As a child I adored Shel Silverstein’s books, The Giving Tree and Where the Sidewalk Ends, among others having a special place in my heart. In fact, I think I treasure them now more than I did when I was a little girl. I always had an inkling Silverstein did more than write children’s books and my inkling proved true when I read Lisa Rogak’s biography A Boy Named Shel.

To call Silverstein a Renaissance man is putting it mildly. Not only was he a prolific children’s author, he was also a cartoonist, singer/songwriter, screenwriter and playwright. He also led a rather interesting personal life.

Born to a Jewish family and raised in Chicago, Silverstein attended Chicago School of the Fine Arts but was soon drafted into the Army. While in the Army Silverstein began to draw cartoons and later, once he returned to Chicago, he drew and published cartoons for several magazines.

But it is after he began to get his cartoons in Playboy when Silverstein’s multi-layered career really began to shine and lead to greater success. He also began to write songs, mostly of a folk variety and formed his own folk group. But one of his most famous songs is the country/novelty song “A Boy Named Sue,” which became a huge hit for the late Johnny Cash. Silverstein’s songs were also sung by Judy Collins, Dr. Hook, Marianne Faithfull and Emmylou Harris. Silverstein co-wrote many songs with Kris Kristofferson and Waylon Jennings, both remained lifelong friends with Silverstein.

Silverstein also wrote a great deal of scripts for the stage, film and television at times co-writing scripts with others, including David Mamet. One of the most popular television programs Silverstein wrote for is the Generation X classic “Free to Be…You and Me.”

Professional success led to personal success, especially when it came to the ladies. To put it bluntly, Silverstein was a playa, and many of his experiences as a playa were due not only to his success, but to him hanging out a great deal at the Playboy Mansion. Despite being a bit of a man ho, many of his carnal conquests remember him fondly for when he was with a woman he really made her feel special and he was often honest with them, claiming he was not the type to settle down.

Still, Silverstein did have children, a daughter and a son, and though he loved them he wasn’t exactly the ideal father. And as I read A Boy Named Shel, I learned as much as Silverstein was revered by the children who read his books, his relationship with children (both is own and those of his friends) could be described as complicated.

In fact, complicated pretty much sums up Silverstein as a human being and a creative individual. At times he was a total bon vivant, the life of the party. At times, he was very reticent and private. He was meticulous when it came to his writing and drawing, but often dressed like a homeless person. When it came to his children he experienced both tragedy and triumph. He could be both kind and cruel.

And other tidbits I learned about Silverstein included eschewing driving after being in a bad car accident. He was nominated for an Oscar. He wrote travelogues and was quite the globetrotter. And he lived all over the country.

All of this living in one life should have made A Boy Named Shel a scintillating read; but as I kept reading this book, especially as I neared the end, I found myself bored. Rogak writing style is dull and lacks a certain punch that keeps you wanting to learn more and more. She is way too repetitive and dry, which I soon found rather insulting to Silverstein’s legendary legacy and his output as a truly original artist that entertained audiences for decades and continues to entertain nearly twenty years after Silverstein’s death. Perhaps, this book would have served better as an article. In the end I just mourned that Silverstein never wrote his own memoir.  Now that would have been a book.

Still, I am grateful I learned more about Shel Silverstein. I will never stop loving those children’s books that delighted me as a bookish little girl, and am now inspired by Silverstein’s creative output to sharpen myself as a Renaissance woman. Perhaps, if you read A Boy Named Shel and connect with his work
, you, too will feel inspired.

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