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With Hugh Hefner moving between the Playboy Mansion in Chicago, the Los Angeles studio, and everywhere else he had to go to make his empire run, he needed to travel in style. So he purchased the Big Bunny, which he bought and retrofitted after a 1966 trip to London. Hef’s taste for the extravagant was on full display – as well as his flair for branding. He demanded, for example, that the plane be painted all black. The Jet Bunnies had their own special uniform, which was on full display in the Miss November 1970 pictorial, starring Jet Bunny Avis Miller (and current playboy employee Pat Lacey).

The Big Bunny cost him $5.5 million in the late ‘60s, which would be about $38 million today. Hef’s description of the jet from his January, 1974 Playboy Interview paints quite a picture.

Hef’s personal flight crew, the Jet Bunnies.

“The plane is a logical extension of the concept behind the house: We ordered a stretched version of a DC-9 from Douglas Aircraft, with additional gas tanks to give it international capability, and had a custom interior designed that turned it into an airborne apartment,” he told playboy. “In that way, whatever time is spent in transportation isn’t wasted, since I can do anything aboard the Big Bunny that I do in the Playboy Mansion. Well, almost anything. We don’t have a swimming pool or a bowling alley on the plane.”

His housing, too, was the subject of much consideration. He maintained, initially, an apartment atop the playboy office building in Los Angeles, but wanted something more palatial. So he bought Playboy Mansion West, a property set on five-and-a-half acres and just a block-and-a-half from Sunset, spotted by his then-girlfriend Barbi Benton.

“I don’t think anything I could say would adequately describe the place,” Hef said. “The main building was inspired by a mansion in England called Holmby House; it’s built of stone, with slate roofs and leaded windows. The grounds are handsomely landscaped, with rolling hills, a variety of trees, plants and flowers and what is reputed to be the largest redwood forest in Southern California. We added a tennis court and a swimming pool, with adjoining ponds and waterfalls, and introduced exotic varieties of fish, birds and animals as a finishing touch. It isn’t as large as the Chicago Mansion, but it’s even more impressive because of the elegance of the architecture and the grounds. There’s a separate guesthouse, a green house and a game house, with an outdoor bar and buffet area done in the same stone as the main building. But the most popular spot on the estate is a grotto we built, as a part of the pool, that can be entered by swimming through a waterfall and includes an elaborate series of Jacuzzi baths that are enjoyed more as a center of social activity than for their therapeutic value. In short, the West Coast Mansion is a veritable Shangri-La, and rumor has it that you really do start aging perceptibly after leaving the grounds.”

For all his jetset lifestyle, he was about to take a small turn towards the domestic. Playboy After Dark required that Hef have a beautiful companion to accompany him during his hosting duties. The first, an 18-year-old from UCLA, was Barbi Benton. He asked her out after just two episodes.

“I don’t know, I’ve never dated anyone over 24 before,” she told the then-42-year-old Hefner.

“That’s all right, neither have I,” Hefner said.

Barbi Benton on the cover the May 1972 issue.

The pair were inseparable for years, flying around the country and world as Hef enjoyed the relationship and his expanded empire. Barbi featured on the cover of the magazine four times: July 1969, March 1970, May 1972, and December 1985. She also appeared nude in the December 1973 and January 1975 issues, though she was never a Playmate.

The Playboy Casino in London, opened by Victor Lownes, quickly became a huge part of the playboy brand, briefly becoming the most profitable casino in the world. The magazine featured the club as part of its “Playboy on the Town in London” photo feature that ran in December 1966.

Though Playboy was riding high, Hef soon faced challenges from both women’s groups and magazines resulting from relaxed obscenity laws after the 1969 Supreme Court ruling in Stanley v. Georgia that allowed Americans to look at whatever they wanted in the privacy of their own home. Robert Guccione’s Penthouse took that as a cue to make the leap across the pond in spectacular fashion. The magazine had been founded in 1965 in Britain, but didn’t pose a challenge until they took out a full page ad on the back of the New York Times announcing their intention to take on playboy. “We’re going rabbit hunting,” the full-page ad read, complete with a crosshair over the iconic playboy rabbit.

playboy is playing Rome to our Hannibal,” Guccione told New York magazine. “Bringing Penthouse into the U.S. was like bringing elephants over the Alps — it was a feat of comfortable difficulty.”

Penthouse’s largest innovation was featuring pubic hair, which put the pressure on playboy to follow suit. The magazine did so in January, 1971, when it featured Norwegian girl Liv Lindeland with the barest hint of pubic hair poking from between her legs.

But Hef couldn’t worry about Penthouse. He had to deal with widespread women’s protests against the magazine, contending that playboy was in the business of objectifying women. Those protests came to a head when feminist writer Gloria Steinem went undercover as a Bunny in the New York Playboy Club. Her two-part expose in Show Magazine in May and June of 1963 painted a bleak picture of poor working conditions, sexual harassment, and overall bad feelings.

The show recreates the dramatic interaction between that Hef and Steinem, where Hef (who had cast himself as the face of the sexual revolution) tried to defend himself first in print, in an interview in McCall’s. “What Playboy Doesn’t Know About Women Could Fill a Book,” was the headline of the subsequent piece, which saw Hef seeming out of step with the increasingly active women’s lib movement.

As the show points out, his foray into televised debate went just as poorly. Hef went on the Dick Cavett show to debate Susan Brown Miller and Sally Kempton in the 1970s.

“[Men] oppress us as women. They won’t us be. Hugh Hefner is my enemy,” Susan Brownmiller told Cavett, before daring Hef to come onstage wearing a cotton bunny tail.

“I’m more in sympathy than the girls realize…” Hef said.

“Women,” Brownmiller corrected him. “I’m 35.”

“I’ve used girls to refer to women of all ages.”

“You should stop.”

Still, the magazine continued to grow and change. Penthouse wasn’t done with their challenge and Hef had to face that head-on.

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