121: Shel Silverstein on Fire Island

in “Playboy”, August 1965

I (slightly) take back some of my more perfervid declarations about “Playboy” and accusations of a general unwillingness to feature homosexuality at all in its pages (maybe it’s a prejudice on my part against tits everywhere). In 1964 Playboy explicitly adopted a policy of gay-rights, so this cartoon appears in the aftermath of that change of editorial attitude.

Shel Silverstein has such a diverse career as children’s author, songwriter and humorist that it can be forgotten that he was one of the defining spirits of the first decade of “Playboy”. His cartoons in their own comic manner exemplified the hip, modern, worldly pleasure-loving American male ethos that Hefner was trying to represent and foster.

This was a late instalment in Shel Silverstein’s cartoon travelogues. They began appearing quite early in “Playboy”. Silverstein, made himself an actor in the cartoons, thereby giving them a different and maybe slightly complicated viewpoint as to where the humour lay: in the scene, its observer or some third combination of the two. Silverstein became a slightly naïve citizen of the world, as he and the cartoons explore different and exotic cultures and scenes. The cartoons lampoon and deflate the expectations of the tourist, humanising the apparently foreign, yet for comic effect they ring new changes on those same foreign and cultural stereotypes. From travelling the world, Silverstein turned to exploring outposts of an America which had started to ‘swing’, and its new subcultures of beatniks, nudists, hippies and, in this instance, homosexuals.

Luckily today, the introduction cannot be read as mocking of homosexuals themselves. It does, however, play up a slightly shrill panic for humorous effect. And a couple of Silverstein’s own jokes in the piece are about his suddenly discovering that he is being flirted with from some unexpected corner. Which is what takes it out of the usual ”Playboy” comfort zone. There is some irony in this, since as “Playboy” cartoons, this series often featured Silverstein on the make with the native colour, laced with satirical overtones about sex and culture.

Like other pieces I’ve seen from the 60s, there is a tendency for “fagot” to be spelt with only one “g”. Go figure why?

The cartoon about rough trade and this particular type of self-loathing masochistic relationship is probably more of its time than now.

The travelogue makes the expected jokes about gay men/drag queens being women or just confused as to whether they want to be women, but Shel has the good grace to place these in the context of dialogues where he admits that he is also confused

The statement on bottom of the first page could probably have been made anytime in last forty years. And there has often been a slightly self-comforting prissy argument that being homosexual satisfies some desire to be separate and special (- this becomes a big point of debate during debates in the 70s about the homosexual community and what a fight for equality means)