One evening in May, the most-watched man in late-night television these days staked out a curious if characteristic position: A 38-year-old teacher who allegedly had sex with a 16-year-old student, the host said, was the hero this nation needed.

“Can we live in the real world?” asked the host, Greg Gutfeld of Fox News, before invoking the Van Halen song “Hot for Teacher.” “It wasn’t written about ‘Hey, let’s have a responsible relationship with someone close to my age.’”

Reaction on the set of his show, “Gutfeld!” — where a regular, Kat Timpf, declared herself “vehemently against banging kids” — was mixed. The judgments online were swift.

“Fox News Is Now Praising Statutory Rape on Air,” The New Republic wrote, one of nearly a dozen outlets to sternly relay Mr. Gutfeld’s doings on his political satire-ish 11 p.m. hour.

In Mr. Gutfeld’s telling, his teacher bit and the reaction it spawned are part of the grand plan that has delivered him to the ratings summit of late night, to the surprise and occasional horror of many former colleagues and industry stalwarts. To their eye, he has completed a baffling march from Fox’s 3 a.m. slot to a nightly forum where consciously hacky jokes about women drivers and Hunter Biden’s addictions garner a larger audience than “The Tonight Show.”

But the left’s timid and often self-serious vision of late night, Mr. Gutfeld suggested, is precisely why few saw him coming — and why some assumed the teacher rant was sincere.

“Recreational beliefs,” he said during a 90-minute interview, describing the entertainment value of defending the indefensible, within reason — whether or not he believed what he was saying, whether or not his audience of nearly two million believed that he believed it.

“They don’t work when you’re talking about, like, 9/11 or Sandy Hook. Those are not recreational beliefs,” he added. “Recreational beliefs are things that don’t hurt anybody, and they spark a conversation.”

He smiled.

“Taken out of context,” he added, “you can believe that I’m nuts.”

Questions of intention and audience fluency — of what viewers are meant to understand about what is uttered on Fox’s air — have shadowed the network’s volatile and damaging recent history, suffusing its gargantuan Dominion settlement over bogus election fraud claims and the attendant departure of Tucker Carlson, its most popular anchor.

Yet as Fox plots its next chapter, executives have placed their non-recreational belief in Mr. Gutfeld, elevating his merry trolling and just-kidding-not-really-but-maybe bearing as an institutional voice for the next generation of viewers.

As part of a lineup shuffle hastened by Mr. Carlson’s ouster in April, Mr. Gutfeld, 58, will move to 10 p.m. later this year, a promotion befitting his escalating clout at the network. The changes announced by Fox this week were the network’s first major overhaul of prime time programming since 2017. Jesse Watters will take over Mr. Carlson’s 8 p.m. slot, and both Mr. Gutfeld and Mr. Watters will remain co-hosts of “The Five” at 5 p.m., the most-watched show in cable news.

Though far less dissected than Emmy-nominated counterparts like Jimmy Fallon and Jimmy Kimmel, Mr. Gutfeld reliably outrates their Trump-dinging monologues and celebrity-guest banter with scatological digressions, cameos from a low-rent presidential impersonator and a booking roster that can count Larry Kudlow as the get of the night.

“We talk about Greg’s bowels way too much,” said T.W. Shannon, a “Gutfeld!” guest and former Republican legislator in Oklahoma. “There’s an audience for that, too, though.”

For a network long mocked for its geriatric demographics, Mr. Gutfeld has helped attract (relatively) younger fans: Among those 25 to 54, “The Five” and “Gutfeld!” regularly rank as two of the highest-rated hours in cable news.

Last year, Mr. Gutfeld repeatedly eclipsed Stephen Colbert, long the most-watched late-night host.

While Mr. Colbert has consistently reclaimed the top spot, the Hollywood writers’ strike has functionally left Mr. Gutfeld and his non-guild team as the only game in town, producing a modest audience bump, according to Fox. “And I am for no choices,” he joked recently.

After decades of cultural dominance by left-leaning late night — whose hosts ridiculed George W. Bush, riffed with Barack Obama and recoiled at Donald J. Trump — Mr. Gutfeld’s striking inversion is a hard-won victory for the right.

Like “The Daily Show” with Jon Stewart at its Bush-era peak, Mr. Gutfeld has created a waggish refuge for viewers aghast at the country’s political direction.

