A Chronological Look at Playboy’s Most Scandalous Fiction

Playboy playmates generally fit a consistent set of criteria, but the men’s magazine is far more varied when it comes to its featured fiction. With an excerpt of Lydia Davis’ buzzed new translation of Madame Bovary (out this week) advertised on the September issue’s cover as a sample of “the most scandalous novel of all time,” we decided to take a look back at some of Playboy’s most attention-grabbing literary selections.

“The Crooked Man” by Charles Beaumont – August 1955

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.”