In 1956, after his time was up serving with the US military, Shel Silverstein started working for a relatively unknown editor, Hugh Hefner, as a contributing cartoonist for Playboy, a far cry from the children's book author he would later become. Not only did Silverstein provide controversial cartoons, but he also wrote many satire, poems, and articles from far-flung places in his role as Playboy's international correspondent, and much more. Most of his traveling experiences made their way into his cartoons with more times than not, making himself out to be the butt of the joke. In Hawaii he sketches himself being donned in a lei by a lovely lady who says, “Aloha, sir . . . and I hope you enjoy Hawaii, sir . . . and it’s spelled l-e-i, sir . . . and I’ve heard that joke 3,227 times, sir . . .” He even did a stint with the Chicago White Sox which lead to a cartoon showing him sitting on a bench while another player says to him, “Look, if you were a pitcher, I’d rub down your arm for you. If you were an outfielder, I’d massage your legs. But all you do is sit on the bench, and I’ll be damned if I’ll . . .” Silverstein spent over 40 years contributing adult humor to those that "read the articles" in Playboy and many times he tackled very controversial issues.
In 1965, Hefner sent Silverstein to report on a burgeoning gay scene, known as Fire Island. He spent a week, relaxing as best he could, studying and immersing himself into a place where homosexuals felt safe and free to be who they were.
"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."
Silverstein had quite the ease with showing the quirky side of things, no matter the situation.
In 1965, Hefner sent Silverstein to report on a burgeoning gay scene, known as Fire Island. He spent a week, relaxing as best he could, studying and immersing himself into a place where homosexuals felt safe and free to be who they were.
"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."
Silverstein had quite the ease with showing the quirky side of things, no matter the situation.
Belonsky, Andrew. "Shel Silverstein Covered Fire Island For 'Playboy'" Out Magazine. N.p., 22 May 2013. Web. 06 Dec. 2014.