A Boy Named Shel: The Life and Times of Shel Silverstein

by Lisa Rogak

Few authors are as beloved as Shel Silverstein. His inimitable drawings and comic poems have become the bedtime staples of millions of children and their parents, but few readers know much about the man behind that wild-eyed, bearded face peering out from the backs of dust jackets.

In A Boy Named Shel, Lisa Rogak tells the full story of a life as antic and adventurous as any of his creations. A man with an incurable case of wanderlust, Shel kept homes on both coasts and many places in between---and enjoyed regular stays in the Playboy Mansion. Everywhere he went he charmed neighbors, made countless friends, and romanced almost as many women with his unstoppable energy and never-ending wit.

His boundless creativity brought him fame and fortune---neither of which changed his down-to-earth way of life---and his children's books sold millions of copies. But he was much more than "just" a children's writer. He collaborated with anyone who crossed his path, and found success in a wider range of genres than most artists could ever hope to master. He penned hit songs like "A Boy Named Sue" and "The Unicorn." He drew cartoons for Stars & Stripes and got his big break with Playboy . He wrote experimental plays and collaborated on scripts with David Mamet. With a seemingly unending stream of fresh ideas, he worked compulsively and enthusiastically on a wide array of projects up until his death, in 1999.

Drawing on wide-ranging interviews and in-depth research, Rogak gives fans a warm, enlightening portrait of an artist whose imaginative spirit created the poems, songs, and drawings that have touched the lives of so many children---and adults.

Genres: Biography, Nonfiction, Biography Memoir, Music, Memoir, Books About Books, Humor

239 pages, Paperback

First published January 1, 2007

About the author

My new book Propaganda Girls: The Secret War of the Women in the OSS will be published on March 4, 2025.

Lisa Rogak is the New York Times bestselling author of more than 40 books, which have been published in more than two dozen languages. Her books Barack Obama: In His Own Words, and Angry Optimist: The Life & Times of Jon Stewart, hit the New York Times bestseller lists. Haunted Heart: The Life & Times of Stephen King was nominated for both the Edgar and Anthony Awards.

Her books have been reviewed and otherwise mentioned in the Wall Street Journal, The New York Times, USA Today, and hundreds of other publications. She appeared on The Oprah Winfrey Show as the featured guest in a show about small towns to promote her book, Moving to the Country Once and For All.

She lives in New Hampshire and is currently at work on a memoir.

Reviews

[DelGal · Rating 3 out of 5]

Fascinating man, but this wasn't written very well. I enjoyed reading most of it, but it got a bit boring and repetitive towards the end half which forced me to do some skimming which I don't particularly enjoy doing when I want to learn and/or be entertained. I personally would have appreciated having a bit more information about his childhood and more detailed discussions on his children's books too since after all most of us know him as a children's author.
Also the collection of photos included in the middle of the book could have been a bit better. More specifically, where are any pictures of the young Shel or his family?
I did like the title of this however, which pays homage to the fact that Shel never really wanted to grow up in a way.

[Marci Kay]

This book was a tough read. Somehow the author made a book about a man with a fascinating background kind of a trial to get through. The entire book seemed unconnected with one paragraph hardly making sense with the next. I kept wondering if the author had ever looked back over her disjointed notes after first writing them down. Stories and anecdotes were repeated multiple times.
Even when she would talk about some of the famous people Shel knew, it seemed like the author was name-dropping to prove how well she knew her pop culture. Why would a biography ever need name-dropping?
I would not recommend this book to anyone. Shel Silverstein is a fascinating man with a sordid history, but this was an extremely boring and confusing way to learn about him.

[Kathleen · Rating 3 out of 5]

Shel Silverstein got his start writing cartoons for the Army during WWII, and then writing more cartoons for Playboy once he left the army.

Shel Silverstein also wrote travelogues for Playboy and would spend months at a time living in the Mansion.

Shel Silverstein had a way with ~the ladies.~

Shel Silverstein was in a car crash while in Africa doing a piece for Playboy, shattered his leg, and never drove a car again.

Shel Silverstein wrote loads of folk and country music, not just "A Boy Named Sue."

Shel Silverstein wrote well over a hundred plays and spent a lot of time off-Broadway.

