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. It goes on:
"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."
It appears to be a critical piece, especially considering captions like one that describes as drag queen as a "gay deceiver" and another in which Silverstein "hears bold new solution to population control," but Silverstein's illustrations weren't meant to harm. They were a parody of popular opinion. "Silverstein, made himself an actor in the cartoons, thereby giving them a different and maybe slightly complicated viewpoint as to where the humor lay," writes Jarry at StreetLaughter, a blog dedicated to comic stereotypes. "The cartoons lampoon and deflate the expectations of the tourist, humanizing the apparently foreign, yet for comic effect they ring new changes on those same foreign and cultural stereotypes."
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.
And as for the image of two men pushing a stroller... My, times have changed!