Rosie O’Donnell wrapped up her guest-hosting run on late-night television on Thursday, August 20, 2026, capping a week of sharp monologues on “Jimmy Kimmel Live!” that kept President Donald Trump squarely in her crosshairs — and, she made clear, the feeling was mutual.
The comedian, 64, kicked off her guest-hosting stint on Monday, August 17, filling in for comedian and late-night host Jimmy Kimmel during his absence. From the moment she walked out, the studio crowd made its feelings known, breaking into chants of “ROS-IE” — an echo of her years fronting “The Rosie O’Donnell Show” from 1996 to 2002.
O’Donnell wasted no time turning her opening monologue into a vehicle for something considerably sharper than nostalgia. She opened by acknowledging two audiences at once: the studio crowd and, she suggested with a grin, one particular viewer in Washington. “Hi, I know you’re watching!” O’Donnell said — a wave and a smile directed straight at the camera.
From Ireland to the “Kimmel” Desk
O’Donnell used the platform to address her decision to relocate to Ireland in January 2025, following the 2024 presidential election. On Monday, she told the audience she had been living abroad because of what she called “Mango Mussolini” — one of several colorful nicknames she deployed for Trump throughout the week, alongside “President Oompa J. Loompa” on Tuesday and “President Petty Roosevelt” on Wednesday.
Her child, Clay, who was 11 at the time, made the move with her. O’Donnell said she told Clay to keep quiet about the plan, but Clay promptly informed the entire sixth-grade class that the president hated their mother. Clay’s reported addendum, as O’Donnell told it: “But in all fairness, I believe my mother hates him more.”
She also drew a wry comparison between the political climate she grew up covering and the present moment. Reflecting on her daytime talk show days, O’Donnell noted that the ’90s featured a war in the Middle East, a planet under environmental stress, and a president embroiled in scandals — before deadpanning that today, by contrast, “everything is so chill.”
A Feud Two Decades in the Making
The O’Donnell-Trump feud stretches back to 2006, when O’Donnell criticized Trump while co-hosting “The View,” questioning his standing to lecture others on morality. What began as tabloid fodder escalated dramatically over the years.
During the 2015 Republican primary debates, moderator Megyn Kelly pressed Trump about his history of disparaging remarks toward women — and Trump responded with three words: “only Rosie O’Donnell.” He brought her up again in his first general election debate against Hillary Clinton.
In the summer of 2025, Trump threatened on social media to revoke O’Donnell’s citizenship, writing that because she was “not in the best interests of our Great Country,” he was “giving serious consideration to taking away her Citizenship.” Legal experts noted that a president cannot strip citizenship from a native-born American, but the threat drew widespread attention.
In July 2026, O’Donnell appeared on the cover of PEOPLE magazine and reflected on what she described as the surreal quality of the ongoing feud. She said it was “very strange to have supposedly the most powerful man in the world be your archnemesis” after two decades of being used as a punchline. She called the whole arc — a stand-up comic mocks a reality television host, who then becomes president and keeps her in his sights for 20 years — almost impossible to believe as a matter of lived experience.
Trump’s Correspondents’ Dinner Swipe Lands Flat
The timing of O’Donnell’s return to American television carries its own irony. At the White House Correspondents’ Dinner held Friday, July 24, Trump attempted to mock O’Donnell, claiming she had been “desperate to come back to the United States” but that “nobody wanted her to come back.” The joke proved both unfunny and inaccurate: O’Donnell had already returned to the country before Trump delivered those remarks, having opened a new comedy show at Manhattan’s Daryl Roth Theater.
The show centers on her life and her long-running feud with Trump. She also appeared on “Late Night with Seth Meyers” on the Thursday before her “Kimmel” run began.
Trump’s remarks at the dinner also included calling O’Donnell “a sick young woman. Sick older woman, I guess now I have to say” — a line that drew pushback from observers who noted the president, 80, was revisiting grievances that predated many of his current supporters’ political memories.
Wednesday’s Monologue and What Comes Next
On Wednesday, O’Donnell opened with a greeting directed specifically at anyone tuned in from 1600 Pennsylvania Avenue, then announced she had “some bad news” for President Petty Roosevelt — before adding, “That’s all I’m gonna say about you tonight, sweetheart.”
The move encapsulated her approach across the week: pointed, theatrical, and clearly calibrated to land on the ears of one specific viewer.
O’Donnell was among the latest in a string of guest hosts to handle the desk in Kimmel’s absence, following comedian Tiffany Haddish, actor and writer Ike Barinholtz, and actor Colman Domingo. O’Donnell said she was glad Kimmel extended the invitation, and praised him for what she described as his tenacity and strength. “Jimmy Kimmel Live!” airs weeknights at 11:35 p.m. ET on ABC.
