The conversation began with an admission of mutual chaos. On a recent episode of The Tonight Show, cable news firebrand Greg Gutfeld sat down with host Jimmy Fallon, but before they could even discuss Gutfeld’s newest projects, Fallon brought the conversation to a screeching, hilarious halt, dredging up a shared, drunken memory. It was a story so bizarre and specific—involving an illegal speakeasy, wrestling, and a shocking anti-smoking intervention—that it instantly framed Gutfeld’s entire career as the product of beautiful, unpredictable pandemonium.

The shocking anecdote, which Gutfeld was initially unable to recall, painted a vivid picture of a makeshift, speakeasy-style bar in Hell’s Kitchen, described by Fallon as looking like a “shipping container” and a place where “special ops forces waterboard terrorists.” Amidst this unsettling ambiance, Fallon recounted seeing Gutfeld, whose eyes “just kind of explode,” run toward him and tackle him “like a giant golden retriever.” What followed was a round of wrestling, first with Fallon, then with his friend Andy.

The truly memorable—and bizarre—moment, however, came when Gutfeld abruptly stopped the roughhousing. Fallon had lit a cigarette, a costly habit in New York City. Gutfeld snatched the cigarette, crinkled it dramatically, and tossed it away, declaring, “These things will kill you.” When Fallon protested, pointing out that Gutfeld, being rich, could afford to lecture him while Fallon was not, Gutfeld’s face suddenly “changed,” and he looked “sad” before leaving. A short while later, he returned with a fresh pack of Parliaments, handing them over—a gesture Fallon accepted with the wry observation, “That was really sweet. You want me to die.”

But the anarchy didn’t end there. After the dramatic gift exchange, Gutfeld suggested moving to another bar. They piled into the back of his car, complete with a driver, took a quick turn, and arrived at a new location. In a twist of surreal comedy, Fallon realized they had merely driven from one door of the building to another door of the very same building. The host surmised Gutfeld simply “wanted to impress that you had a driver.” This introduction—a tale of drunken moralism, wrestling, and theatrical absurdity—was the perfect prelude to discussing the highly unconventional, yet profoundly successful, career path of the man who hosts a top-rated late-night show.

The Unexpected Path: How Being Fired Becomes a Blessing

Gutfeld’s trajectory, it turns out, is a masterclass in turning failure into fuel. When Fallon asked about his background and how he ended up hosting his current talk show, Gutfeld’s immediate, almost proud answer was: “I’ve been fired a lot.” This declaration, delivered with the kind of unflinching honesty Gutfeld is known for, immediately resonated with the audience, offering a deeply human take on professional setbacks.

He emphatically stressed that being fired, contrary to popular fear, is “the best thing in the world.” This simple, powerful piece of advice—that you “always end up someplace better”—served as the emotional core of his career story, transforming a narrative of professional rejection into a testament to resilience and upward mobility.

Gutfeld detailed a dizzying sequence of high-profile firings that reads like a rogue’s gallery of magazine publishing. He was fired from Men’s Health, where he was, hilariously, the “king of abs,” having authored the seminal fitness guides Five Minutes to Flat Abs and its thinly disguised sequel, Six Steps to a Firm Belly. He then moved on to Stuff magazine, where he was also eventually fired, and then Maxim, an experience so eventful that he was forced to “leave the country” for a stint in the UK, where he was—you guessed it—fired again.

This chaotic professional history led him, at a point when he was “broke,” to accept a lifeline: an offer from Fox News to host a late-night show. That show was Red Eye.

Speed Dealers, Breastfeeders, and the Edginess of Late-Night

Gutfeld described the frenetic, bare-bones launch of Red Eye. The network told him they were starting soon, with rehearsals taking place in the green room where “Everybody was drunk. Even the cameramen.”

The show, which aired late at night, quickly ran into a surprising bureaucratic hurdle: it was deemed “too edgy” for its initial slot. The solution was not to tone down the content, but to push the start time back further. Thus, Red Eye was relegated to a very late slot, an hour where, as Fallon mused, “Who’s watching TV?”

Gutfeld had the answer, based on a memorable focus group. The demographic for television in that deep-night hour, he cheerfully informed Fallon, consisted of “speed dealers and breastfeeders,” along with a significant audience of inmates. This unique, wide-awake, and highly engaged viewership provided some of the show’s most dedicated fans, with letters from prisoners often asking him to “set them up with the guests.”

The Senior Correspondent Who Couldn’t Handle the Skirts

One of the most heartwarming, and yet still highly characteristic, aspects of Gutfeld’s early success was the role played by his mother. He proudly revealed that his mom was actually a big part of the show, earning the title of a “senior correspondent.”

Her job was incredibly simple, yet vital: to watch Fox News all day and summarize the news for him. However, Gutfeld’s mother was far more concerned with sartorial matters than geopolitical ones. Her recurring complaint was about the attire of the female correspondents. “All the women wore short skirts,” Gutfeld recounted, quoting his mom: “She says, ‘I don’t need to see their you know what.’”

Gutfeld’s admission that his mother was an integral part of his career success tapped into a profound emotional truth: the value of unconditional parental support. He noted that while growing up, he was embarrassed by his parents, but his friends loved his mom. In fact, he’d sometimes come home to find his friends already there, “in the backyard with my mom,” having essentially “dumped me for my mom.” This experience, he said, taught him that she was genuine, “no B.S.,” and a fierce supporter of everything he did. Her pride in seeing him succeed on Red Eye and The Five was a huge, defining factor in his journey, serving as a powerful reminder of what truly grounds a life lived in the public spotlight.

The Game Show that Pays Less than Historical Television

Finally, Gutfeld promoted his new game show, What Did I Miss?, a concept that is as clever as it is inherently absurd. The premise is built around the modern phenomenon of sequestration—specifically, people who go into shows like The Bachelor or Love Island and miss all the major news events.

The show literally sequesters people in a house upstate, isolating them completely—no phones, no news—for a long duration. When they emerge, they are quizzed on the news they missed, a challenging task, Gutfeld noted, in an era where distinguishing “Fake or false” is nearly impossible, especially with political figures.

The highlight of the promotion, however, was Gutfeld’s astonishing revelation about the prize money. While he claimed the show was “amazing,” he also admitted, “The best part about this show is, we didn’t pay ‘em anything.” He clarified that the prize was a specific amount for the long period of isolation. He calculated that after taxes, the contestants almost “owe us money.”

Comparing it to a historical TV show where contestants could win the same amount for one puzzle, Gutfeld underscored the absurdity of the prize money for the long period of sacrifice. Though the amount was raised, Gutfeld jokingly expressed a desire to bring it “back down to the original amount.” Fallon immediately challenged this, insisting that long-term sequestration demands a much larger prize. The financial irony of the show perfectly encapsulates Gutfeld’s persona: a blend of shrewd business, self-deprecating humor, and a fascination with the bizarre details of modern life.

Greg Gutfeld’s interview was more than a promotional spot; it was an unfiltered memoir. From the wrestling chaos of a New York speakeasy to the unceremonious firings that propelled him forward, and from the loving, opinionated presence of his mother to the delightfully stingy premise of his new game show, Gutfeld proved that the path to being a prominent voice in current affairs is often less about a straight line and more about embracing the beautiful, unpredictable madness of life. His success is a potent reminder that often, the biggest setbacks are merely setup for the greatest comebacks.