Greg Gutfeld has become one of the most prominent figures in late-night television, but his rise to fame wasn’t without its setbacks. In a candid interview on The Tonight Show, Gutfeld took a trip down memory lane, recounting the many times he was fired, rejected, and, in some ways, reinvented himself. But it was this very journey, marked by failure, that set the stage for his eventual success at Fox News, culminating in his hit talk show What Did I Miss?

Gutfeld’s story is one of resilience and reinvention, filled with stories of struggles, comical moments, and an undying drive to find his place in the entertainment world. His blunt humor and unapologetic approach to life have earned him a loyal following, but his path to success wasn’t always paved with gold.

From Magazine Gigs to Late-Night Fame: Gutfeld’s Tumultuous Career

Many people know Greg Gutfeld as the host of Gutfeld! and a key personality on The Five, but before he became a household name on Fox News, his career took several unexpected turns. As he revealed in the interview, Gutfeld’s journey started with a series of professional setbacks.

“I’ve been fired a lot,” Gutfeld laughed as he recounted his earlier career. “You think firing is bad? It’s the best thing in the world. People think it’s a disaster, but you always end up somewhere better.” This belief in the silver lining of rejection became a recurring theme in Gutfeld’s career.

His first major setback came when he was let go from Men’s Health, where he had written popular pieces like “Five Minutes to Flat Abs.” Despite his success, Gutfeld found himself out of a job, but he quickly moved on to Stuff magazine, where he was let go again. And that was just the beginning. He continued to hop from job to job, experiencing the highs and lows of the media industry. “I got fired from Maxim too,” he said. “Had to leave the country. Let’s not get into that.”

It’s a story that Gutfeld now reflects on with a sense of humor. However, those years of rejection shaped him into the person he is today. “I didn’t give up. I kept going,” he says. “And eventually, I ended up at Fox.”

The Birth of ‘Red Eye’ and the Drunken Rehearsals: The Birth of an Icon

In a dramatic twist, Gutfeld’s eventual break came when a friend suggested that Fox News wanted to launch a late-night show. Without hesitation, Gutfeld jumped at the opportunity, even though his bank account was running on empty. “I was broke. I’ll do anything,” he joked, recalling his initial reluctance.

Thus, Red Eye was born—a late-night, edgy show that aired at 2 a.m. After a whirlwind, barely-there rehearsal process (in a green room, with drunk crew members), Red Eye hit the airwaves. “They thought it was too edgy for 2 a.m. so they moved it to 3 a.m.,” Gutfeld laughed. “We did a focus group for the 3 a.m. slot, and it turned out the main audience was people on speed and people breastfeeding.”

Gutfeld’s sharp wit, paired with an unconventional approach to late-night television, garnered attention from those who were willing to stay awake at odd hours. What seemed like an absurd, half-baked show turned into a cult favorite that set the stage for his future success.

From ‘Red Eye’ to Prime Time: Gutfeld’s Rise to Fox Stardom

It wasn’t long before Gutfeld’s show took off, leading to his eventual promotion to the co-hosting gig on The Five and ultimately becoming the star of Gutfeld! But Gutfeld’s evolution didn’t stop there. He’s continued to evolve as a host, moving from controversial late-night antics to a more polished but still edgy prime-time talk show.

He credits his success to his willingness to take risks, break boundaries, and, most importantly, not shy away from being his authentic self. “It’s important to not hold back,” Gutfeld stated. “If you don’t say the things other people are thinking, then what’s the point?”

‘What Did I Miss?’: The Latest Wild Idea

In addition to Gutfeld! and The Five, Gutfeld is now hosting the new game show What Did I Miss? which takes an unconventional, humorous approach to current events. The premise of the show is simple yet captivating: sequester contestants for days, cutting them off from the news, and then quiz them about current events when they emerge.

While it may sound like a gimmick, Gutfeld’s ability to blend humor with insightful commentary has resonated with audiences. As he explained, “I just thought, people who come out of seclusion like on The Bachelor or Love Island—they have no clue what’s going on. We put them in a house, and they miss everything. Then we quiz them on the news. It’s like the perfect setup.”

But what truly sets the show apart is Gutfeld’s twist on what could easily be another cookie-cutter game show. “We didn’t pay them anything. $25,000 for 100 days,” he said, describing the contestants’ compensation. “If you work out the math after taxes, they owe us money.” A humorous jab at how little contestants were paid, Gutfeld’s unfiltered style shines through once again.

Behind the Humor: Gutfeld’s Strong Family Support System

As much as Gutfeld is known for his biting humor and sharp political insights, he’s also quick to acknowledge the importance of family, especially his mother, who was integral to his career. Gutfeld’s mother was given the title of senior correspondent for the show and had a unique job—watching Fox News and reporting on the news of the day to him. “She’d be upset about the skirts the women on Fox wore, but she was my biggest supporter,” Gutfeld says. “She’d watch my shows, and she always had my back.”

Her support, along with his wife’s and friends’ encouragement, helped Gutfeld stay grounded through the highs and lows of his career. “When you’re in the media, you need that support. It’s everything,” Gutfeld emphasized.

Conclusion: Gutfeld’s Unlikely Success and Future

From being fired from multiple jobs to eventually finding success at Fox, Greg Gutfeld’s journey is a testament to the power of persistence, adaptability, and a willingness to take risks. His unique perspective, wit, and bold humor have made him a household name. Whether he’s hosting What Did I Miss?, The Five, or Gutfeld!, he continues to push the boundaries of late-night television and prove that sometimes, rejection is just a stepping stone to greatness.

As Gutfeld himself puts it, “The key to success is not to fear failure. You fail a lot, but eventually, you land somewhere better.” And judging by his career, it seems he was right all along.