Shel Silverstein wrote the screenplay for a movie.

Shel Silverstein was nominated for an Academy Award.

Shel Silverstein was not just a children's book author, apparently. I highly recommend this book for anyone who finds creativity intriguing. Silverstein definitely meandered to the beat of his own tom tom, and I can't help liking this beloved childhood author even more as an adult. Excuse me, I must now track down some of this work he did for adults.

[charlotte Phillips · Rating 2 out of 5]

While the life and times of Shel Silverstein are definitely an interesting subject, the fact that this author also wrote the "Unauthorized Biography of Dan Brown" might clue you in to the weakness of her writing style. Like Brown's books, there are a lot of cliff-hanger phrases. Unfortunately these phrases are not really followed up with dramatic reveals. Luckily Silverstein manages to still be interesting even with an over-the-top treatment.

[Eric · Rating 5 out of 5]

If you enjoyed Shel's work during your life, this is a fantastic portrait of a man who was largely an enigma to his fans as well as those around him. The prose is a bit journey-man like, but the research and thoroughness that when into this work are impressive.

[Hilary Hattenbach]

Shel Silverstein was a GOD to me when I was growing up. He and Judy Blume shaped my world view and made me appreciate the whimsy and humor of life. There was a lot of interesting info in this book, tons of things I didn't know about him, but I really wish he'd written his own memoir. The fact that this book was written posthumously doesn't allow it to really capture Shel's spirit.

[Rachel · Rating 3 out of 5]

This book deserves 1 star because of the *horrible* writing, but the hugely interesting character that was Shel Siverstein automatically gave it 2 more stars. Obviously, writing a book about a man who refused to give interviews and felt his art was simply a creative job and not some profound calling is challenging, but this book was written so poorly, I doubt anyone would consider it well done.

I had no idea of the multitude of works that Shel produced (books, plays, songs, cartoons for Playboy, etc...) and I loved learning more about him. He wrote A Boy Named Sue, and Cover of the Rolling Stone...really? When he passed away in 1999, People magazine described him as a recluse who was engaged with others - a contradiction. He responded to someone who asked him what the meaning behind "The Giving Tree" was with "it's about one person who gives, and another who takes." And that was the end of the story for him. He didn't much like children, but wrote some of the most well known children's books ever made - "A Light in the Attic", "Where the Sidewalk Ends", and "Falling Up" remain classics 20-40 years after they were written.

The interviews and materials the author found about Shel would have made an excellent story - if it could have been told in someone else's hands.

[Laura · Rating 5 out of 5]

It was a slow start and honestly I did not think the writer was that great but then suddenly I was reading it like mad and I CRIED AT THE END! What a wonderful job piecing together a lot of information from the people who knew him and making the real person for us to see.
The subject matter alone sells the book for me but the author was able to recreate his spirit for all of us who wish we knew him !
For those of you who are creative types the most interesting part of this book is Shel's philosophy on life and working habits for creative folks!

[Alexa Hamilton · Rating 5 out of 5]

A fabulous, don't-want-to-put-it-down biography of a truly interesting and inspiring character. I had no idea that Shel Silverstein was so prolific in so many different fields, but I'm excited to go read, see and hear more of his work now.

[Tanaya · Rating 4 out of 5]

I never knew about Shel Silverstien's life - and it was very interesting. Not the best written book, but still fascinating. She said two websites really helped her: Carol's Banned Width (banned-width.com) & Sarah Weinman's Shel S. Archive (shelsilverstein.tripod.com).

[dirt · Rating 3 out of 5]

Shel Silverstein didn't like to ride in cars after this traumatic car accident. He walked everywhere. What a fool, he could have bought a bike with all that money.

[Joe Buck · Rating 4 out of 5]

By now, maybe it's trite to call Shel Silverstein a "renaissance man," but the label absolutely fits. From his children's books to his raunchy cartoons to his Grammy-winning songs, Shel never set root in just one field, but created in whatever medium suited his whims. The same can be said of his roving lifestyle; Shel appeared wherever he pleased, whenever he pleased, and just as easily took off for other climes when the mood struck. His work is omnipresent, yet the man is quite a bit harder to pin down, preferring a degree of privacy that - while not pure anonymity - allowed him to only go as far into the spotlight as he cared to be. He granted the occasional print interview but rarely hit tv screens (and when he did, it was most frequently on his friend Johnny Cash's show).

