‘The Five’ roasts Greg Gutfeld in an epic birthday bash

Greg Gutfeld, the king of late-night comedy and unapologetic provocateur, just hit the big 6-0, and his colleagues on The Five weren’t going to let this milestone pass without making him squirm in his seat. If you tuned in expecting the usual political banter, get ready for a different kind of sparring—this time, no politics, just pure roast.

The stage was set, the jokes were loaded, and the roast began in classic The Five fashion: fast, sharp, and irreverent. Here’s what went down.

Judge Jeanine Throws the First Punch

Judge Jeanine Pirro kicked things off, admitting right out of the gate that she didn’t join The Five to engage in intellectual debates or legal breakdowns, but rather to keep an eye on Gutfeld himself. Tossing in a jab about how she probably should’ve hired security to guard her shoes from the notoriously mischievous host, she got the roast rolling with a deadpan delivery.

She went on to make fun of Gutfeld’s “Napoleon complex”—mocking his height with a quip about knee-punching anyone who calls him short. It was a light-hearted start, setting the stage for the rest of the cast to take even more brutal swings.

Jesse Watters Isn’t Holding Back

Jesse Watters had no mercy. Comparing the roast to how Gutfeld supposedly prepares for his late-night shows—stealing jokes written by someone else—Watters delivered his quip with a grin. He also took a shot at Gutfeld’s apparent disdain for public interaction, advising fans to treat him like his wife does: no touching, no talking.

Watters didn’t stop there. He likened Gutfeld to Joe Biden, claiming “they’re both past their prime.” He joked that Gutfeld gets bossed around by his wife, needs cheat sheets to do his job, and that in a past life, Gutfeld was probably hanging out with segregationists. The jabs were relentless but the laughs were louder.

Jessica Tarlov Takes a Swing

Jessica Tarlov aimed her roast straight at Gutfeld’s ears, going after his old age. “You can tell Greg is turning 60 because he can’t even hear the music he picks.” She also accused him of constantly misquoting her from the green room, chalking it up to his supposed memory problems.

The sharpest cut came when she compared debating Gutfeld to handling her toddler, hinting that his argumentative skills might not be as sharp as he thinks. The joke hit hard, leaving Gutfeld chuckling and fans laughing at the truth behind the barb.

Brian Kilmeade’s ‘Special Delivery’

Brian Kilmeade never misses an opportunity to be on camera, and for Gutfeld’s roast, he delivered his jokes with an extra touch of theatrics. Tapping into his reporting skills, Kilmeade told stories about Gutfeld’s questionable fashion choices. With a perfect mix of sarcasm and wit, he presented Gutfeld with a new outfit, saying, “this is your brand-new look, Greg.”

Kilmeade also dug into Gutfeld’s high school past, sharing stories about how Gutfeld attended the same school as legendary athletes like Tom Brady and Barry Bonds. Apparently, Gutfeld wasn’t exactly a standout at school: Kilmeade joked about calling Gutfeld’s high school only to get a 4 AM response telling him to stop asking why Gutfeld wasn’t honored by the school.

And just when Gutfeld thought it couldn’t get worse, Kilmeade topped it off with a joke about Gutfeld once wearing his little brother’s tank top just to get attention on TV.

The Final Blow from Dana Perino

Dana Perino wrapped up the roast by reminiscing about her long working relationship with Gutfeld. She remarked how he was so short when they first started together that they almost rebranded the show as The 4½. Ouch.

Adding to the sting, she shared a recent ‘friendly’ message from none other than Scott Adams, who apparently suggested Greg take a week off, but only after cutting his lawn (extra short, of course).

Even Gutfeld’s family got in on the action. Dana read a message from his child, quipping how if he wanted to live with “a hairy little guy who smells bad and makes strange bodily noises,” he could’ve stayed with one of the puppies from a past litter.

Gutfeld Fires Back

You didn’t think Gutfeld was going to let these jabs slide, did you? True to form, he hit back with some witty responses of his own.

• To Jesse Watters: Gutfeld hit him with a joke about promoting conspiracy theories, particularly the one where women might find him attractive. He added another layer by saying Watters has inspired plenty of people to talk to their doctors—about back hair and erectile dysfunction.
• To Jessica Tarlov: He praised her ability to juggle motherhood with her work, but added a brutal punchline: “You still sound like a childless cat lady.”
• To Brian Kilmeade: Gutfeld mocked Kilmeade’s string of coffee table books, suggesting they’d be perfect to fix a wobbling table leg.

And finally, to Dana: “I’ve never been roasted by someone who’s too short to operate an oven.” It was the perfect zing to match all the short jokes aimed his way.

Gutfeld took the roast like a true comedian—grinning through the hits and slinging some scorching comebacks of his own.

Wrapping Up: A Roast for the Ages

Turning 60 doesn’t faze Gutfeld, and if this roast proves anything, it’s that his wit, charm, and ability to laugh at himself are still strong.

The Five crew laid it on thick, throwing jokes that ranged from his height to his fashion to his tendency to rile up audiences. Through it all, Gutfeld laughed and dished it right back. It was a roast filled with the same energy and irreverence that’s made Gutfeld a constant force in the late-night scene.

So, here’s a toast to the king of late-night, Greg Gutfeld—long may he roast and be roasted. Even if he’s slowly inching toward needing a hearing aid to catch his audience laughing.

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What’s your favorite roast from the show? Drop it in the comments below—you know Gutfeld can take it!