Stephen Sondheim: Art Isn’t Easy

by Daniel Okrent

A revelatory look at the complex inner world of one of the twentieth century’s most beloved theatrical composers

Stephen Sondheim (1930-2021) was a towering figure in American musical theater. Celebrated for such iconic Broadway shows as Company, Sweeney Todd, and Into the Woods, his accolades include eight Tony Awards, multiple Grammy Awards, an Academy Award, and a Pulitzer Prize. In this intimate biography, Daniel Okrent follows Sondheim through the tumult of his upbringing and his parents’ divorce, his life-changing relationship with Oscar Hammerstein II and subsequent immersion in musical theater, and his rise to fame as both a lyricist and composer.

Okrent shines new light on Sondheim’s complicated emotional life, wavering self-confidence, and alcoholism, drawing on the artist’s intimate correspondence with such notable figures as Hal Prince, Leonard Bernstein, and Arthur Laurents; exclusive interviews with his close friends and collaborators, including James Lapine and John Weidman; and Sondheim’s own oral history, which remained closed until his death. He also reveals a previously unknown (and crucial) aspect of the infamous letter from Sondheim’s mother that made him believe she regretted his birth. As Okrent explores the ways Sondheim’s music and lyrics express the inner man, he shows us a life that was defined by two parallel the movement from alienation to connection, and from ambivalence to resolution.

Genres: Nonfiction, Biography, Theatre, Music, Audiobook, Gay, 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.

[Richard · Rating 5 out of 5]

Instead of writing a hagiography, Okrent manages to balance a focus on Sondheim’s prolific work output and perception as a “God” of musical theatre with painting a portrait of the man himself. Sondheim doesn’t come across as a saint. He drank and did drugs, clashed with his difficult mother, and bristled at criticism. Love came to him late in life and mellowed him. As a lifelong fan of his work, I feel I know what he was like in life a little bit better, which is the mark of a truly great biography. A must-read for Sondheim fans. I read part of the book in hardcover and listened to the Audible version for part. Okrent reads the book himself and does a really nice job keeping it sounding conversational and engaging.

[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.

[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.

[Daniel · Rating 5 out of 5]

More of a booklength essay than a definitive biography, it is a wonderful tribute to one of the greatest composer/lyricists in theater history. Perhaps the best thing I can say is that while he does not pull back from dealing with Sondheim's dark side, you come to the end of the book filled with admiration for the man. As someone who has been a fan for decades -- and saw at least some of the original productions of his shows -- I highly recommend it.

[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).

[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.

[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.

[Glenn · Rating 5 out of 5]

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

[Mindy · Rating 5 out of 5]

Good. Concise and readable. Learned some new things.

[Michael Reilly · Rating 4 out of 5]

This is the most recent book in the Yale University Jewish Lives series. They have done a great job of matching talented writers with significant Jews. There are over a hundred biographies in the series. I enjoyed many of them, for example, Jeffrey Rosen on Louis Brandeis, Lee Seigal on Groucho Marx, Adam Philips on Freud, Mark Kurlansky on the baseball player Hank Greenberg, and Adam Begley on Houdini.

I am not a big Sondheim fan. I never saw one of his plays live. I have seen broadcast versions of a few of them. I know a few of his songs. I have heard him described as the most important influence in American theater between 1960 and 1990. Highlights of his career include writing the music and lyrics for "A Funny Thing Happened on the Way to the Forum", "A Little Night Music", "Sweeney Todd", and "Sunday in the Park with George" and the Lyrics for "West Side Story "and "Gypsy".

On one level his life wasn't that exciting. He lived in the New York theater world. He spent most of his time in his apartment writing music and lyrics. He was married once very late in life to a young man. His social life seems to have been mostly going to high society NY parties, galas and award ceremonies.

Okrent is a big fan, but an honest biographer. Sondheim was a brilliant man. From an early age, everyone knew that he was really smart. As a teenager he became enamored of musical theater. Oscar Hammerstein, of Rodgers and Hammerstein, was a family friend. He took the teenage Sondheim under his wing. Sondheim frequently described Hammerstein as the most important influence on his life. He said the if Oscar had been a geologist, he would have been a geologist.

