Greg Gutfeld Reveals His All-Time Favorite Comedic Moment from Trump [WATCH]

A recent exchange between conservative media figures Benny Johnson and Greg Gutfeld highlighted what Gutfeld described as one of President Donald Trump’s most memorable comedic moments, focusing on Trump’s timing and instinctive response during a high-profile public appearance.

During the conversation, Johnson asked Gutfeld to identify his single favorite example of Trump’s humor, noting Trump’s long history of unscripted remarks that have resonated with audiences both on and off the stage.

“What is your single favorite Donald Trump last question, single favorite Donald Trump comedic moment, either behind the scenes, maybe you witnessed or something that was on stage, but as the most successful comedian in the industry, what’s your favorite Trump comedy moment?” Johnson asked.

Gutfeld responded by pointing to what he described as a defining moment that demonstrated Trump’s natural comedic instincts.

He said the exchange stood out among many others because of how Trump anticipated the situation and delivered a line that immediately connected with the audience.

“You know what? I got to go with the all time classic. You know, there’s so many, but the all time classic that got me out of my chair and go, That’s the man was when he said, to be fair, it was Rosie O’Donnell that that was, that was pure comic timing,” Gutfeld said.

Gutfeld explained that the moment stood out because Trump appeared to recognize the direction of the question before it was fully asked and chose a response that cut through expectations.

This Could Be the Most Important Video Gun Owners Watch All Year

“He was seeing the question coming. He could have, he pure Republican response would be, of course, that was in the past. I don’t think like that anymore. I’ve, you know, there are times when I you know, it was for entertainment purposes,” Gutfeld said.

Instead, Gutfeld said Trump rejected a conventional political answer in favor of a line that immediately landed with the audience.

“But that’s not what he did. He said, to be fair, it was Rosie O’Donnell, and I’m sure that it wasn’t just me. I’m sure millions of people got up from the chair and go, that’s the guy,” Gutfeld said.

🚨 TEN YEARS AGO, America fell in love with Donald Trump

On August 6, 2015, Candidate Trump HUMILIATED Rosie O’Donnell in front of MILLIONS, saying he “ONLY” called Rosie a fat pig 🤣

Trump PROVED that he would NOT back down to the woke mob

This was absolutely legendary 😂… pic.twitter.com/ZIqd1JLYxw

— Nick Sortor (@nicksortor) August 8, 2025

Johnson reacted enthusiastically to Gutfeld’s response, emphasizing the reaction it generated and Gutfeld’s own standing in comedy.

“Who wants Greg Gutfeld to do stand up for the next hour? The King of Comedy, ladies and gentlemen,” Johnson said.

WATCH:

I asked Greg Gutfeld what his favorite President Trump moment is.

His answer: The iconic fat pig Rosie O’Donnell roast during the GOP primary debate in 2015. 🤣

“You know what? I gotta go with the all-time classic. You know, there’s so many, but the all-time classic that got… pic.twitter.com/hZamd0NcyM

— Benny Johnson (@bennyjohnson) December 20, 2025