Author Lisa Rogak had her work cut out for her in trying to illuminate this mysterious figure... not just the biographical details, but how he preferred to live his often solitary life. In combing through archival material as well as conducting interviews with his friends, her research is impressive and helps to, at the very least, construct a timeline of events, often landmarked by his work. Rogak's writing is provides the chronology of events. She doesn't get into trying to analyze the work or contextualize it any further than Shel's own life. Looking at some of the reviews, this seems to be a sticking point for folks who are trying to judge this book by the standards of what they want it to be instead of what it is. (Also, Shel's literary estate, administered by his nephew Mitch Myers, is notoriously tight assed about utilizing Shel's work, so any kind of deep analysis would be considerably difficult to do without being able to quote the actual work.)

Throughout the book, Shel always remains slightly at a distance because ultimately the most significant parts of his life were lived inside of his head, in the privacy of his thoughts. But A Boy Named Shel does a great job of helping us trace Shel's path through the 20th century, and how such a singular talent manifested itself in so many directions simultaneously.

[Laura Cobrinik · Rating 4 out of 5]

Lisa Rogak's "A Boy Named Shel" was a partial window of the Children's Poet, Writer, Artist Shel Silverstein. While reading Rogak's book I felt embarrassed that I did not know that Shel Silverstein had ever written books for Adults, much lass that he wrote for "Playboy" magazine.

I, as a 60 year-0ld woman, and someone who worked as a Library Assistant for 20 years only knew Silverstein as that Great Children's Poet, Writer, Artist, and later a playwriter, and a singer whose works went well with music. And yes, I feel that his biggest accomplishment was the publication of his last book, "Runny Babbitt."

Rogak also showed the dark side of Silverstein in her "A Boy Named Shel: The Life and Times of Shel Silverstein." I was shocked that an person who gave such joy and laughter to children world-wide, had a hard time being around children and relating to them in person. I was very surprised about Shel's lifestyle, i.e. that he had many relationships with various women, usually lasting as "one night stands." The saddest part of the whole book was when Rogak wrote about the death of his eleven-year-old daughter. On the up side, years later it was good that Shel got joy from his second child, Matthew....

Now I know why so many three-year-old children see Shel Silverstein's "The Giving Tree" as a sad and "unhappy" book. I also see why I thought that Shel Silverstein was younger than he really was. A man with two personalities, the public more or less saw Silverstein as a person who only gave others joy and happiness. It's sad to know that Silverstein could not accept that joy and happiness from others though.

Possibly this stems from the relationship that Shel had as a young boy with his father. We even see that when his Mother dies in her 90's that Shel's life starts to deteriorate because he saw his mother as his "only cheerleader."

A sad book about a wonderful person who brought joy and happiness to thousands world-wide.
Laura Cobrinik,
Boonton Township, NJ

[Stephen · Rating 3 out of 5]

One wonders at the distribution of gifts accomplished by the Almighty in His creatures. Hedy Lamarr was not only a successful actress but also designed a torpedo guidance system used by the United States in the Second World War. Chuck Connors was not only a successful actor but also played professional basketball ((Boston Celtics 1947–48) and professional baseball ((Brooklyn Dodgers 1949, Chicago Cubs 1951). Glenn Ford was not only a successful actor but retired from the United States Naval Reserve as a full captain. Hildegard von Bingen was not only the mother superior of her monastic order of nuns but an accomplished poet, medical researcher, composer, polymath, and playwright. To the eye without benefit of divine wisdom, this seems disproportionate, in light of those many fine persons struggling to maintain a C average in high school. And then there is Shel Silverstein. His life offers another fine example of how more than a fair share of talents were manifested in one human being. He was well known as a cartoonist, mostly through his many cartoons published in Playboy magazine. He wrote hundreds of songs, one of the best known being "A Boy Named Sue" recorded by Johnny Cash. His books of children's poetry were best sellers, especially "Where the Sidewalk Ends" and "A Light in the Attic." He wrote over one hundred plays, most of them one-acts, and several screenplays. He composed four movie scores. He wrote numerous travelogues which were published in magazine form and then compiled into a book. He once wrote a song entitled "I'm So Good I Don't Have To Brag" and perhaps that aptly describes Shel. A meaningful measure of the impact of an artist is the depth to which his work penetrates its audience. I can offer some evidence of that sort of penetration. Whenever it is my turn to carry the trash to the dumpster, I recite to myself "Sarah Cynthia Sylvia Stout would not take the garbage out."

