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.”  

* * *

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.”

* * *

Jellinek’s stylishly spare 16th-floor office in the middle of Playboy’s corporate headquarters in the Gold Coast has all of the accouterments of swag: liquor bottles, midcentury furniture, and a collectible poster for Hunter Thompson’s book Fear and Loathing in Las Vegas with a Ralph Steadman illustration. On the wall beside Jellinek’s desk is a photograph by Jim Marshall of Johnny Cash raising his middle finger while playing in San Quentin State Prison in 1969. The image fits Jellinek’s leitmotif: his take-me-as-I-am-and-if-you-don’t-like-it-then-screw-you attitude. “What you see is what you get with me,” he tells me. “I don’t try to hide my personality.”

Jellinek’s boyish face is covered by a few days’ stubble. His wavy brown hair is jelled in place. Dressed in a brown blazer, jeans, and white Adidas sneakers, he wears his hip uniform well while holding onto a certain rumpled quality. By various accounts of wild-and-crazy escapades, he owns a high-wattage personality, though during our interviews he remains mellow, if not dead serious—perhaps because of the Playboy publicist in the room, keeping an eye on him. 

Stories abound about Jellinek’s prolonged adolescence. He likes to play loud music in his office and walk around barefoot, say staffers. At one recent Playboy party held at the old Gold Star Sardine Bar, Jellinek was so drunk that he fell out of a shopping cart appropriated from a grocery store next door. “It’s actually impossible to humiliate him, and that gives him an amazing strength,” says Randall.

Still, Jellinek insists that editing Playboy has a maturing effect (so, too, perhaps, does being a married father of two). Behind his desk, a bookshelf teems with leather-bound volumes of every issue of Playboy ever published—his “bible,” as he puts it—a daily reminder of the heavy load he’s shouldering: “If you think about the legacy, it’s a tremendous burden.”

Sipping on a Playboy-brand energy drink, Jellinek talks in near-evangelical tones about the company—the brand, the magazine, Hefner, and the rest of the people who work there—which makes me wonder at times if his drink isn’t spiked with corporate Kool-Aid. In any case, it’s obvious that he cares deeply about the success of the magazine, and he’s a great salesman for it. When he talks about Playboy’s rosy future, he actually sounds convincing, even when he punctuates his sentences with “man,” “dude,” and “bro.”  

“Aren’t you at all worried about Playboy’s survival?” I ask.

“Not in the slightest. Dude, you’re talking about the world’s strongest brand—something that’s as recognizable as the Golden Arches and the Nike swoosh. You’ll see more magazines die off. Playboy won’t be one of them.” 

* * *

Jellinek honed that confidence—or at least the semblance of it—growing up in Highland Park. His father, John, was a venture capitalist who raced cars and owned a Ferrari. His mother, Jane, owned a bookstore in the Hubbard Woods district of Winnetka. His was a “Newsweek house,” he says, but Jellinek would steal copies of Playboy from a friend’s dad and stash them in his Hot Wheels carrying case. He insists that even at a young age he didn’t just ogle the nude pictorials; he read the magazine for the articles. “It was like this weird, sophisticated adult world,” he says. “I didn’t quite understand what it was about, but I knew it was something cool.”

His friends say young Jimmy had a knack for cool. “He was into David Letterman before any of us,” recalls Evan Rogers, one of Jellinek’s longtime friends. “And then he’d wear the khaki pants and gym shoes, which was, like, Letterman’s signature back in the day.”

Jellinek was also fascinated by rebellious youth culture. He read Rolling Stone cover to cover and devoured books by the Beat generation and counterculture writers. (He used to drive a Jeep with the vanity plate “furthr,” echoing the one on the rainbow-painted bus driven by Ken Kesey and the Merry Pranksters.) “Even back then, everything I did and thought about and read and consumed was in sort of preparation for this day,” he says.

And just like the original gonzo journalist Hunter Thompson, Jellinek was guilty of some mischief himself. “My mother found out from another mom at the deli counter at Sunset Foods after my sophomore Model United Nations trip that I lost my virginity,” he recalls with a laugh.

After graduating from Colorado College, Jellinek worked at the men’s magazine Details, then moved to Heavy.com, a website popular for its humorous videos. Starring in his own series of webcasts, The Jimmy Show, Jellinek crisscrossed the country for on-camera interviews with a confederacy of oddballs, including a man who sold his own urine on the Internet and the inventor of fart-proof underwear. Jellinek’s footage during Woodstock 1999 became something of a web phenomenon. Sporting hair dyed bright orange, Jellinek joined in the debauchery, urinating on a police car and rioting with concertgoers. Recalls David Carson, Heavy.com’s cofounder: “We would sometimes get a little scared when he was going out that something serious might happen—that he might hurt himself or we might have to bail him out of jail for something he did.” 

