Shel Silverstein’s Best Books

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If you were lucky enough to be read to as a kid, you probably found yourself face to face with Shel Silverstein, whose iconic bald head appears on the backs of most of his books.

He sports a chipped front tooth on “The Giving Tree" and bare feet and a guitar on “Where The Sidewalk Ends.” By “Falling Up,” Silverstein’s beard contains more salt than pepper. His pose changes, his wardrobe evolves — poet’s blouses making way for shirts open one button too far — but, over three decades of stories and poetry collections, the intensity of Silverstein’s gaze remains the same.

To appreciate his laser focus on the full gamut of kids’ lives, these pictures are a good place to start. But to understand how Silverstein became what Leonard S. Marcus described as the “troubadour king” of children’s literature, we need to zoom out a bit.

“Shel Silverstein is more or less divided into three parts,” Richard R. Lingeman wrote in a 1978 profile. “There is the part known as Uncle Shelby, Playboy magazine cartoonist, versifier and perverse fabulist. There is Shel Silverstein, singer-composer, who writes songs for such country music performers as Loretta Lynn and Johnny Cash (who recorded Mr. Silverstein’s biggest hit, ‘A Boy Named Sue’). Then there is Shel Silverstein, children’s book author.”

By the time Silverstein died in 1999, at 68, his songs had been recorded by Judy Collins, Marianne Faithfull and Waylon Jennings. He’d written a number of plays and movies, including one with David Mamet. He’d cartooned not only for Playboy but for Stars and Stripes, the official newspaper of the U.S. military.

Tempting as it might be to deify him — creative genius! gone too soon! — Silverstein won’t allow it. Spend some time between the covers of his books and the man will remind you, again and again, that he was the sum of his era and his imagination: witty and wacky, quixotic and melancholic, equal parts jaded and hopeful and louche. Remember that friend of your parents’ who treated you as if you had something interesting to say? Who spoke in a way you understood, with a tantalizing hint of the inappropriate? That’s how Silverstein wrote for kids.


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