[Caleb · Rating 3 out of 5]

The book “A Boy Named Shel” by Lisa Rogak is a biography filled with stories from the interviews of people who were friends with Shel Silverstein. To understand my review you need to know a little bit more about Shel the artist, author, cartoonist and songwriter. It is the life story of Shel from when he was very young until his death. The book is filled with anecdotes and life stories told by people who knew him. It told about all of the many different places where Shel lived and gives some insight on what Shel was really like.

I would recommend this book to specific readers and I am giving it 3 stars. The Author’s tone towards Shel is positive throughout the book. The book is moderately interesting until halfway through the book when the Author seems to stretch the stories in an effort to get a couple extra pages in. In addition the Author tries to keep you on edge by foreshadowing what happens later in the book but it takes too much time to get to that part to keep you interested. This book still has a bit to offer, for instance the humour, the insight into Shel’s stories and cartoons, and a couple instances of tragedy. Another thing that caused me to give this book a poor review was that the book can be very boring. As someone who enjoys books of almost any kind this one really put me to sleep. This book is more or less of a slow going bore of a book that includes some interesting factoids about Shel.

The book “A Boy Named Shel” by Lisa Rogak was very boring. Even with the constantly rotating setting of Shel’s life stories they seemed similar and that really lost my interest. It provides some interesting facts about Shel Silverstein and has foreshadowing that raises your expectation for something that was just anti-climatic. I recommend this book to those of whom enjoy learning about Shel Silverstein and those whom like biographies.

[Jennifer · Rating 5 out of 5]

Who doesn't love Where the Sidewalk Ends?! And having been an extra in the one film he authored, I was quite eager to read more about this renowned children's author.

And, oh what I learned! Silverstein got his start by drawing cartoons for the military newspaper Stars and Striped but really started making a living off his cartoons when he was published in Playboy. Yes, you read correctly: this beloved author of children's poems found his publishing legs in the pages of a skin-mag. He wrote travelogues and drew cartoons for "Hef" for years.

While I knew he had written the song A Boy Named Sue, I didn't realize how much songwriting he had done nor how risque some of those songs were.

He may have been known for Sidewalk, The Giving Tree, and Runny Babbit: A Billy Sook but his work was extensive. He was quite a work-aholic.

All-in-all: Good bio but your view of a squeaky clean author will be altered & dosed with reality.

[Jacob Frank · Rating 5 out of 5]

Before reading this book, I was aware of Silverstein's children's books and of his work with Dr. Hook, both of which were ubiquitous throughout my childhood. I had not been aware of his deep and longstanding relationship with Playboy magazine and Hugh Hefner, his career as a hit songwriter in Nashville, or his work as a playwright. The real contribution of this book though is the way in which it fleshes out his personality, which was, to say the least, idiosyncratic. He combined the work ethic of a Picasso, the complete disregard for social norms of an Allen Ginsberg, and the philandering of a Hugh Hefner. He neither drank nor took drugs, didn't own or drive a car for most his adult life, preferring to walk everywhere, and disliked TV. He dressed like a hobo/pirate, and apparently his one weakness was a type of pudding called junket(which I had to look up). He certainly made the world a brighter place, and his work continues to do so for my daughter.

I wonder about his relationship with and opinions of other people in children's entertainment, such as Jim Henson and Dr. Seuss. I wonder if they ever crossed paths. I was interested to read that he had been snubbed at a party by R. Crumb.

Also, I wonder about the status of all of his unpublished writings. I wonder if someone is in the process of editing them for eventual release.

