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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.”
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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.”
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