It’s party time at the Playboy Mansion. And this one, to celebrate the launch of The Playboy Book, a pictorial history commemorating the magazine’s 40th anniversary, is shaping up to be a doozy. The host, eternal sophisticate Hugh Hefner, makes his entrance early, greeting many of the 200 people gathered by the pool, where pulchritudinous Playmates have been known to frolic. The booze flows freely, as does the conversation. But something is amiss. Where are the Bunnies—the fishnet, the ears, the derriere puffs? A few Playmates are making the rounds, but they are wearing cocktail dresses—and one is even accompanied by her middle-aged mother. Another drink? Too late: the bar closes at 9:30 p.m. And by 10:30, most of the guests are heading off into the Los Angeles evening. This must be an aberration. When do the legendary all-nighters take place? Replies a Playboy staffer: “They don’t.” Times have changed. From the puritan Fifties to the uptight Eighties, Hefner was an icon of libertinism, legitimizing the sexual revolution—for men, at least—with an ideology of personal and economic freedom. And Hef, as any Playboy reader knew, was the bachelor of bachelors, hedonistic, suave and attractive. But now, from his 37-room estate
in the tony Los Angeles suburb of Holmby Hills, the 68-year-old Hefner has adopted an image more in sync with the We Decade of the 1990s. As of last month, he and his 31-year-old second wife, Vancouverraised Kimberley Conrad Hefner, had been married for five years. And they have two sons, Marston, 4, and Cooper, 2. “This relationship has made my September years the best time of my life,” he says. “It couldn’t be sweeter.” Well, maybe. In a separate interview, Kimberley Hefner lets on that living with the Playboy icon has taken some adjustment. “Hef has had a lot of control over me,” she says. “But I’m breaking away from that.”
Signs of Hefner’s domestication are scattered throughout the Mansion’s 572-acre grounds. The tennis court on the west side is jammed with tricycles, Big Wheels and little red wagons, while to the north lies a children’s area where Marston and Cooper entertain neighborhood kids twice a week. And on the serpentine driveway leading up to the Mansion, a traffic sign warns: “Children at play.”
Sitting in his wood-panelled library for an interview with Maclean’s, Hefner still wears his trademark purple silk pyjamas and smoking jacket. But the pipe is gone, a casualty of his 1985 stroke, and his case-a-day Pepsi habit is now a case-a-day Diet Pepsi habit. “F. Scott Fitzgerald said there are no second acts in American lives,” says Hefner. “I’ve managed to have a third act, and it has turned out to be the most fulfilling of all.”
How he got there is intimately entwined with the history of Playboy. In 1953, Hefner, then a circulation manager with Children’s Activities magazine in Chicago, spent $600 of his own money and $10,000 more that he raised by selling shares to friends, on the first issue of Playboy, featuring a cover photo of Marilyn Monroe. It hit newsstands in December, selling 51,000 copies. With its lifestyle pieces, high-tone fiction—and nudie pictures—Playboy by 1962 had a U.S. circulation of one million. By the end of the 1960s, Hefner’s Playboy Enterprises Inc. had grown into a worldwide empire of casinos, nightclubs and movie productions. And with a circulation of more than 6 million, it was the second most popular American magazine, next to TV Guide.
But the 1980s, and an increasingly segmented market in erotica, hit Playboy hard. Even Penthouse, which had long been more explicit than Playboy, seemed tame in comparison to the new onslaught of gynecological publications and pom videos. Circulation steadily declined, down to 372 million in 1985, where it remains today. Playboy casinos in London and Atlantic City failed. And the 1980 murder of Vancouver-born Playmate Dorothy Straiten by her estranged husband took the sheen off Playboy’s ideal of carefree romanticism. Those setbacks took their toll on Hefner—and his health. “The 1980s were a very turbulent time for me and for Playboy,” he says. “And I do think that the stroke was a stroke of luck. It changed my priorities dramatically.”
In 1988, he relinquished his position as chairman of Playboy Enterprises to his daughter Christie, one of two children from his previous marriage to high-school sweetheart Millie Williams, which ended in divorce in 1959. (Christie Hefner, 41, took over the business operations—her father still is editor in chief of the magazine. Last year, the company operated in the red, reporting a loss of $13 million.) Then, after decades of liaisons with a string of Playboy models, including Canadians Shannon Tweed and Carrie Leigh, he married Kimberley Conrad, the 1989 Playmate of the Year. She was bom in Alabama, but raised in Vancouver since the age of 12. “There must be something going on in the Great White North,” Hefner says of his seeming preference for Canadian women. ‘With Kimberley,” he adds, “I realized very quickly that I had found something better than what had come before, and very clearly something better than what would be lying over the hill.” Hefner contends that marriage and children jibe with the Playboy philosophy. “It makes sense out of it all,” he says. “I’ve managed to romanticize marriage and children. To see children’s toys in the hall of the Playboy Mansion is romantic.”
Later in the day, Kimberley Hefner sits poolside, watching her children play in the water. Dressed in tank top and shorts, and sipping mineral water, the former Playmate says Hefner “is a really good father, a really good husband— he’s my best friend.” She spends much of her time, she says, with her animals: the Mansion is home to some 10 dogs, and she also operates an informal animal rescue operation to find homes for strays. Work is a thing of the past: she has not modelled since marrying Hefner. “I don’t do anything,” she says, laughing. “I’m 31.”
But life at the Playboy Mansion, she acknowledges, can be like living in a fishbowl. “People really watch,” she explains. “When we were going through our downswing—like all marriages go through ups and downs, and we’ve been going through a down for the last year—people had a tendency to treat me differently. And it’s everybody from staff to some people who I thought were good friends.” Last winter, she took the children to Colorado for a ski vacation—to the consternation, she suggests, of her husband. “Hef has his spies, though,” she adds. “I go everywhere with a security guard, so they keep an eye on me.” Across the yard, peacocks fan their tails in the bright sunshine, and from a comer of the grounds comes the mocking cry of a parrot, one of 10 on the estate. A guest comments that as fishbowls go, the Playboy Mansion is a pretty nice one. “Yeah,” she replies without much enthusiasm. “It’s nice.”
The story you want is part of the Maclean’s Archives. To access it, log in here or sign up for your free 30-day trial.
Experience anything and everything Maclean's has ever published — over 3,500 issues and 150,000 articles, images and advertisements — since 1905. Browse on your own, or explore our curated collections and timely recommendations.WATCH THIS VIDEO for highlights of everything the Maclean's Archives has to offer.