[Jackie L · Rating 5 out of 5]

I read this biography many years ago, but it’s always stayed with me. I think it’s because I thought of Shel Silverstein as a children’s author and that’s just not the case. I love his poems and his illustrations -he had so many talents. His poems speak to so many, I don’t know why they’re cast for children. Any parent of adult children can likely relate to one of his most famous books; The Giving Tree. It never struck me as a story for children, and it isn’t.
I think Silverstein was widely misunderstood. I believe having a child changed his perspective on life greatly. I’m torn about reading this biography as it was unauthorized. This is always a little problematic for me. But overall this is a big favorite for me and I highly recommend it.

[Dick Olsen · Rating 2 out of 5]

Shel Silverstein is presented as a man so totally immersed in his creative work that his life and his work are almost indistinguishable one from another. Sadly, however, this biography contains not one rendering of his art nor one line of poetry or prose from this cartoonist / poet / author / playwright / songwriter to make that artist-life connection. Perhaps author Lisa Rogak simply could not get reprint permission for any of Silverstein's work but, lacking actual examples of his pure talent, the biography falls flat.

[Kelly Jones · Rating 2 out of 5]

Though I was excited to read this book, I was just underwhelmed by the writing and how his life and work was explored. The timeline was unorganized and meandering, and there was repetition of details (Shel liked sushi! He was close with Hugh Hefner! He never married and never wanted to!) that distractedly wound into the narrative at random. Still, I'm glad the book exists, because Silverstein was a great oddball and should be appreciated for more than his kids books.

[Kim · Rating 3 out of 5]

This book was dry. There was no personal connection between the author and the subject. It seemed like a regurgitation of facts with no soul behind them. Also, the notes at the end didn't seem to have the author interviewing anyone. She pulled the sources from other interviews. Why not give it a personal touch and interview people who knew your subject? I just felt there was a large component to the book missing--that personal connection.

[Michael Bruner · Rating 4 out of 5]

An excellent read. It does a great job conveying how the way Shel created art and the way he interacted with the world were pretty much the same.

I found the writing style to be perfectly acceptable, the sort of prose you might expect in a magazine piece. And that seems entirely appropriate for a man who no one seemed to fully know.

[VC Bestor · Rating 3 out of 5]

When it came out, I recall thinking the ABZ Book was a bit diabolical. Now I wonder: is evil essential for creativity? Or are diabolical artists just elevated by the satanic elites lording over the media? I'm not saying Shel isn't funny; I'm saying YOU might be funnier if you were paid to be so by the powerful.

[David Macpherson · Rating 3 out of 5]

This was not a great book. It told the life of Silverstein in a very rudimentary manner. I felt that I was in a fast moving train where I didn't have time to see all the sites. WIth that said, I wanted to know a little more about Silverstein and that is what I got, so it did its job and I am grateful.

[Michael Smith · Rating 4 out of 5]

The biography of a true artist, songwriter, author, cartoonist, actor, screenwriter and his too short but fun life and work with Dr. Hook and the Medicine Show and Bobby Bare and hanging with friends like Hugh Hefner.

[The Chosen Poet · Rating 5 out of 5]

damnn what an absolute legend! while I didn't agree to everything shel did or every philosophy and/or advice he gave, I definitely learnt from him and way of living and working
makes it into the list of my top heros and peers that I look up to in the literature field

[Robin · Rating 1 out of 5]

For such an incredible story, I found myself struggling to get through this book. While it may be well-researched, the writing is poor, uninspired, and repetitive. Shel's life was full of adventure and would make a compelling book, but this isn't it.

[Kiersten · Rating 2 out of 5]

Shel seems like a wild and interesting human, but my god, the writing in this book was terrible. Repetitive, tangental, with random foreboding cliffhangers that don't get followed up on until much later. Give this one a miss.

[Korin: A Crone Running Amok · Rating 5 out of 5]

Tales from the life of an amazing man. Shel Silverstein seems to have known everyone, worked with everyone & lent a hand at everything. Things I didn't know: he wrote A Boy Named Sue, he started by doing military cartoons for Stars & Stripes, & he had two sons.

[Erin Smeby · Rating 2 out of 5]

I didn’t enjoy the writing, timeline bounced around too much. Shel lived quite a life though.