This article explores the surprising late-night crossover between Greg Gutfeld and Jimmy Fallon, highlighting their unexpected camaraderie amid the fallout from Stephen Colbert’s cancellation and the ongoing political tensions reshaping the comedy landscape.

In a surprising twist that brought together some of late night’s most unlikely figures, Fox News host Greg Gutfeld appeared on NBC’s The Tonight Show Starring Jimmy Fallon on August 7, 2025.

The reunion sparked curiosity and speculation across the entertainment and political worlds, coming just weeks after President Donald Trump publicly gloated over CBS’s decision to cancel The Late Show with Stephen Colbert—a cancellation that has since ignited fierce debate and reshaped the late-night comedy landscape.

Gutfeld, known for his sharp conservative commentary and for hosting Fox’s Gutfeld!, walked onto Fallon’s stage to a warm, albeit somewhat cautious, embrace.

The two men appeared to sidestep any direct discussion of the recent political controversies swirling around the late-night circuit, including Gutfeld’s pointed criticisms of Colbert’s political style and Trump’s snarky remarks targeting Fallon and other liberal hosts.

Instead, Gutfeld regaled the audience with a lighthearted story from 15 years ago when he first met Fallon in an “illegal speakeasy” tucked away in Hell’s Kitchen, New York City.

“You have no memory of it, which is okay because we were wasted,” Gutfeld joked, adding, “Inside, it looked like a place where special ops forces waterboard terrorists.”

The crowd laughed as Fallon giggled along with the tale, a rare moment of camaraderie between two hosts often positioned on opposite ends of the political spectrum.

Gutfeld’s career trajectory—from hosting the late-night show Red Eye to leading Gutfeld! on Fox—was another highlight of the visit, showing the path that led him back to primetime conservative commentary.

Despite their apparent cordiality, the interview notably skirted around the elephant in the room: Gutfeld’s recent comments on Colbert’s cancellation and President Trump’s gloating remarks.

Just days prior, Trump had boasted on social media, “Greg Gutfeld is better than all of them combined, including the moron on NBC who ruined the once great Tonight Show,” a direct jab at Fallon.

Gutfeld himself had taken shots at his fellow late-night hosts, praising Fallon for “not being afraid to upset his peers” by sitting alongside him.

“Unlike the other guys,” Gutfeld said in an interview with Variety, “Jimmy sitting with me proves he’s not afraid of upsetting his peers or afraid of my mesmerizing charm.”

Gutfeld’s critiques of Colbert were even more biting. Following CBS’s announcement to cancel The Late Show after Colbert’s decade-long tenure, Gutfeld accused the former host of alienating audiences with his “sermonizing” political commentary.

“They didn’t just cancel the show. They canceled the whole show,” Gutfeld asserted.

“This was an institution, and rather than put someone in his place they just said, ‘We’re closing up.’ Imagine being a chef. You’re such a bad chef that they cancel food. … It’s so obvious. You can’t do a comedy show and a sermon at the same time.”

This statement captures a key tension in late-night television: the balance between entertainment and political commentary.

While Gutfeld has built a brand rooted in politically charged humor, Fallon has traditionally steered clear of overt political messaging, opting instead for a more inclusive, lighthearted approach.

However, Fallon did voice his support for Colbert after the cancellation news broke on July 22. “I don’t like it. These are crazy times,” Fallon told viewers.

“Stephen has done years of very smart and hilarious television, and he’s won 10 Emmys.” His comments underscored the respect many in the industry hold for Colbert despite the network’s decision.

The interplay between these two late-night figures—Gutfeld’s unabashed political edge and Fallon’s measured tone—mirrors the larger fractures currently shaking the late-night landscape.

CBS’s cancellation of The Late Show not only removed a longtime staple but also has exposed underlying battles about the direction of late-night comedy: Should it be a platform for biting political satire or a refuge from the harsh realities of today’s divisive political climate?

Fallon’s Tonight Show remains one of the highest-rated late-night programs, largely due to its nonpartisan approach and wide appeal. Gutfeld!, meanwhile, has carved out a niche audience that embraces unapologetic conservatism.

Their unlikely collaboration on Fallon’s stage hints at the possibility of bridging divides, or at least a momentary truce in an increasingly polarized arena.

As late-night viewers watch the aftermath of Colbert’s cancellation unfold, moments like these raise questions about the future of the genre. Will late-night comedy return to an apolitical space, or will it continue to serve as a battleground for ideological clashes?

For now, Fallon and Gutfeld’s surprising on-air reunion offers a glimpse of mutual respect and humor amid chaos, suggesting that even in fractured times, laughter and connection remain possible.

The night ended without any direct mentions of Trump’s recent jabs or the swirling controversies—a subtle reminder that behind the political posturing, the art of comedy still finds room for unexpected friendships and stories from a wild night in Hell’s Kitchen.

With tensions simmering and audiences craving fresh perspectives, the late-night landscape is primed for a new chapter. And as these two stars proved, sometimes the most unlikely duos make the biggest impact.