Unlike Mr. Stewart, Mr. Gutfeld has never done standup, does not call himself a comedian and spent much of his early career publishing paeans to male obnoxiousness in men’s magazines.

“It takes a healthy dose of arrogance to be a winner,” Mr. Gutfeld wrote in Men’s Health’s in 1995. The headline: “Be a jerk.”

He has faithfully followed his own advice. The cover of an upcoming essay collection shows an implausibly sinewy Mr. Gutfeld towering above his peers beneath the title “The King of Late Night.”

The label has not pierced every information bubble.

“I seriously need to sit down,” the comedian Amy Schumer said when told of Mr. Gutfeld’s lofty ratings perch, fondly recalling her guest spots years back on his considerably-less-watched Fox overnight show, “Red Eye.”

“He was a nice guy,” she added. “He just happens to be a part of this corporation that has utilized social media to end democracy.”

Mr. Gutfeld’s success speaks in part to the fragmentation of this television age, when the nightly winner draws a small fraction of the audience that Johnny Carson once commanded. There are also some statistical caveats: “Gutfeld!” has aired more than 30 minutes earlier than some competitors on the East Coast — and at 8 p.m. out West.

At a minimum, Mr. Gutfeld has positioned himself as perhaps the fullest realization of what today’s Fox is and what tomorrow’s might be, fusing a roguish contrarianism and an instinct for self-promotion with a political media ecosystem constructed to reward both.

For years, he has curated an image as a punk-loving California expat equally liable to make a bladder joke about “trickle-down economics” at the Ronald Reagan Presidential Library and an on-air joke about Fox’s recent turbulence.

“Well, thank God there’s no turmoil here,” he said dryly during a segment on upheaval at CNN. “Keep that in.”

But Mr. Gutfeld broadly validates the median Fox viewer on the issues that resonate most, including the fate of Mr. Trump, whom Mr. Gutfeld criticized sharply in 2016 before a well-timed recalibration.

He has accused others in late night of failing to adjust as he has and submitting instead to what he sees as an epidemic of left-wing humorlessness.

“It was like Trump was such an existential evil that even joking about it is unseemly,” Mr. Gutfeld said, seated inside his ample Soho apartment (previously occupied by Lindsay Lohan) with a vape pen between his fingers and a large painting of himself in plain view. “I was very anti-Trump up until when he won, and then I had to realize, ‘OK, do I continue as a broken person?’ Because he legitimately was breaking people. Because once the thing that you hate wins, what do you do?”

What Mr. Gutfeld did, in part, was capitalize on a defining talent that he and the former president share: a kind of insult conservatism that can frame any serious argument as a joke and any joke as a serious argument, leaving viewers to suss out the distinction.

“There’s sort of a nihilism at the core of that,” said Nick Marx, a Colorado State University professor and co-author of “That’s Not Funny,” a book about right-leaning comedy. He suggested that Mr. Gutfeld’s shtick was the troubling culmination of Fox’s commingling of news and entertainment.

The host’s swerves can come quickly.

Hours after Mr. Trump’s federal indictment was unsealed last month, Mr. Gutfeld sounded initially earnest about the ostensible hypocrisy of Democrats. “I’m not that interested in locking up Hunter or Joe Biden,” he said on “The Five.” “But the other side would lock up every one of us if they could.”

Something shifted in his voice.

“So, let’s go,” he said. “Let’s put ’em behind bars.”

Some co-panelists smirked.

“All of them! Every Biden! Doctor Jill!”

Now he was jabbing his finger at the air, faux-furious, swelling with recreational belief.

“How long has she been practicing on patients,” he demanded, “telling them that she’s an actual doctor?”

Mr. Gutfeld always stood out some in eastern Pennsylvania: the metal briefcase, the coastal sarcasm, the weakness for physical comedy.

“You know when someone is walking behind a couch and they can crouch down so it looks like they’re going downstairs?” said Peter Moore, a former colleague at Men’s Health, which had its headquarters in Emmaus, Pa. “Yeah, Greg would do that.”

But it was the impeachment of President Bill Clinton that especially set Mr. Gutfeld apart. “I just assumed that every editor I met would be a Democrat,” Mr. Moore said. “And I can still remember the day when Greg triumphantly walked into my office and said, ‘Well, they finally got that bastard.’”

Mr. Gutfeld’s political journey began, like those of many right-leaning thinkers in the Trump years, while surrounded by California liberals.

