Greg Gutfeld Heads Into “Enemy Territory” With Scheduled Appearance on Jimmy Fallon’s Tonight Show

In a move that few in television saw coming, Fox News’ sharp-tongued provocateur Greg Gutfeld is set to appear on NBC’s The Tonight Show Starring Jimmy Fallon next week. The outspoken host of Gutfeld! and co-host of The Five made the announcement Thursday, setting off a wave of speculation about what will happen when one of conservative media’s most combative figures steps into one of late-night television’s most liberal-leaning spaces.

A Bombshell Booking

Gutfeld revealed the news on The Five in typically casual fashion.
“I am doing Jimmy Fallon next week,” he said. “I’m psyched about it because Fallon comes across as a great guy.”

Then came the remark that sounded less like a compliment and more like a warning:
“Me going on his show shows he’s not worried about upsetting his peers.”

Translation: Fallon is risking backlash from his late-night colleagues and much of his progressive audience by offering a platform to someone who has built his brand on mocking the very world Fallon inhabits.

For Fallon, the decision to book Gutfeld is anything but routine. With The Tonight Show navigating declining ratings and lingering fallout from internal NBC tensions, bringing on a Fox News star is a gamble with no guaranteed payoff.

The Colbert Connection

The timing is noteworthy. Gutfeld’s announcement comes just days after CBS confirmed that The Late Show with Stephen Colbert, often the centerpiece of anti-Trump sentiment in late-night, will end next year. While other hosts voiced public support for Colbert, Gutfeld remained silent. Now, he’s heading to Fallon’s show — Colbert’s direct competitor — in what some insiders see as a calculated “power flex,” while others are calling it a declaration of war in the late-night ratings arena.

Defending Fallon’s Trump Moment

Gutfeld used his announcement to revisit one of Fallon’s most controversial moments — the 2016 episode when Fallon tousled then-candidate Donald Trump’s hair. The lighthearted gesture drew heavy criticism from the left, with accusations that Fallon had “humanized” Trump.

“Remember, he got a lot of stick for humanizing Trump,” Gutfeld said. “But it didn’t come from anybody but the people on the left who wanted to teach all entertainers a lesson: if you dare show that Trump is a human, then you’re toast.”

Gutfeld concluded with a smirk: “So it’s kind of nice that he’s taking this risk.”

NBC’s Quiet Approach

NBC confirmed that Gutfeld will appear on the Thursday, August 7 episode of The Tonight Show. But notably, Fallon himself has said nothing — no tweet, no teaser, no segment preview. In the competitive world of late-night, where guest announcements are often part of the pre-show hype machine, the silence is striking.

Sources at NBC say some senior producers are “nervous” about the optics. Others argue Fallon is trying to “break the mold” and surprise viewers. One anonymous producer acknowledged the potential stakes:
“Look, we know Gutfeld’s going to go viral — for better or worse. The question is: are we ready for the backlash?”

A Ratings Rivalry With History

For Gutfeld, the appearance is personal. Over the past two years, Gutfeld! has consistently outperformed traditional network late-night shows in total viewers, including The Tonight Show, Jimmy Kimmel Live!, and Late Night with Seth Meyers. His program’s blend of political commentary and humor has attracted audiences who abandoned the established late-night lineup after the pandemic.

He has openly derided mainstream comedians as “predictable,” “partisan,” and “out of touch,” and he has mocked Fallon, Kimmel, and Meyers on air. Stepping onto Fallon’s stage isn’t just a booking — it’s a symbolic entry into enemy territory.

What to Expect on August 7

The big question: What kind of Greg Gutfeld will show up?

Will he play nice, sticking to banter and light comedy? Or will he use the opportunity to launch verbal grenades at the late-night establishment?

Will Fallon challenge him on politics and culture, or serve up softballs for easy laughs?

Viewers may also have their own reactions. Some will tune in out of curiosity, others might boycott in protest, and a few might be looking for the viral moment NBC is surely hoping for.

The Risk for Fallon

Inviting Gutfeld could be seen as a rare moment of ideological openness in late-night television, which in recent years has tilted heavily progressive. But it could also alienate Fallon’s core audience and colleagues in the industry. Fallon has weathered controversy before — the Trump hair-tousling moment still lingers in his public image — and another politically charged flashpoint could either hurt or help him, depending on how the encounter unfolds.

Gutfeld’s Possible Playbook

Gutfeld thrives on unscripted, unpredictable exchanges. On his own show, he’s built a brand around challenging conventional narratives and poking at cultural fault lines. Fallon’s studio, with its upbeat vibe and feel-good energy, may not be built to contain that kind of volatility.

If Gutfeld comes armed with biting jokes and sharp political observations, the segment could break from the usual Tonight Show tone. Whether that’s good for Fallon depends on how the host manages the balance between comedy and confrontation.

A Moment for Late-Night’s Future

This booking comes as the entire late-night landscape is shifting. Colbert’s departure will leave a vacuum. Kimmel, Fallon, and Meyers are all contending with reduced viewership compared to their pre-pandemic highs. Gutfeld, by contrast, has built a program that thrives outside the traditional network model and appeals to a politically different audience.

If his appearance draws big ratings and online buzz, it could encourage other late-night shows to book more ideologically diverse guests — or it could serve as a cautionary tale for why they don’t.

Cold War or Ceasefire?

Gutfeld’s upcoming debut on The Tonight Show could mark the start of a new era in late-night — one where ideological divides are crossed more often — or it could be remembered as a one-off stunt.

For NBC, it’s a calculated gamble: the network is betting on the draw of an unpredictable guest to shake up its format and spark conversation. For Gutfeld, it’s a chance to plant the Fox News flag in one of late-night’s most hallowed studios and prove that he can command attention outside his home turf.

Whatever happens on August 7, it will be more than just another celebrity interview. It will be a collision of two television worlds that rarely share the same stage, and it has the potential to create one of the most talked-about moments in late-night this year.

When Greg Gutfeld walks onto Fallon’s stage, there will be no scripts, no safety nets, and no guarantee that the Tonight Show can contain him. And that, perhaps, is exactly why everyone will be watching.