Around this time the lad mags burst onto the scene—Maxim, Stuff, FHM, and others—American versions of the bawdy British glossies that quickly surpassed the readership of traditional men’s publications such as Esquire and GQ. The laddie editors and executives became minor celebrities—regulars on the party circuit and staples for the gossip columns. “These magazines at the time were so successful, and the success of them could be felt with such immediacy,” says A. J. Baime, another Maxim transplant, who has been at Playboy since August 2003.

Playboy tried to steal a little lad-mag thunder in 2002 by hiring James Kaminsky, Maxim’s executive editor, and moving its editorial offices to New York. (Kaminsky left after a rocky year-and-a-half tenure in which his new editorial direction—some would call it “dumbing down”—didn’t jibe with readers and advertisers and his management style ruffled feathers.)

Jellinek joined the lad-mag party in 1999 by signing on with FHM. As a writer-at-large, he covered pop culture and products, along with hair-raising true crime. Eventually, he moved through several magazines in the stable of Dennis Publishing, the publishing frat house built by the lad-mag pioneer Felix Dennis. “Dennis Publishing was run like a British boarding school,” says Jellinek. “It was a free-for-all in there. But as much fun and as much of a party as it is—that’s part of the trickery. It takes a lot of hard work to make something very stupid.” 

But by the mid-2000s, the lad-mag kegger was winding down, and the magazines were fading out faster than Amy Winehouse. Hired in May 2006 to run Dennis’s crown jewel, Maxim, Jellinek was fired in August 2007 after the company sold the American versions of its magazines to the Alpha Media Group. The new publisher wanted to install his own team. “This will probably be my last job in publishing,” Jellinek told the New York Post after being axed. “The print ride has ended for me.”

Reminded now of his comments, Jellinek smiles. “You just say that shit because it sounds good at the time,” he says. In reality, he was pretty down about getting pink-slipped. “It was a very difficult summer,” he says. “It was the first time I had been fired from a job. It just dragged out and out and out. I had started reading in the gossip columns about my job being shopped around in May. It just makes you crazy.”

For the first time, really, Jellinek felt the harsh glare of the New York media limelight. “It’s so lame,” he says, remembering it all now. “It’s just a bunch of high-school newspaper geeks living out their dreams and frustrations based on where they sit on the masthead. Stepping away from it now, it’s such a relief not to be part of it.”

Jellinek returned to Heavy.com—this time in charge of all of the site’s original content and programming. He concocted a series of popular webisodes that parodied hit television shows, including “Over the Hills,” a spoof of MTV’s The Hills, with senior citizens acting out scenes from the actual show, and “Flex and the City,” featuring female bodybuilders as the cast of Sex and the City. But when Jellinek saw the opportunity on an Internet job site to return to magazines—even if it was on Playboy’s digital side—he jumped. (In August 2008 he was named senior vice president of digital content.) “Jimmy was always fascinated by print,” says David Carson. “It was like this itch that he had to scratch with being an editor at a magazine.”

* * *

After just six months as digital editor, Jellinek was at a friend’s bachelor party in Squaw Valley when Jerome Kern, then the interim CEO of Playboy Enterprises, called and said, “Hef wants to see you.” Kern told him the company was consolidating its print and digital operations and was moving the magazine’s editorial offices back to Chicago, and he offered Jellinek the editorial director’s job. Chris Napolitano, a 20-year Playboy veteran who then occupied the top chair, wanted to stay in New York. (He remains the magazine’s editor-at-large.)

“I think I was already eight beers in at that point,” recalls Jellinek, and the drunken racket of his friends was drowning out the conversation. “It was surreal. I’m on a cordless phone outside going, ‘You guys, shut the fuck up!’”

The next morning, Jellinek flew to Los Angeles to meet with Hefner for the first time. “It isn’t a done deal till you look the man in the eye and he thinks you have what it takes,” he says. Hefner was impressed. 

Jellinek’s leapfrog jump to editorial director came as a shock to most Playboy staffers. “I think a lot of people at first were like, ‘This guy?’” recalls Baime. Among other things, Playboy had already bought into the lad-mag vibe before, via James Kaminsky, with mixed results at best. Would Jellinek simply be Kaminsky 2.0?

But soon after taking the job, Jellinek read 30 years’ worth of the magazine, front-to-back, to get a fuller understanding of Playboy’s look, feel, and voice during its prime. He also exercised good retail political skills—ingratiating himself with his colleagues over drinks and conveying his approachability. He likes to say that he welcomes and encourages input and ideas from anyone, even from the lowest rungs of the company. In a taped interview for Crain’s “40 Under 40,” for instance, he states: “I’ve found that by letting ideas bubble up from the bottom, come from anywhere—I don’t care if you’re the receptionist or work in the mailroom—if you’ve got a good idea, it’s going to go in the magazine, or it’s going to go on the website.”

