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"I still pick the covers, still pick the centerfolds, still pick the cartoons, the party jokes, edit overall pacing of the book and what goes into it," Hefner says. "I'm probably the oldest working editor of a major magazine in history, I imagine.
"About six months ago I started Twittering," he adds, about to repeat his favorite new joke. "I used to be a jitterbug, now I'm a Twitter-bug."
Last year his estranged wife, Kimberly Conrad, threatened to sue over his selling of her house; Hefner later settled "by giving her more money." His three original live-in girlfriends from The Girls Next Door are long gone, and two of their replacements, the Shannon twins, were invited to move elsewhere. With Harris, he is down to a single female companion for the first time since the breakup of his second marriage, in 1998.
Those changes are less traumatic than the existential threats to print media in an era of free online content. Even though Playboy was the first magazine to establish an Internet presence, the publication has suffered from an industrywide fall in circulation. "I thought it was the future," Hefner says of the company's early steps online, but blames "the business end of our business" for ignoring the potential and falling behind. He fully expects to survive.
Leading the magazine for him in Chicago is editorial director Jimmy Jellinek, who came to Playboy after a decade of gigs as editor of the exploding Maxim, FHM, Stuff and Complex, the kinds of next-gen young men's magazines once expected to eclipse Playboy. Jellinek now dismisses each of the surviving lad mags as "really just a pamphlet serving as a marketing vehicle to get Pepsi products advertising."
Jellinek grew up in the northern suburbs of Chicago, and remembers seeing the original Playboy tower above the city as he rolled along Lakeshore Drive. "It was the Playboy building, man. You're talking about one of the world's most resonant brands, you see the name, you see the bunny — it's imbued with a certain sense of values, and you immediately know what it stands for. When you saw the building, you'd get excited. We'd take our pictures out in front of the building. It was something very much part of the fabric of the city."
The editor is now an aggressive, almost defensive advocate for the historic publication, and has no patience for critics who have questioned the viability of a lifestyle magazine for virile men on the prowl when its symbol is a wrinkled man in his 80s.
"I don't see any prevailing wisdom from anybody else in the magazine world," Jellinek says. "All these analysts have never worked on a magazine. ... These guys just sit and throw rocks without any basis for conversation whatsoever."
He meets with Hef on occasional trips to Los Angeles, but "the bulk of our relationship is on the phone and is through memos." They agree on the ongoing direction of the magazine, changing little from its heyday, still drawing attention for the monthly Playboy Interview. (Rocker John Mayer got in as much trouble this year for his racial/sexual wisecracks as Jimmy Carter did while a presidential candidate, with his 1976 admission to "lust" in his heart.) There is high-end fiction, pop culture and investigative journalism in the classic mode, beneath the notable bylines of Martin Amis, Bill Zehme, Stephen King, Paul Theroux, John Waters and Roger Ebert, even if the general magazine audience has forgotten it's still there amid the nude women.
"Success and popularity by their nature are like a bell-shaped curve. You have the high point and then there's an aging process, etc. The remarkable thing in terms of Playboy — certainly in terms of my own personal life — is how this thing has gone on and on," Hef says. "We sell fewer magazines in the old-fashioned way than we did in the '70s and '80s, but we reach a larger audience now on a global level than any other time in history. ... I must be doing something right."
Hefner does not deny the economic problems facing his magazine. "That's real. We live in the real world. But it's more interesting and newsworthy when it's related to Playboy. We're doing better than some, and not as well as others."
It is the running theme of recent news coverage of the Playboy empire, with serious implications for Hefner's future. After two decades as CEO, his daughter, Christie Hefner, stepped down, and new corporate leadership began to make changes, cutting costs through layoffs and consolidation. "It wasn't just business as usual," Hefner says now of the move. "We had to do some dramatic things."
More alarming was discussion of a sale, and the possibility of real changes in Hef's rigid schedule, with outsiders suggesting the Playboy Mansion be sold, his legacy dismantled, as if the central figure throughout Playboy's history were as interchangeable as the CEO of General Mills.
Then came Hefner's surprise July 12 announcement of his interest in taking Playboy Enterprises private, offering to buy out minority shareholders for $5.50 a share (for a total of $123 million), which represents a 30 percent leap over the stock's most recent closing price. Within days, a lawsuit was filed in Delaware State Court against Hefner and members of Playboy's board of directors by a group of irritated investors, who had watched with horror as stock value plummeted. The share price was at $15 as recently as 2006.