Revenge of the Fox News Frat Boy

Now that Greg Gutfeld is 50, has settled in trendy Tribeca with his beautiful Russian wife and has become a famous Fox News personality who makes a handsome living while mingling with fellow celebrities like Louis C.K., will he finally shed his self-flagellating misanthropy and go mainstream-corporate?

Not likely, it appears, but to find out for sure, Fox News loyalists—and perhaps even viewers of less “fair and balanced” channels—will have to tune in to The Greg Gutfeld Show, which he calls “a news-slash-talk-slash-variety show” with “weird little pockets of absurdity” and premieres this Sunday at 10 p.m.

“I think it’s like a school night, so it’ll probably be people who are looking forward to the week and maybe need a little bit of POSITIVE ENERGY!” Gutfeld fairly shouts, half-derisively, when I ask who his target audience might be. “Is that a bullshit answer or what?”

A 5-foot-5-inch caffeinated dervish—Gutfeld makes incessant “short” jokes about himself, beating any aspiring hecklers to the punch line—he has just torn off his necktie in the green room and hoisted his backpack to head out the door. He mutters a mild complaint when the network publicist informs him that he must hurry to participate in yet another Gutfeld Show-themed interview on the PR schedule.

He has just finished co-hosting an installment of The Five, the raucous 5 p.m. political and pop-cultural panel program that Fox News Chairman Roger Ailes invented in October 2011 to fill the vacancy created by the abrupt departure of Glenn Beck.

As usual, Gutfeld has played court jester on this particular episode, mercilessly teasing his fellow panelist Kimberly Guilfoyle during a four-minute video segment shilling her new memoir and self-help book, Making the Case.

“You were a model, too!” he chirps self-mockingly at the appearance of a photo of a much younger Guilfoyle rocking a leopard-print jumpsuit years before her crime-fighting career as an assistant district attorney; he’s narrating the images on a studio monitor in a running off-the-air commentary that viewers can’t hear. “First marriage!” he announces when a photo flashes of Guilfoyle and Gavin Newsom, then her husband and San Francisco mayor, now California lieutenant governor. And when a clip runs of the twice-divorced Guilfoyle being smooched by New York Jets legend Joe Namath, Gutfeld bellows: “Look at him, that dirty old man!”

Obviously used to it, Guilfoyle laughs stoically. On the air, Gutfeld ostentatiously pages through her book, looks up, and declares in mock-irritation: “We lived together in Texas for four years and you act like it never happened!” A few minutes later, while holding up Guilfoyle’s book sideways: “The pictures are amazing!”

Gutfeld’s bratty performance would be familiar to fans of Red Eye, the 3 a.m. Eastern Time weeknight show he hosted for eight years and 1,853 episodes until his leave-taking three months ago to focus on the next big thing.

“The crux of my audience was people with overactive bladders, breast-feeders, and meth addicts,” he says of the insomniac-friendly Red Eye, which under Gutfeld’s reign trafficked in political incorrectness, a brand of humor slightly earthier and sillier than, say, Dorothy Parker’s and Robert Benchley’s bons mots at the Algonquin Roundtable, and featured, more often than not, a leggy, short-skirted female guest-panelist seated closest to the camera. (A new permanent Red Eye host has yet to be named.)

“During the week, you’re on a roll, writing and writing and writing,” Gutfeld tells me, describing the feverish rhythm of a workweek in which he not only will helm his eponymous Sunday show but also continue co-hosting The Five and doing a regular monologue on The O’Reilly Factor. “At the end of the week you have a summary of what you’ve been doing and thinking about, and so you smush it around and turn into something else. There are things I didn’t say on The Five that I should have said and that might contribute to the new show. I guess it’s about repurposing and saving stuff like that. Plus, I’ll have help, you know.”

While admitting to feeling a tad “panicked” when Ailes gave the green light to the new program—an idea they’d been kicking around for months—Gutfeld says he could never see himself doing just one thing, a la John Oliver’s laser-like focus on HBO’s Last Week Tonight, the critically acclaimed half-hour featuring what might be called investigative satire.

“The thought of that drives me crazy,” says Gutfeld, who expresses admiration for Oliver’s show. “I’ve done two shows every day for years, but I don’t think I could work on just one show a week. I would go crazy and I would drive everybody nuts. I’ve got to feel like I’m under pressure.”