At his Catholic all-boys high school in San Mateo — where, he has said, his schoolmate Barry Bonds, the future slugger, cheated off him in Spanish class — Mr. Gutfeld recalled receiving extra credit for campaigning for the nuclear freeze.

At the University of California, Berkeley, he was a Sigma Chi fraternity brother and has never forgotten being heckled by protesters he believed to be from “Take Back the Night.”

“I mean, walking home from the library and getting yelled at,” he said, likening the feeling to encountering Black Lives Matter demonstrators decades later in Manhattan. “That always bothered me.”

While much of Mr. Gutfeld’s success today owes to Fox’s plug-and-play capacity to mint stars, his arc as a cultural and political taste-shaper doubles as a jaunt through the last three decades of American media — with space at the top for a pinot-drinker who hates “The View,” laughing loudly at his own jokes.

After working as an assistant at the conservative American Spectator, Mr. Gutfeld wrote for Prevention magazine before spending several years at Men’s Health, in time for the swaggering prime of men’s magazines.

He unfurled grabby hooks (“Remember syphilis?”) and abundant 1990s references (“Bar foods contain more grease than Alanis Morissette’s hairbrush”).

He turned out first-person pieces on internet pornography and a nudist singles resort in Jamaica, where Mr. Gutfeld took an anthropologist to observe mating rituals.

“He was extremely curious, and he was very gentlemanly,” the anthropologist, Helen Fisher, recalled. “Certainly didn’t try to pick me up.”

Mr. Gutfeld’s elevation to Men’s Health editor in 1999, at age 35, did not imbue him with newfound gravitas. He was known to groan through story discussions, lying in gastrointestinal distress across a conference table after consuming an oversize egg salad sandwich. (Mr. Gutfeld said he approached his nightly discussions on “Gutfeld!” as “basically running an editorial meeting.”)

At a conference in Spain once — with Ardath Rodale, the septuagenarian chief executive of the magazine’s publishing company, looking on — Mr. Gutfeld delivered a presentation on go-to service-journalism subjects: your diet, your career, your waistline, your mental health.

“And then of course he had ‘your penis,’” said Bill Stump, another colleague. “I just remember Ardie saying, ‘I don’t know why he has to use that word.’”

Mrs. Rodale’s daughter Maria, then an executive at the company, recalled Mr. Gutfeld as “deeply misogynistic,” if often consistent with his laddish surroundings. She was especially troubled by his casual disparagement of Prevention (another Rodale title at the time) and its readers, whom Mr. Gutfeld once described as “lonely women with cats and psoriasis.”

“He’s small,” Ms. Rodale said, tweaking Mr. Gutfeld’s height. “He spent a lot of time bulking himself up. I didn’t hold that against him — I was at the gym, too — but I think some people come from a place of a chip on their shoulder.”

(“Making a crass joke is nothing compared to running what was once a tremendous company into the ground,” Mr. Gutfeld said in response to Ms. Rodale’s assessment. As chief executive of her family business, Ms. Rodale oversaw the sale of Rodale Inc. to Hearst for under $225 million in 2018, according to The Wall Street Journal. The company’s flagship titles — Prevention, Men’s Health — continue to publish.)

On Mr. Gutfeld’s watch, the magazine edged perceptibly into the culture wars, insulting Girl Scouts, mocking Hillary Clinton’s ankles and ranking “the best and worst colleges for men.”

“I don’t think anybody used the phrase ‘own the libs’ at that point,” said Tom McGrath, a former Men’s Health editor, “but I think it was that.”

Mr. Gutfeld was fired as editor after less than a year. His subsequent magazine career, at Stuff and later Maxim UK, followed a similar template of dicey flourishes and abbreviated tenures.

Notable features included “Ask Greg’s Mom,” which chronicled his mother’s critiques of his work (transmitted via answering-machine message), and “Fresh Off the Boat,” which offered readers the chance to meet attractive female asylum-seekers.

His most infamous stunt came in 2003 when the American Society of Magazine Editors hosted a seminar on how to generate “buzz.” Mr. Gutfeld, who loathed such self-congratulatory sessions, had an idea.

He dialed a casting agent, hired three dwarfs and dispatched them to the conference with cellphones and bags of chips. As panelists held forth on how to command attention, Mr. Gutfeld’s small contractors entered in succession, producing a symphony of chip-chomping and phone-talking that befuddled the room and hijacked the summit.

