Being a writer, I am sometimes asked my favorite poets, and I reply Elizabeth Bishop, William Butler Yeats, Robert Lowell, and my all-time favorite … Shel Silverstein, who died this week (May 10) in 1999. The first three poets are profound; Silverstein is clever.

Silverstein once told an interviewer that as a young man he would rather have played sports and chased girls, but being bad at both, he settled on drawing and writing. He began submitting cartoons to various magazines before becoming a traveling cartoonist for Playboy magazine, drawing cartoons – most of which included his self-caricature – based on his impressions of the places he visited, including a nudist colony in New Jersey, Haight-Ashbury hippies in San Francisco, and a Swiss village, in which he joked in a cartoon, “I’ll give them 15 more minutes and if nobody yodels, I’m going back to the hotel.”

Then an editor at Harper & Row took a chance on a children’s book Silverstein wrote and illustrated. “The Giving Tree” was about the life-long relationship of a young boy and a tree, and it became a bestseller, although the boy often cruelly exploits the tree, which made many readers uncomfortable.

But it was Silverstein’s later books, “Where the Sidewalk Ends,” “A Light in the Attic” and “Falling Up” that endeared him to many millions of children and their parents. The illustrations are delightful, and the short poems are brilliantly clever, including my two favorites, “Longmobile” and “Drumstick.” They go:

“It’s the world’s largest car, I swear. / It stretches from Beale Street to Washington Square. / And if you get in to go where you’re going, / You simply get out, ‘cause you’re there!”

And: “I only had one drumstick at the picnic dance this summer. / Just one little drumstick, they say I couldn’t be dumber. / One tough and skinny drumstick, why is that such a bummer? / But everyone’s mad at me, especially the drummer.”

Arguably Silverstein’s most famous cartoon depicted two prisoners chained to a wall, their hands and feet shackled in irons, with no hope of escape. “Now here’s my plan,” one says to the other.

“Lots of people said it was a very pessimistic cartoon,” Silverstein said, “which I don’t think at all. There’s a lot of hope even in a hopeless situation.”

He should know. He is a Grammy winner and Oscar and Golden Globe Award nominee, and is in the Nashville Songwriters Hall of Fame (for his hilariously clever song “A Boy Named Sue,” sung by Johnny Cash) and the Chicago Literary Hall of Fame. Not bad for a guy who was hopeless at playing sports or chasing girls, but found hope in cleverly caricaturing the world.

See what people are talking about at The Community Table!

Thank you for reading!

Please purchase a subscription to continue reading. If you have a subscription, please Log In.