As a practitioner of comedy and satire himself, Gutfeld speaks with a degree of respect for departing Daily Show host Jon Stewart—a constant critic and lampooner of Fox News but “an incredibly talented comedian”—and even Stewart’s designated successor, Trevor Noah, although he finds their politically liberal perspectives predictable. “I don’t think Trevor Noah got his job by being a conservative,” Gutfeld says.

“I always thought Jon Stewart was an extremely good surgeon with his scalpel,” Gutfeld says. “He would have Republicans on who I guess were unclear about what Stewart was up to, and while Jon Stewart was being nice, he was building a case for drowning them. And the Republican would think, ‘This isn’t going so bad,’ and then Stewart opens up the Republican’s book and says, ‘On Page 43 you say this. You can’t be serious.’ And then the person is caught.”

Gutfeld also describes himself as an ardent fan of the subversive, anti-showbiz, anti-celebrity, pre-CBS David Letterman, especially the 1980 morning show on NBC, but eventually stopped watching as he perceived his one-time comedy idol becoming bored—and boring—with a late-night talk show that became part and parcel of the showbiz establishment.

The day after Letterman’s celebrity-studded swan song last week that ended a 33-year career on late-night television, Gutfeld recalls thinking that it was “basically a parade of famous names before an open casket.”

Likewise, Gutfeld—a punk rock fan as a teenager who still likes to write about music on his Gut Check blog—used to voraciously and pleasurably consume Rolling Stone magazine. But no longer, he says, not since publisher Jann Wenner turned it into a vehicle for his political and social agendas. The bogus University of Virginia rape story is just one symptom of the magazine’s decline, Gutfeld argues.

“I hate Rolling Stone—because I loved it so much,” he says. “I had the ‘Cheap Tricks’ cover and the Clash cover on my wall for years, and I just hate what happened to it. It just became the smarmy grad student that sits next to you on the bus.”

Gutfeld joined Fox News in 2007 after a checkered career writing for and editing magazines such as Rodale Press’s Prevention and Men’s Health, and two of the late Felix Dennis’s lad mags, Stuff and Maxim U.K. The pattern of Gutfeld’s employment history is both impressive and depressing: He’d climb the greasy pole and reach the pinnacle—becoming editor in chief of Men’s Health, Stuff, and the British Maxim—only to be fired and sent tumbling to the ground.

His loss of the top job at Stuff in April 2003, after hiring three dwarves through a casting agency to disrupt an American Society of Magazine Editors seminar on “What Gives a Magazine Buzz,” was spectacular enough to prompt a long profile in The New York Times.

The “little people,” as Gutfeld today calls the dwarf-actors—“because I’m not much taller,” he claims—were ejected from the seminar for chomping noisily on fistfuls of potato chips and engaging in earsplitting conversations after letting their cellphones ring and ring. In the Times piece, Gutfeld made pained jokes about his lack of success with women and came across as a bit of wacko, adopting “the persona of a seedy, hard-drinking gadfly,” according to the story, and once wearing “a bear-skin rug—complete with the taxidermic teeth and tongue—to a fashion show.”

Months later, Gutfeld had just become editor in chief of Maxim U.K. when he attended a conference in Portugal of editors of all 30-odd Maxim titles around the world. Staying in the adjacent hotel room was Elena Moussa, a 5-foot-10 “gorgeous former runway model-turned-photo editor of Maxim Russia,” as she was later described in the New York Post’s Page Six column.

“I actually met her my first day on the job,” Gutfeld says. “When I saw her, I said to the editor of Maxim Russia, ‘Who is this woman?’ And I foolishly hit on her for three days. She was pretty cold to me, and finally I asked her out on a date.” Apparently, sparks flew. “And then she moved to London to be with me.” They celebrated their 10th wedding anniversary last December.

A former liberal who switched to conservatism after getting annoyed with the sanctimony and hypocrisy of his fellow lefties at the University of California at Berkeley and then switched to libertarianism after getting annoyed with the sanctimony and hypocrisy of his fellow right-wingers, Gutfeld these days calls himself a “conservatarian.” Gung-ho on patriotism and national defense but laissez-faire on social issues, he’s proudly irreligious and favors the decriminalization of prostitution and illegal controlled substances.

“Everybody has their own right to seek their own oblivion,” he says. “This world is painful.”