Shel Silverstein Covered Fire Island For 'Playboy'

Feb 18

Shel Silverstein

September 25, 1930 – May 10, 1999) was an American writer, poet, cartoonist, songwriter, and playwright. Though perhaps best known for his children's books, Silverstein did not limit his audience to children. During his rise to prominence in the 1950s, his illustrations were published in various newspapers and magazines, notably the adult-oriented *Playboy*.

The beloved children's author traveled to Fire Island in 1965.

In addition to being the man behind beloved children's books The Giving Tree, Where The Sidewalk Ends, and others, author and poet Shel Silverstein also earned his keep creating cartoons for Playboy.

In 1965, before the Stonewall Rebellion, Hugh Hefner & Co. sent Silverstein to report on Fire Island's burgeoning gay scene. "Shel's most recent (and most unusual) *Playboy* assignment: to relax, as best he could, for a week at a high-camp summer resort," says the magazine in the illustrated story's introduction.

"In the last few years homosexuality as a social phenomenon has emerged from the shadows, to the extent that today there are clearly recognized gay enclaves in most big cities…. Here, sans stares, homosexuals of every stripe gayly enjoy the amenities of a thriving vacation community. And here, through this summer fairyland, strolled our straight John, bewhiskered, bare-pated, and bewildered, recording for posterity his walk on the Wilde Side."

Of course we can't know what Playboy's '60s-era readers thought of Silverstein's empathetic send-up, but one can imagine that Silverstein had a ball bouncing around what was at that time a very queer scene indeed.