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March 5, 2024

Photographs of Playboy Founder Hugh Hefner at His Chicago Mansion in 1966

Before he rose to fame in the 1950s, Hugh Hefner had served in the U.S. Army and worked in the magazine publishing industry, Playboy Enterprises said. The Chicago-born trailblazer first started circulating Playboy in December 1953 with money he borrowed from family and friends and with furniture he put up as collateral for a loan, the company said.

In 2009, Hefner told TIME he “dramatically” changed the notion of sex in America. That was one of his proudest accomplishments, he told the New York Times in 1992. “That gives me great satisfaction,” he said.

In 1966, Magnum photographer Burt Glinn embarked on an assignment to chronicle the late Playboy mogul Hugh Hefner during a typical evening at his home. Of course, an average night for the young magazine editor was anything but ordinary.

At the time, Hefner was living in a James Bond-inspired, brick and limestone mansion on Chicago’s Gold Coast. The majestic abode was not only Hefner’s home but the locus of his sex-positive brand ― a bustling salon with a near constant influx of models, celebrities, writers, artists and socialites.

Playboy’s archivist Steve Martinez provided context to accompany Glinn’s images for Magnum. He mentioned that, because of the close friendship Hefner had with Bond author Ian Fleming, the house had plenty of design choices that would delight an aspiring secret agent.

“There was a painting and you’d push a button and the painting would rise and then there would be the TV set ― and back in those days nobody had that,” Martinez said. “On the floor, there was a trap door and you’d open it and down below you’d see people swimming. Another secret door would open to reveal a fireman’s pole, which you could use to slide all the way down to the bottom floor, towards the pool.”

Architectural choices aside, the most striking aspect of Hefner’s mansion was the fact that, more often than not, it was crowded with young women in leotards and bunny ears. Hefner’s preferred lifestyle arrangement persisted when, in 1970, he left his Chicago manse to settle in Holmby Hills, Los Angeles. The former Playboy headquarters is now luxury apartments.

(Photos by Burt Glinn—Magnum Photos)


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