“The small-person potato-chip-eating incident,” Mr. Moore, the Men’s Health colleague, recalled tactfully.

Mr. Gutfeld had his buzz.

Mr. Gutfeld once summarized his approach to employment with some mindfully reckless counsel.

“Work with the belief that you should be fired,” he advised in 2014. “Got me to Fox.”

This was true enough. Mr. Gutfeld has said he initially connected with network executives through his friendship with Andrew Breitbart, a fellow Californian and an early contributor to The Huffington Post. Mr. Gutfeld had been writing there as he moved beyond magazines, embracing the rollicking venom of the nascent blogosphere and tormenting the in-house liberals.

“He was using a lot of all-caps,” Arianna Huffington recalled, mostly warmly.

Since his Men’s Health days, when he did occasional Fox guest spots to recommend hangover cures or the like, Mr. Gutfeld had hoped to work at the network, he said.

What he did not know was that Fox was looking for someone like him — or at least someone unusual enough to advance an unusual new venture: proving that the right knew how to laugh.

The result, somehow, was “Red Eye,” a concept that Fox brass at the time compared to making a sandwich late at night from refrigerator leftovers. Mr. Gutfeld has preferred a film analogy.

“In every situation there’s that polarity where the Republicans are Dean Wormer in ‘Animal House,’” Mr. Gutfeld said, naming the film’s antagonist. And Democrats, he continued, came off as “the fun, Jon Stewart, ‘let’s have a great time and make fun of Dean Wormer.’ And I said that my goal was to flip that.”

If nothing else, “Red Eye” would be ostentatiously weird, airing alternately at 2 or 3 a.m. Tuesdays through Saturdays beginning in 2007 and proceeding as if the team suspected that no one was watching.

Guests included up-and-coming comics, filter-averse political gabbers and the Vice co-founder Gavin McInnes, now better known as the founder of the Proud Boys.

“It was just a wild late-night show,” said Ms. Schumer, recalling her stints in the “leg chair” designated for eye-catching female panelists. “I felt appreciated there.” (She eventually stopped appearing on the show because of Fox’s politics.)

Often unmoored from the Washington day-to-day, “Red Eye” resolved at times to subvert cable news itself, once pretending to convene a 16-expert panel to discuss banking reform, only to run out of time after Mr. Gutfeld’s introductions.

Another night, a guest set a guitar on fire.

“He’s like America’s latchkey kid, grown up,” said Nick Gillespie, an editor at large at Reason, the libertarian magazine, and a “Red Eye” regular. “You are constantly searching out new things to pass the day when the adults aren’t around.”

Like media personalities before and since — including Joe Rogan and a constellation of other podcaster-comedians — Mr. Gutfeld took care to convey a vital quality to his audience: that he was getting away with something, saying what should not be said. He names Norm Macdonald, David Letterman and Tim Dillon as favored comedy minds.

Matt Sienkiewicz, a Boston College professor and Mr. Marx’s co-author of “That’s Not Funny,” said Mr. Gutfeld’s emergence was a signal accomplishment for the right: “somehow claiming conservativism or right-wing-ness as being against the squares.”

While “Red Eye” built a loyal following that included a future president — Mr. Trump “called me the next day after ‘Red Eye,’” Mr. Gutfeld said — the host’s trajectory was hardly prodigious.

Inside Fox, plaudits for “Red Eye” could register as backhanded: At least it was popular in Hawaii, executives said, where it aired in prime time.

It was not until 2015 that Mr. Gutfeld transitioned to a more humane hour on the mainland, for a weekend show at 10 p.m.

Around this period, he also often did something that feels disorienting to rewatch, given the host’s present disdain for those who moralize about Mr. Trump: He moralized about Mr. Trump.

“I’ve heard people defend him about making fun of a disability, making fun of John McCain, making fun of women,” he said on “The Five” in December 2015, accusing a Fox colleague of “Trumpsplaining” away his behavior. “No one will ever stop defending the crass stuff he says.”

Before the election, Suzanne Scott, now the chief executive of Fox News Media, hosted Mr. Gutfeld in her office.

Mr. Trump had no chance anyway, he told her.

“She was like, ‘Greg, you should maybe prepare,’” he remembered, “‘for what happens if he wins.’”

In September 2021, eight months after the Jan. 6 riots, Mr. Gutfeld sat across from Mr. Trump at his golf club in Bedminster, N.J.