Sounds good, but when I ask one Playboy staffer about that assertion, he snickers and says, “I’ve never seen an idea from the bottom, ever, anywhere, and I’m talking across the company.” 

Minor griping aside, Jellinek has won over most of the close-knit staff. “People who are thrust into positions of power so quickly, like he was, tend to be disliked, whereas Jimmy’s not,” says Baime. “Let me put it this way: We have lots of fun. Lots of it.”

* * *

On my second visit with Jellinek, I sit in on one of Playboy’s weekly editorial meetings. It’s the first week of January, and some 20 editors and assistant editors are gathered in a conference room to go over the March and April issues. Looking tanned from a recent family vacation in Mexico, Jellinek sits at the head of the table and runs through the monthly lineup: Is the cologne story turned in? Is there good art for the feature opener? As he ticks through the long to-do list, one can almost see Jellinek’s tan begin to fade. “There’s a lot of shit hanging out still,” he tells the group, as if to say, “Let’s tie up the loose ends, pronto.”

Though Jellinek’s place is at the head chair, Hugh Hefner looms in the room like an elephant wearing silk pajamas. “Has Hef seen it?” “Will Hef like it?” Jellinek regularly asks the others. At one point he warns the group that “Hef is in, like, typo mode”—meaning read your copy carefully, so as not to annoy the boss.

Afterward, I ask Jellinek if he ever feels hamstrung by Hefner’s penchant for micro-managing. “Hef is the editor in chief of the magazine 8,000 percent,” he says. “Like, everything I do, I do for him. I want to hit a home run for him every single time.” 

What if you disagree with him?

“You don’t argue with Hef,” Jellinek says. “He’s the editor in chief, man, so his say is final.” 

Separately, I raise the question of what Playboy staffers call the “Hef factor” with Mr. Playboy himself. “I suppose, quite frankly, that it’s a team operation,” Hefner tells me by phone from the L.A. mansion. The magazine, he continues, “has always been a very personal book for me. I’m not looking for someone to reinvent the wheel. What I’m looking for—and what I got from Jimmy—is a fresh take on classic Playboy.” In other words, don’t count on Hefner, who turns 84 in April, to step aside anytime soon.

Arthur Kretchmer, among others, acknowledges that Hefner can be stuck in his ways but says Hef has been loosening his grip gradually over the years: “There’s a lot of ingrained habits there. Hef will give Jimmy the freedom as they go along, as he believes in him.” 

In the meantime, Jellinek has not been shy about messing with convention or sweeping away some of the magazine’s cobwebs. Marge Simpson, for example, was the first cartoon character ever to make Playboy’s cover. He all but scrapped the NFL preview coverage—shrinking it to less than a page—in favor of an oral history of the badass Oakland Raiders teams of the 1970s. He has also pushed for edgier interviews, such as the one with Seth MacFarlane, the creator of Family Guy, as well as for more graphic novelizations, including one based on Quentin Tarantino’s Inglourious Basterds.

Hefner and the corporate brass have so far liked what they have seen. “The magazine once again can say very legitimately, ‘You read it for the articles,’” says Hefner, laughing.

Last November, Scott Flanders, the CEO, promoted Jellinek to oversee all of Playboy’s ancillary entertainment businesses. In this role, Jellinek has a hand in developing shows for Playboy TV and its satellite radio station. For example, Jellinek helped drive a recent decision, along the Tiger Woods line, to nix a proposed TV reality show in which homely women from small-town America would receive Playboy-style makeovers to become Playmate material. Flanders recalls, “Jimmy immediately said, ‘Nope, we’re not doing that. Playboy is about beauty. We’re not going to associate Playboy with women that don’t meet our standards.’ Had he not been at that meeting, the result would’ve gone in a very different direction, because an idea like that—like the ‘Girls of Tiger’ idea—immediately sounds interesting.”

Some wonder, though, if Jellinek can juggle the magazine duties with his other tasks. “Editorial director is a debilitating job by itself—you have to put up with a lot of stress,” says Lee Froehlich, Playboy’s executive editor. “How’s this guy going to do two jobs? I keep thinking, like, he’s going to start crumbling under the pressure, but so far he’s been able to avoid it.” 

“I like to be challenged,” Jellinek says. “If I’m going to fail, I’d rather fail spectacularly than succeed meekly.” Then, paraphrasing a line from Top Gun, he adds, “I’m not happy unless I’m going Mach four with my hair on fire.”