentors, and, of course, his mother. Limiting the breadth of players made it easier to follow their various narratives. This account also does not shy away from discussing Sondheim’s demons. (Easier done, I suppose, since it was written after his passing.) A great read for folks curious about “God,” as he was referred later in his career, and for those who are familiar with his oeuvre and life.

[James Loop]

sondheim and lapine rolling on ecstasy on their way to see merrily in jersey is too good

[Carol Hazard · Rating 4 out of 5]

Probably need to be a real Sondheim fan to enjoy this book. I loved it!

[Mindy · Rating 5 out of 5]

Good. Concise and readable. Learned some new things.

[Glenn · Rating 5 out of 5]

Extremely astute, terrifically fluid, appropriately appreciative. A treat.

[Scott Milliken · Rating 5 out of 5]

Anyone can whistle, and everyone should read this short (but in no way trifling) biography of a true American cultural treasure.

[Thomas F. · Rating 5 out of 5]

I don't think there are that many surprises, except maybe a little more insight into what made him choose his projects. A great short biography overall.