Charles Beaumont’s “Black Country” was selected as the first short story ever to be featured in Playboy, but it was his “The Crooked Man” that drew the most attention. The story inverted the era’s rampant homophobia by chronicling the unjust plight of a straight man trying to escape detection and persecution in a society where being gay was the standard. Although the story was originally rejected by Esquire, Playboy agreed to publish it in 1955’s August issue despite an angry outcry from readers, to which Hugh Hefner later responded: “If it was wrong to persecute heterosexuals in a homosexual society then the reverse was wrong, too.”
Switch Bitch by Roald Dahl – May 1965
Although most people associate Roald Dahl with wacked-out kid’s stories that fall somewhere between child-like imaginativeness and outright absurdism, the British writer was equally skilled at more adult-oriented fiction. The four stories that later comprised Dahl’s sex and adultery themed short story collection Switch Bitch were, quite fittingly, all written for and originally published in the pages of Playboy. The first to be published — “The Visitor” — ran in Playboy‘s May 1965 issue.
“Yossarian Survives” by Joseph Heller – December 1987
Though you can find “Yossarian Survives” in Joseph Heller’s posthumous anthology Catch As Catch Can and other collections, this short story was originally published in Playboy’s December 1987 issue as “The Lost Chapter of Catch-22.” The story stands on its own with the help of Heller’s characteristically bleak yet witty humor, but it’s better read in the context of the larger novel from which it was ultimately omitted.
“Guts” by Chuck Palahniuk – March 2004
Chuck Palahniuk’s sensationalist focus on sex and violence has made him an inescapable frat house staple, but there’s something to be said for his commitment to pushing even his own far-reaching boundaries. After causing some 40 people to faint during a book tour in 2003, Palahniuk’s then-unpublished short story “Guts” was printed in Playboy‘s March 2004 issue before being later included in his novel Haunted. At press time, Palahniuk claimed that “Guts” — an excessively violent tale about masturbation — had caused a total of 73 people to faint during readings.
The Original of Laura by Vladimir Nabokov – December 2009
The brouhaha surrounding the fate of Vladimir Nabokov’s unfinished novel — especially given the author’s instructions that it be burned after his death — understandably aroused widespread curiosity. During the bidding war over the book’s serial rights, Playboy‘s literary editor Amy Grace Loyd sent Nabokov’s agent white orchids in a reference to his novel Ada, a move that helped secure the magazine’s acquisition of the exclusive and highly controversial excerpt for its December 2009 issue.