NEW YORK, NY — Greg Gutfeld is one of Fox News’ most recognizable personalities, with his late-night program Gutfeld! dominating cable ratings and his seat on The Five making him a fixture in American political debate. But according to Gutfeld himself, his path to television’s top tier wasn’t a straight climb — it was a zigzag marked by layoffs, unexpected pivots, and a knack for turning failure into opportunity.

And now, with his latest side project — a game show called What Did I Miss? — he’s proving that reinvention isn’t just a survival skill; it’s part of his brand.

From Magazine Writer to Serially Fired Editor

Long before he was debating policy and cracking late-night jokes, Gutfeld was deeply embedded in the print media world. He made his name at Men’s Health in the 1990s, writing pieces like “Five Minutes to Flat Abs” and a follow-up called “Six Steps to a Firm Belly.”

“Yes, I cornered the market on abs,” he joked during a recent late-night interview. “I was raising a family of abs.”

But his time at Men’s Health ended abruptly when he was fired — a fate that would repeat itself more than once.

After Men’s Health, Gutfeld became editor of Stuff magazine, helping turn it into a glossy men’s lifestyle publication. But after a few years, another pink slip arrived. He then landed at Maxim, which eventually took him to the UK, where, as he puts it, “I had to leave the country — let’s not get into that.”

“Getting fired sounds bad,” Gutfeld said. “But every time it happened, I ended up somewhere better. People think, ‘Oh my God, I’m fired, what am I going to do?’ But for me, it opened the next door.”

A Chance Encounter That Changed Everything

It was a casual bar conversation in New York’s Chelsea neighborhood that set Gutfeld on the path to Fox News. A friend mentioned that Fox was looking to launch a late-night show.

“I was broke, so I said, ‘I’ll do anything,’” Gutfeld recalled.

Three days later, he was at Fox’s studios preparing to launch Red Eye, a quirky, irreverent panel show that aired at 2 a.m. The rehearsal space? The green room. The vibe? Less “corporate news” and more “after-hours comedy club.”

“Everybody was drunk — even the cameramen,” Gutfeld laughed.

Red Eye was unapologetically weird, mixing pop culture commentary with absurdist humor. But it was also considered “too edgy for 2 a.m.” by network brass — so they moved it to 3 a.m.

“We did a focus group,” Gutfeld joked. “Turns out the audience was speed dealers and breastfeeders. If you needed your speed and your baby fed, you watched my show.”

From Cult Following to Prime-Time Player

Despite its odd time slot, Red Eye developed a devoted audience, including a surprising number of prison inmates who wrote letters asking Gutfeld to set them up with female guests.

By the early 2010s, Gutfeld had carved out a unique niche at Fox, leading to his move to The Five, the network’s 5 p.m. political roundtable. His quick wit and willingness to needle co-hosts from across the political spectrum made him a breakout star.

Then came Gutfeld! in 2021, a late-night talk show that took direct aim at the traditional broadcast comedy model. Within months, it was consistently beating network competition in the ratings.

But Gutfeld has never been content to stay in one lane — which brings us to his latest project.

‘What Did I Miss?’: A Game Show for the News-Oblivious

The premise of What Did I Miss?, streaming on Fox Nation, is deceptively simple: take a group of people, cut them off from the outside world for weeks, and then quiz them on the news they’ve missed.

Gutfeld says he was inspired by reality dating shows like The Bachelor or Love Island, where contestants are sequestered without phones or internet access.

“They come out and have no idea who was elected president or that their spouse left them for the maid,” he said. “I thought, ‘That’s the show.’”

So he put participants in a remote house “where a family goes missing” — his words — stripped them of electronics, and let the news cycle pass them by.

When they emerged, contestants were confronted with true-or-false headlines. With the unpredictable Trump era as a backdrop, the game became a test of both news literacy and absurdity.

“Imagine someone says, ‘True or false: The president demands an annexation of Canada.’ You’d think, ‘No way.’ But if it’s Trump, maybe yes. That’s the beauty of it.”

The Prize That Made Contestants Owe the Show Money

If the concept wasn’t unusual enough, Gutfeld revealed the original prize money was $25,000 for 100 days — a figure so low that, after taxes, “they owed us money.”

“Back in 1980, The $25,000 Pyramid gave you that for one puzzle,” he said. “We made them sit in a house for 100 days for the same amount.”

After some backlash (and possibly guilt), the prize doubled to $50,000. Even so, Gutfeld joked about “bringing it back down to 25.” His interviewer suggested $100,000 for 100 days, which Gutfeld pretended to consider before admitting the budget probably wouldn’t stretch that far.

Why He Thinks the Show Works

What makes What Did I Miss? compelling, Gutfeld argues, is the mix of personalities. Despite being isolated for weeks, the contestants in season one remained “remarkably sane,” which he attributes to careful casting.

The real entertainment, though, comes from seeing how out-of-touch people become when they’re unplugged. In an era when news breaks in seconds and social media amplifies everything, the gap between reality and perception widens fast.

“It’s fake or false — and you can’t always tell,” Gutfeld said. “Even when you’re following the news, half the time you can’t tell.”

Family, Support, and On-Air Honesty

Gutfeld also credits his late mother for shaping his career and on-screen persona. He affectionately dubbed her a “senior correspondent” when she would watch Fox News and feed him daily notes — often complaining about the short skirts worn by anchors.

“She didn’t mince words,” he said. “She was no B.S. and supported everything I did.”

Her presence in his life, and later her absence, underscored the value of authenticity in a business that often thrives on artifice. It’s a principle that seems to run through Gutfeld’s projects, from Red Eye to What Did I Miss?.

From Tackle-Hugging to Television Mainstay

In the same late-night segment, Gutfeld heard a hilarious story from a fellow entertainer about a chaotic night in a tiny Hell’s Kitchen speakeasy 15 years ago. The tale involved Gutfeld tackling the storyteller “like a giant golden retriever,” confiscating and then replacing a cigarette, and inexplicably taking a chauffeured ride from one door of a building to another.

It was a reminder that beneath the sharp-tongued political humor and media critiques, Gutfeld is just as comfortable being the butt of the joke.

What’s Next

With What Did I Miss? renewed for another season and Gutfeld! continuing to dominate late-night cable, Gutfeld shows no signs of slowing down. He credits his staying power to the same adaptability that kept him afloat through years of firings and reinventions.

“The key,” he says, “is not being afraid to move on. Every time I got fired, I ended up someplace better. If you’re willing to keep trying, it’s never the end.”

For viewers, that means more late-night debates, more absurd game show questions, and more moments where you can’t quite tell if he’s being serious. For Gutfeld, it means doing exactly what he’s been doing since the days of abs articles and 3 a.m. cult TV — turning unpredictability into an advantage.