Shel Silverstein on Fire Island

Playboy magazine during the 1960s had a candid approach to including varied social groups within its pages through the lens of artists. One feature by long time contributor, Shel Silverstein, has enjoyed lasting interest by readers and researchers for its humanistic approach to a marginalized community, openly gay men in the outskirts of New York City. In his signature light-hearted tone, prolific artist Silverstein introduced the readers of Playboy to a lifestyle that had been considered camp at best and illegal at worst, through his line drawing cartoons.

Shel Silverstein’s “Silverstein on Fire Island” appeared in the August 1965 issue of Playboy magazine. Beginning on page 119, the five page feature is presented in the table of contents as a “humor” piece and includes both cartoons from the hand of Silverstein and photographic images of the artist on location interacting with some of the people who were the subject of his drawings.

The feature contains a considerable amount of text including quotes from the people Silverstein has chosen to portray and paragraph explaining the purpose of the piece. Silverstein, as a member of the Playboy target demographic of affluent heterosexual white males, provides insight into the community of openly homosexual (exclusively male in the piece) people that vacation in a particular section of Fire Island called Cherry Grove. This expository paragraph exists as black text with a serif font and a drop cap “I” on a field of orange. The orange color is used as a background for the title blurb and as the second color besides black, for the included photographs. Of Silverstein’s thirteen drawings, ten are on a field of purple with the remaining three on a white background provided by the white of the page.

The content of Silverstein’s feature is particularly interesting considering Playboy’s place as a men’s magazine, known for intellectual articles paired with playful and sexual images of women. The August 1965 issue was published during a period of U.S. history when lesbian, gay, bisexual and transgender (LGBT) rights advocacy was finding its voice following the civil rights movement of the previous decade. Gay rights demonstrations begin as early as 1964 in response to discrimination in hiring and legal restrictions and raids on gay bars and clubs. Pro-gay organizations were being formed with rapidly increasing attendance with the decade closing with the Stonewall Riots on June 28, 1969. According to’s coverage of the Stonewall Riots the raids were part of an effort to exclude the LGBT community from public life where the “New York State Liquor Authority penalized and shut down establishments that served alcohol to known or suspected LGBT individuals, arguing that the mere gathering of homosexuals was ‘disorderly’.” Countering the mainstream view of the gay community with a humourous feature that allows a glimpse, however slanted due to the author/artist’s position as an outsider, into the joys of vacationing in an openly gay community is unusual for the time period.

Called a “high-camp community” in the feature’s expository paragraph, Silverstein’s travelogue provides a historical record of how gay men at leisure were perceived by the heteronormative public. Playboy had already positioned itself as a publication that supported a progressive approach to sexual politics and social activism under editor Nat Lehrman. Approaching a taboo subject like open homosexuality was in line with the slightly sensational tone that was being actively cultivated by Playboy.

In addition to providing cultural context for a marginalized community, “Silverstein on Fire Island” also provides a record of Shel Silverstein’s earlier work. The feature details that Silverstein had been working for Playboy for a period of eight years at the time of publication. During his over 40 year tenure as a cartoonist for Playboy, Silverstein was also publishing his many well-known children’s books including A Giraffe and a Half and Who Wants a Cheap Rhinoceros the year before the Fire Island piece. The Fire Island feature has enjoyed a lasting effect on the gay community with 21st century periodicals and blogs continuing to discuss the piece as an example of Playboy’s inclusion of the gay community. One blogger focused on gay stereotypes in comics published a post in 2008 saying that Silverstein’s “ ... 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,” supporting the assertion that Silverstein’s cartoons are interpreted as light-hearted despite problematic language native to the time period.

While the entire August 1965 issue of Playboy is saturated with illustrations, cartoons and comics that are relevant to the collection at Washington University in St. Louis’ Modern Graphic History Library, Silverstein’s Fire Island feature truly solidly belongs on its shelves as a historical record of attitudes towards a particular social community but also as an early record of a prolific and beloved artist best known for his linear cartoon style, however in the context of children’s books. It has excellent potential for those researching the history of LGBT activism in the U.S., with a potential focus on the geographical location of New York City by providing an outsider perspective, removed from the legal arguments of the courts. Of course, it also provides insight into the vacation community of 1960s Fire Island during the summer months.

“Silverstein on Fire Island” is an excellent addition to any graphic history collection for its value as a historical record of social values during a time when civil rights were being discussed everyday. Morality was being questioned daily by all walks of life and allowing the inclusion of gay men as individual humans rather than as the butt of jokes, especially over multiple pages, makes Silverstein’s feature in the pages of Playboy unique for its time and valuable to researchers today. It also carries the inherent value as entry in the timeline of work created by an artist best known for his illustrations in the far different industry of children’s books. 


  • Silverstein, Shel. “Silverstein on Fire Island,” Playboy , August (1965): 119-123.
  • Lambert, Josh. “My Son, the Pornographer.” Tablet Magazine. February 24, 2010. Accessed November 18, 2019. 26418/my-son-the-pornographer.
  • Glennon, Lorraine, et al. The 20th Century: JG Press, 2000.
  • editors, “1969 Stonewall Riots,” A&E Television Networks, updated October 4, 2019,