When it turned out that was taken, he came up with Playboy. He originally gave his magazine the crude name Stag Party. Hefner’s greatest contribution as a cultural figure was serving as a bridge between those eras. They were simply interrupted by the Great Depression and World War II, the difficult years of Hefner’s dissatisfied boyhood. The 1960s are remembered as America’s decade of sexual and cultural liberation, but those trends began in earnest in the 1920s. For founding a magazine devoted to sex, cocktails, art, stereo equipment, and literature in 1953, Hefner was often considered a man ahead of his time.īut in fact, he was a bit of a reactionary.

Hefner devoted his career to restarting that party. “There is no way to underestimate the effect movies had on me as a boy,” Hefner once told the Tribune. “My dreams came alive at the Montclare Theater.” He would remember watching “all those images of the Jazz Age, the flappers … and thinking that I’d missed the party.”

Grand Ave., watching glamorous Hollywood musicals and dramas, which were meant as an escape from the dreary privation that descended on America in the 1930s. (Hefner remained so fond of Steinmetz that in the 2010s, he donated $7,500 a year to print the school newspaper, the Steinmetz Star.) As a boy, he spent his Saturday afternoons at the Montclare Theater, 7133 W. New England Ave., in the Galewood neighborhood, attending Sayre Elementary and Steinmetz High School. Chicago was speakeasies and jazz and gangsters, the town that, in the words of a song written in that era, “Billy Sunday couldn’t shut down.” Choreographer Bob Fosse, Hefner’s exact local contemporary, tried to recreate that racy city in the musical Chicago, and Hefner tried to recreate it in Playboy. Ernest Hemingway, then the most famous figure in American literature, was from Oak Park. When Hefner was born, in 1926, Chicago was the city of Louis Armstrong and Al Capone. The Playboy Philosophy, Hefner’s megapart manifesto of male liberation, expressed the longings of a square young man who grew up in a square big city.Ĭhicago hadn’t always been squaresville, though, and Hef knew it. While the Midwest may seem like an unusual birthplace for a magazine that came to be called “the Bible of the sexual revolution,” Playboy’s style and ethos were very much influenced by the city’s culture and history. Its Spring 2020 issue will be the last before it goes online-only. A relic of an era when pornography could only be found on paper, Playboy kept publishing only due to the sentimentality of its founder, Hugh Hefner, who died in 2017 at age 91.

The magazine, which last year became an ad-free quarterly costing $25, was losing $5 million a year. Playboy magazine died last week, at age 66, of complications related to the novel coronavirus.

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