“The most important question I have to ask you,” Mr. Gutfeld said to begin their interview. “How about my ratings?”

Mr. Trump congratulated him on “beating some very untalented people.” Mr. Gutfeld noted that he had lost friends defending the former president.

“But,” Mr. Trump said, “you also gain friends.”

Mr. Gutfeld has ascribed his shift, with a committed straight face, to a deeds-over-words focus on Mr. Trump’s policies.

“He is a salesman,” Mr. Gutfeld said, cradling his French bulldog, Gus, on his lap in the home the host shares with his wife, Elena Moussa. “Once you understand that, the derangement just kind of washes away.”

This refashioned perspective coincided with a growing platform. His move in 2021 to weeknights at 11 reflected a programming creed of Ms. Scott, who has preferred to cultivate talent internally rather than cast about for fresher faces unfamiliar to viewers. Installing Mr. Gutfeld where an hour of hard news used to be, Ms. Scott reasoned that pandemic-weary audiences needed some levity.

“Gutfeld!” announced its arrival with an opening monologue that named and flamed his new peers.

“Who do they offend?” Mr. Gutfeld asked. “The only time Stephen Colbert ruffles feathers is in a pillow fight. The definition of risk to Kimmel is dehydration from crying too much. Fallon? That guy fawns more than a herd of deer. And I heard Seth Meyers and Trevor Noah ran off to be obscure together.”

While Mr. Gutfeld mostly agrees with other Fox personalities in the lineup of Republican-friendly hours — that progressives are nuts, that Mr. Trump is unduly targeted, that President Biden is a doddering mess — “Gutfeld!” does land differently, with a host who seems adamant that his exclamation point is in on the joke.

“He’s today’s Don Rickles,” Candace Caine, a devotee from Birmingham, Ala., said after a recent taping — her third visit to see Mr. Gutfeld — where she leaned over a railing to shout “I love you!” during a commercial break.

The show leads with politics, mostly, but its gaze can drift. At the taping, the discussion ricocheted from Kanye West to “Ozempic finger” to a Belgian man who crashed his own funeral.

“He was greeted by family and friends,” Mr. Gutfeld said into the camera, “who promptly beat him to death.”

The show operates with a staff of a dozen, according to Mr. Gutfeld, buttressed by two fixtures on the panel: Ms. Timpf — a libertarian commentator who tells friends in New York that she does pornography because, she said, because it is “far less controversial” than naming her employer — and Tyrus, a professional wrestler who lugs a hulking championship belt to each appearance.

“That’s Greg’s whole point: Don’t fit in,” said Tyrus, who met Mr. Gutfeld on Twitter after they found themselves on the same side of an argument. “Make everyone else adjust to you.”

Often, Mr. Gutfeld performatively scolds his crowds for rewarding “red meat” digs at Democrats, objecting recently that audience applause for a guest’s generic Biden slight was “eating into my time.”

“Funny is hard,” said Ann Coulter, a friend and frequent “Red Eye” guest, accusing liberal hosts of virtue-signaling to “status-obsessed audiences.” “Hating the right people is easy.”

But Mr. Gutfeld projects his share of tailored people-hating, too.

Off-air, Mr. Gutfeld said he did not want to be a “mirror image” of comedy on the left, adding that “just calling somebody evil” is not effective persuasion. On-air, he has called Mr. Biden a “Lucifer” who “put a target on whites.”

Off-air, he said he might like to have Representative Alexandria Ocasio-Cortez on his show but worried that she would not be “comfortable.” On-air, the same night, he called her a “not bright” climate zealot who would “shut her gob” if she truly cared about excess carbon dioxide.

“It seems more mean than joking,” said Amanda Carpenter, a “Red Eye” guest and former Republican congressional aide, lamenting Mr. Gutfeld’s tone now. “Owning the libs is the fun.”

His audience has plainly learned as much by now, though even those closest to Mr. Gutfeld can struggle to read him.

During a brief tour of his apartment after the interview, the host lifted the painting of himself as his pup trailed behind, looking startled.

“You all right, buddy?” Mr. Gutfeld asked.

Gus was not. He yelped at the rendering, backing away in apparent confusion: What was art? What was real?

He returned to his pen of toys, seeking comfort and recreation.

“My little guy,” the host said. “He’s not sure if I’m me!”

Kitty Bennett contributed research.


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