Sondheim was a very difficult guy to get along with. His life was punctuated with feuds, arguments and verbal fights. He would hold a grudge over a bad review for forty years. Like many brilliant people he could be charming and witty when he chose to, but that was not his normal affect. Most people, even friends, were afraid to approach him at a party. He approached you.

Sondheim had a horrific relationship with his mother. She never forgave her husband, his father, for divorcing her. She was a shrewish, difficult and insecure person. She battled with her son for her whole life. Even though he supported her financially for years, they couldn't be in a room together without fighting.

This is the most horrific thing I ever heard a mother say to a child. Sondheim claimed that his mother sent him a letter that said, "the only regret I have in life is giving you birth.".

Sondheim was also an alcoholic during most of his life and a serious drug user. He amazed his friends with his ability to function after so many drinks and drugs.

Sondheim loved writing music. He loved taking an idea and turning it into a musical play. Okrent dies a wonderful job of showing the price that Sondheim was willing to pay for those pleasures.

[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.

[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.

[Sean · Rating 5 out of 5]

I've read A LOT of Sondheim biographies (just like I've seen A LOT of Sondheim musicals). Most deify him -- which never seemed to track for me, given all the brilliant assholes at the core of each musical. It's SO REFRESHING to read one that picks at his bitchy, bitter dark side.

Loved the anecdote of Larry Kramer proposing they write a musical together -- and Sondheim replying that he doesn't 'do' political. Or Sondheim calling out Jason Robert Brown for not saying "I loved it!" after he went backstage following a performance of 'Putting it Together' (Brown is grateful for the moment, saying it taught him that great art -- which Sondheim creates -- can only be born of deep vulnerability.)

Also -- 'Sunday' was written in marijuana smoke. 'Into the Woods' with bowls of cocaine. Ah yes, it all makes sense now...

[Will White · Rating 5 out of 5]

I'm a Sondheim-is-God person and I read every Sondheim book, so in a way I'm parti pris. Having read every Sondheim book though, I can say very confidently that this is a good one, even for someone who's read them all. Lots of new stuff that hasn't been written about anywhere else, with good source citations. But I would also think that this would be a great starter biography, because it doesn't go into too much depth on any of the musicals or any element of Sondheim's life.

It's just a neat little Sondheim book and I really enjoyed reading it.

[Garry · Rating 5 out of 5]

I'm not a big fan of Broadway shows or Sondheim's work beyond West Side Story, A Funny thing Happened on the Way to the Forum, A Little Night Music and Sweeny Todd. Sondheim comes across in this biography as prickly, hard to work with and more than a little unlikeable. And, a genius in a field of music I barely understand.

[Rusty · Rating 5 out of 5]

A terrific read. I thought by now that I knew all the "Steve stories" and was delighted to come across many I had never heard before. Well written and researched - a must for fans of Sondheim or of the musical theater.

[Chrissy]

Every time I finish a Sondheim biography I’m left wondering if there is any footage from the Yale production of “Frogs” - the musical that incorporated the swim team and took place in an Olympic size swimming pool 🐸

[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!

[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.

[Ellen · Rating 4 out of 5]

Audio book. My first immersion. Genius doesn’t make a perfect human.

[Campbell Andrews · Rating 4 out of 5]

A towering artistic life, a personality marked by pettiness and vulnerability. Mr. Okrent makes Stephen Sondheim so relatable that I truly believe he might have switched places with somebody like me.

[Donna RB]

If you love his work- the details are fun!

[Justin · Rating 5 out of 5]

Essential reading for anyone with an abecedarian understanding of musical theatre and above.

[Jana · Rating 3 out of 5]

Started out like pretty much every other Sondheim biography that's ever been written, but there were some new (at least to me) stories at the end.

[Lauren Grill · Rating 4 out of 5]

and you think of all of the things you’ve seen, and you wish that you could live in between. and you’re back again only different than before.

[Nourah · Rating 5 out of 5]

Ah

[Cynthia · Rating 1 out of 5]

The more I read, the more I disliked Sondheim. I found it discomfitting to read such an unflattering depiction of the protagonist.

[Tim Grimes · Rating 5 out of 5]

Excellent biography of the famous composer with insights into his creative process