Rosie O’Donnell has spent nearly 20 years getting under Donald Trump’s skin.
Four nights on late-night television by one of his nemeses apparently did the trick again.
A series of Trump jokes set off the White House, which publicly unleashed a shocking remark about the omedian and talk show host.
O’Donnell spent last week guest-hosting “Jimmy Kimmel Live!” turning her longtime nemesis into a nightly punchline. She mocked his hair and his dancing, turning their feud into an episode of “High School Musical.”
By Friday, officials at the White House had clearly heard enough.
White House spokesperson Davis Ingle told Entertainment Weekly that “Rosie O’Donnell is a nasty woman and a total slob whose brain has been completely destroyed by Trump Derangement Syndrome.”
Calling O’Donnell a “slob” was a choice that did not sit well with the comedian.
The Emmy winner took to Instagram and did what she has done so often: teased him. She quickly posted a 2024 photo of Trump at Trump International Golf Club West Palm Beach. He wore a white polo tucked into blue pants. His black belt sat unusually high on his waist. The snapshot showed that the president has little room to talk about anyone being sloppy.
Her caption read: “This is the guy calling me a slob #mirrormirror.”
Her Instagram followers immediately pulled up a chair and joined the roast.
“Get him Rosie!!!” one person wrote. Another added, “He’s so fkng jealous of your badassery.”
“Belt is the same size as the equator,” one commenter joked. Someone else quipped, “Belts are not meant to be that close to nipples. Just saying.”
“If those pants go any higher they’re gonna have deodorant stains on them,” a follower cracked.
“And this is even too nice of a photo choice for Oompa J Loompa,” another added.
“Looks like he’s wearing the Michael Meyers mask. Freaking me out,” one follower wrote. Another seemed baffled by what they were seeing. “And this is where I keep getting confused because are people not SEEING THIS?! Or hearing the way he speaks ??”
Of course, the White House was not wandering into some fresh celebrity squabble.
This beef began in December 2006. O’Donnell criticized Trump on “The View” over his handling of the Miss USA controversy involving Tara Conner. Trump responded by calling O’Donnell a “loser” and a “woman out of control.”
The insults never really stopped.
By August 2015, their feud had graduated from daytime television to a Republican presidential debate. Megyn Kelly questioned Trump about derogatory remarks he had made about women. Trump quickly interrupted her, stating, “Only Rosie O’Donnell.”
The feud followed Trump into the presidency and beyond.
In July 2026, Trump even threatened to revoke O’Donnell’s U.S. citizenship. Legal experts noted that a president does not have the authority to simply strip a natural-born American of citizenship.
O’Donnell had already moved to Ireland in January 2025 after Trump won the 2024 election. She later said reading Project 2025 helped influence her decision. She has said she may return permanently when she believes the country is safe and equitable.
An ocean has done absolutely nothing for the peace process.
During her August 2026 Kimmel takeover, O’Donnell performed “Donny Boy,” her Trump-themed rewrite of “Danny Boy.”
“Oh, Donnie boy, it’s Rosie, Rosie calling,” she sang. She also advised him to “drop that Big Mac.”
Then came the political jabs.
“Poor Donnie boy, your polls, your polls are falling,” O’Donnell sang. She also mocked his hair, inflation, late-night posting and the green Reflecting Pool.
She eventually delivered her proposed solution.
“We all know you’ll never be Obama,” she sang. “Why not resign and make this country great again?”
It was not even her first attempt at turning Trump into musical theater.
O’Donnell previously revealed that she rewrote “If I Only Had a Brain” from “The Wizard of Oz” for Kimmel. She said the number was rejected from the network for being too political. So, she took it somewhere else.
The “League of Their Own” actor performed the song on Kara Swisher’s podcast.
“His approval rate is 30. His diapers always dirty. I think the guy’s insane,” she sang. She later added, “He ain’t no stable genius.”
Apparently, blocking one Rosie O’Donnell Trump song only guarantees another. And after two decades of insults, O’Donnell has learned something else. If Trump calls you a slob, skip the argument. Post the picture.
Leave a Reply