You Know His Books, But Here Are 6 Things You Didn’t Know About Shel Silverstein

There are some books that just last for generations, and are loved no matter when they are read. Shel Silverstein has created so many of these books. His ability to tell a sweet story in just a sweet poem or short book is practically unparalleled. He is still one of the best children’s authors (at least in my opinion) but there is a lot more to him than that. Whether you were a fan of The Giving Tree, Falling Up, or any of the other books he released over the years, you may not have realized that his career didn’t start in children’s books.

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You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

1. He started his career in an unexpected way

It was actually the exact opposite. His first big job drawing cartoons was for Playboy! He met Hugh Hefner back in the 50s when he was working freelance. Hefner commissioned a few cartoons from Shel and then they continued to work together for over 40 years.

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You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

Silverstein was an interesting man who was a lot more than just a cartoonist and children’s writer. He was something of a controversial figure because of his “playboy” reputation. At the very least, you can see he managed to live an interesting life.

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You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

2. Did you know he wrote songs for Willie Nelson?

You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

When he wasn’t writing books or drawing cartoons, he helped write classics like Johnny Cash’s “A Boy Named Sue”. He also wrote songs for Loretta Lynn, Willie Nelson and even Meryl Streep! The song Streep sang in the movie Postcards From The Edge called “I’m Checking Out” was actually nominated for an Academy Award!

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3. He was particular about how his work was presented

You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

Silverstein was very concerned about the type of paper and book that his work was displayed in. He would only work with publishers that allowed him to choose the type, size, shape, color and quality of the paper for the book. If you have ever owned a Shel Silverstein book you know that there is something special about them.

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4. He was in the army

Silverstein was drafted into the United States army and served in both Japan and Korea. He actually had a whole bunch of comics about the army in his first book Take Ten.

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You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

5. He never read reviews of his work

You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

He told Publishers Weekly that ” I think that if you’re creative person, you should just go about your business, do your work and not care about how it’s received. I never read reviews because if you believe the good ones you have to believe the bad ones too. Not that I don’t care about success. I do, but only because it lets me do what I want. I was always prepared for success but that means that I have to be prepared for failure too. I have an ego, I have ideas, I want to be articulate, to communicate but in my own way.”

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6. He hated happy endings

You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

It’s pretty obvious if you read some of his work that happy endings are really not his thing. He once told the New York Times that happy endings “create and alienation.” He explained that “The child asks why I don’t have this happiness thing you’re telling me about, and comes to think when his joy stops that he has failed, that it won’t come back.” By writing stories that aren’t the stereotypical endings at least they don’t feel as bad.

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You Know His Books, But Here Are 6 Things You Didn't Know About Shel Silverstein

Even though Silverstein passed away in 1999, his books will live on forever. Share if you remember reading his work when you were young!

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Emma C
Freelance Writer