The Surprisingly Sex-Filled Life of Shel Silverstein

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Why you should care

Because for some lucky souls, the place where the sidewalk ends just happens to be the Playboy Mansion.

Part of a weeklong series on poems and poets, sounds and sense.

Video by Melanie Ruiz.

One of the many unexpected pleasures of the internet is Hugh Hefner’s Instagram page, where you’ll find scores of old — mostly PG-rated — photos from Hef’s personal collection, brought to life in gentle Kodachrome color (and you thought your Facebook friends’ photos made you jealous!). And among the pools, pinball, parrots and tug-of-war games with scantily clad models, you’ll spot celebrities, from Chevy Chase to James Caan to the now rather regrettable presence of Bill Cosby.

But you’ll also catch sight of another distinct figure playing croquet shirtless, a bald man with a beard you have known since your childhood — but never really known. Just what, exactly, you may wonder, is Shel Silverstein, author of The Giving Tree, Where the Sidewalk Ends and other children’s classics, doing in a highlight reel of the Playboy Mansion’s most iconic scenes? Quite a bit, it turns out, and much of it, shall we say, was not particularly suitable for the children’s hour.

Silverstein might spend weeks or months at a time at Hef’s infamous party pad.

Like the Giving Tree itself, Silverstein had a lot to offer — from cartoons to poems to songs to plays — and when he died of heart failure at age 68 in 1999, he had given his adoring fans everything up to his stump. Born in 1930 to a middle-class Jewish family in Chicago, young Sheldon was a poor student who hated conformity. After being kicked out of one college, dropping out of another and being drafted to serve in the Korean War, his prospects looked rather dim. “I didn’t get laid much. I didn’t learn much,” Silverstein later summed up his college days. “Those are the two worst things that can happen to a guy.”

So with the war behind him, Silverstein set about making up for lost time, and stimulating both his mind and body. He worked as a freelance cartoonist for a few years until 1956, when he got his big break — a job on staff at fellow Chicagoan Hugh Hefner’s young Playboy magazine. As Lisa Rogak details in A Boy Named Shel: The Life and Times of Shel Silverstein, he traveled the world as Playboy’s cartoon-drawing foreign correspondent, and his travelogue soon became the magazine’s second most popular feature, after the centerfold, of course.

And the great adventure did not end once Silverstein returned to Chicago. “For the first time in his life, women began to look his way, to flock to him,” writes Rogak. “They wanted him. Badly.” As Rik Elswit, a member of Dr. Hook, a rock band Silverstein used to write for and hang with, explained the cartoonist’s sex appeal: “Shel was not handsome. … Maybe it was his eyes; they would twinkle and pierce simultaneously, giving you the impression that he knew something you didn’t.”

Fellow Playboy cartoonist Skip Williamson likewise tells Rogak that Silverstein “knew his way around a skirt,” recalling how he and the children’s author used to walk down the street, telling the beautiful women they encountered that they worked for Playboy and asking if they would like to be a Playmate. If any of their targets expressed interest, Silverstein would pull out a measuring tape to record her dimensions. 

It wasn’t a bad life, but it could only get better when Hefner bought his first Playboy Mansion in Chicago in 1959 (the current Playboy Mansion West in Los Angeles did not open until 1971). “Being at the mansion in the middle of the night was like putting your finger in an electric socket,” Larry Dubois, a writer for Playboy, once said. “It was really alive. And Shel loved it.”

And what wasn’t to love? Hefner made his mansion a most enchanting place to visit, equipped with half-naked women, top-shelf entertainment and celebrities, swimming pools, party games, you name it. As part of Hef’s inner circle and one of its court jesters, Silverstein might spend weeks or months at a time at the infamous party pad, where he tended to lurk in the background and let others come to him. Silverstein had no patience for bores, whether they were movie stars or 34Ds, but he fed creatively off the many interesting people and encounters he had in the Playboy world — and he wrote many of his children’s works while inside it. As playwright David Mamet told The New York Times after Silverstein’s death: “He was Hugh Hefner’s sidekick, he was the great cartoonist, he lived with Hef at the Playboy Mansion, in a riot of delight.”

Silverstein had two kids and would never marry, but that riot of delight permeates all of his art, including his poems for children. Just try to read his classic “Hug O’ War,” from Where the Sidewalk Ends, without summoning those sun-drenched scenes of yore in Hefner’s pleasure garden. 

I will not play at tug o’ war.

I’d rather play at hug o’ war,

Where everyone hugs

Instead of tugs,

Where everyone giggles

And rolls on the rug,

Where everyone kisses,

And everyone grins,

And everyone cuddles,

And everyone wins.


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