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Playboy editorial director Jimmy Jellinek’s hop to the top

Hare Tonic: After just over a year as editorial director, 35-year-old Jimmy Jellinek has injected new life and energy into Playboy (the Marge Simpson cover was his brainchild). But can anyone—even a brash former star of the lad-mag genre—rescue this listing flagship?

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Jimmy Jellinek, editorial director of Playboy magazine
Jellinek (left) says his mission is “to creatively channel the genius of Hugh Hefner” while trying to make Playboy relevant to a new generation.


In the media melee following the Tiger Woods bimbo eruption, Scott Flanders, the chief executive of Playboy Enterprises, figured that the scandal had Playboy potential written all over it. He could already picture the spread: “The Girls of Tiger,” or something like that. As Flanders recalls, “My instincts were, Let’s jump on this—the dogs want more dog food. Let’s give it to them.”

But when Flanders broached the idea to Jimmy Jellinek, the magazine’s recently installed editorial director, Jellinek was unconvinced. The idea had crossed his mind, too, but, says Flanders, “Jimmy, from the very beginning, said this isn’t a story that our audience is happy about, because it’s about betrayal; it’s about integrity. He said, ‘No one is celebrating this—women aren’t happy about it, and men aren’t happy about it, and Playboy is all about bringing enjoyment.’”

Not so long ago, Jellinek would have been trying to sign up Tiger’s conquests faster than Woods can swing a driver. A former “magazine outlaw,” as one of his colleagues describes him, Jellinek gained notoriety as the editor of raunchy publications with a frat-boy superficiality and an eagerness to pull off practically any stunt to garner buzz and ballyhoo.

But this is Playboy. And Jellinek now serves as guardian of the Bunny, a weighty, if sinking, icon in the magazine world. In his mind, Playboy venerates sophisticated sexuality, not sleaze. “I like to say we’re a sexy version of The New Yorker or Vanity Fair more than anything,” says Jellinek, without breaking a smile. “We are a magazine of ideas; we want people who want to think and contemplate and have a magazine that challenges them.”  

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Jimmy Jellinek’s shot to the top of the men’s magazine world has been fast and wild, like an uninterrupted Red Bull-and-vodka bender. Schooled in the racy Fleet Street ways of the so-called lad mags, by the age of 30, Jellinek was the top editor of the category’s second-biggest title, Stuff, and by 31, he was editing the biggest: Maxim, which at its peak counted 14 million readers.

Now 35, the enfant terrible emeritus is only the fifth person in Playboy’s 56-year history to hold the position of editorial director. In November 2009, after not even a year at the top of Playboy’s masthead, Jellinek climbed another rung on the corporate ladder; he was named chief content officer—meaning he directs the creative development for all of Playboy Enterprises’ media properties, including print, online, mobile, television, film, and radio.

But is the company ladder in Playboy’s case actually a steep chute?

Six hundred and seventy-three issues after Playboy’s debut in 1953, the magazine—as well as its parent company—is fighting for survival in today’s shifting media landscape, struggling to stay relevant in the crowded marketplace. Playboy lost $8 million last year. As at many magazines, ad pages have plummeted, in Playboy’s case down 33 percent in 2009 compared with the previous year. In January 2009, six years after moving its editorial operations to Manhattan from its original home in Chicago, the magazine pulled up stakes on Fifth Avenue and returned to its corporate headquarters on Lake Shore Drive. (A Playboy spokeswoman denied a rumor reported recently in the New York Post gossip column, Page Six, that the company is considering moving the magazine’s editorial offices to Los Angeles as a cost-saving measure.) In October, Playboy decided to drop its rate base (the circulation promised to advertisers) from 2.6 million to 1.5 million, a far cry from the circulation of nearly 7 million it had during its heyday in the early 1970s. It also reduced its frequency from 12 issues a year to 11 by combining its January and February issues. More recently, the magazine outsourced all of its key business functions—advertising sales, circulation, marketing, and production—to American Media, Inc., the publisher of Men’s Fitness and the National Enquirer, among others.

The stock price of Playboy Enterprises has dropped nearly 80 percent over the past ten years. By the time Christie Hefner, who ran her father’s business for 20 years, stepped down as chairman and chief executive officer last January, the company was $156 million in the red. Through the first three quarters of 2009, the company reported net losses of $23.5 million.

At 83, Hugh Hefner has put his Playboy empire on the shopping block, albeit reluctantly, but the company has struggled to find a buyer. One of the most promising reported suitors, the Iconix Brand Group, which owns and licenses well-known brands like London Fog and Joe Boxer, broke off talks with Playboy in December, by some accounts because of complications over Hefner’s role under new ownership. No other buyers have since come forward, at least not publicly.

Of course, Jellinek isn’t expected to solve all of the company’s woes. But he is under great pressure to reinvigorate the flagship magazine, still the primary driver of the overall Playboy brand. “My job is to creatively channel the genius of Hugh Hefner into the magazine and make it an outstanding product that people want to buy, and that’s what I focus on day to day,” says Jellinek. “If I start thinking about all of the other things on top of that—that becomes a crushing load, and that’s a load I can’t carry.”

Only eight issues have carried his editorial stamp so far, but several current and former staffers say that Jellinek has already injected the magazine with a burst of creative energy. For example, when a PR person for The Simpsons called to ask about a possible tie-in with Playboy as part of the show’s 20th anniversary season—maybe a pinup featuring Marge—Jellinek took the idea to a new level: “You think we can get them to do the cover?” he asked the deputy editor, Stephen Randall.

Last November’s cover featuring Marge Simpson, posed naked, peekaboo-style, behind a Playboy Bunny chair, set off a chorus of chatter. “That was all Jimmy,” says Randall.

Arthur Kretchmer, who retired in 2002 after a 30-year run as Playboy’s editorial director, says it’s too soon to judge Jellinek’s stewardship, but Kretchmer—a tough critic, by all accounts—is impressed so far by Jellinek’s vision and charmed by his chutzpah. “This is a raw force, this kid,” says Kretchmer. “I think Jimmy is right for the time. His energy and his daring—that’s what the times need.” 

Other media observers question whether any amount of tuning will be enough to reconnect Playboy with today’s younger readers, who are saturated with media choices and who generally think of Playboy as Dad’s magazine. “I hate to say [it], but this one’s impossible,” says Samir Husni, a journalism professor at the University of Mississippi who follows the magazine industry. “The country has changed, the mentality has changed, and a lot of the newer audiences who are buying magazines did not grow up on Playboy.”  

The marketplace aside, Playboy’s biggest obstacle, in Husni’s opinion, is its maverick founder Hugh Hefner, who refuses to relinquish the reins. While Jellinek may run the magazine on a day-to-day basis, Hefner is editor in chief, and not just in title. From the Playboy mansion in Los Angeles, he still works full days on the magazine, and, in fact, he’s something of a control freak: He approves every Playmate, every cover, every photo, every story, every layout, and every cartoon that goes in each issue.

The problem, say critics, is that Hefner’s taste—his sense of what’s cool—is now anachronistic. (The cartoons haven’t changed since the Rat Pack era.) And inside Playboy’s pages, he remains front and center. “When you look at the magazine trying to reach this younger generation, and you open up to page seven or page eight and see Grandpa surrounded by three semi-naked women, I mean, does that really excite young people?” asks Husni.

New York magazine has already written Playboy off for dead, recently including it in its catalog of “artifacts” of the aughts—as obsolete as lickable stamps and cassette tapes.

As it turns out, Jellinek thinks that the best path forward for Playboy—the surest way to regain its relevancy in the marketplace—is to go backward and try to recapture the old-fashioned sexiness and seriousness of the magazine’s glory days. “We’re trying to create a more analog, old-school experience,” he says. He points to the resurgence of interest in vinyl record albums as an example of what he has in mind. “What we’re trying to do is create the excitement and surprise of the sixties and seventies. When Playboy used to come in the mail, there were lightning bolts coming out of it. You knew when you picked up this magazine you’d be reading the coolest fiction; you’d be reading the coolest articles; you would be 100 percent informed. That’s what I want to do with this.”

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