Jimmy Kimmel made Donald Trump the punchline when he announced that Rosie O’Donnell would guest host Jimmy Kimmel Live! during his summer break. O’Donnell’s August appearances then brought the long-running Trump feud back into view—but her first-night monologue focused mostly on her life in Ireland, while the next night featured more pointed jokes.
What Jimmy Kimmel said about Rosie O’Donnell’s guest-hosting booking
On June 18, 2026, Kimmel announced a voluntary two-month break and introduced the guest hosts who would fill in. He framed O’Donnell’s booking as a joke aimed at Trump, calling her one of the president’s “all-time favorites” and promising a “special treat.” He also addressed Trump directly: “And all I ask in return, Mr. President, is that you don’t do anything stupid while I’m gone.” TheWrap reported the announcement and its context.
That was a comic booking announcement, not an extended statement by Kimmel about the feud or a formal attempt to intervene in it. O’Donnell’s guest-hosting week followed about two months later.
What Rosie O’Donnell said on her first night
O’Donnell’s first episode aired August 17. The Washington Post reported that she spent much of her opening monologue talking about her life in Ireland and her move from the United States, rather than making Trump its main subject. She joked, “I’m being forced to move to another country because the president hates my mother. But in all fairness, I believe my mother hates him more.”
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Near the end of her Trump references, she waved toward the camera and said, “Hi,” followed by, “I know you’re watching.” The paper described the references as brief compared with the expectation that her debut would focus heavily on the president. The Washington Post’s account of the August 17 monologue also places the jokes in the context of her move and the public feud.
How the second-night monologue differed
On August 18, O’Donnell took a more directly sarcastic approach. TV Insider reported that she thanked Trump for bringing her back into the spotlight, saying, “I’m so grateful to be filling in for Jimmy and to be hosting a talk show on network TV once again,” and used nicknames including “Oompa J. Loompa” and “Velveeto Corleone.” These were jokes from the second-night monologue, not the first episode. TV Insider covered the August 18 remarks.
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An official Jimmy Kimmel Live! video listing published August 19 described an episode segment as O’Donnell sending Trump a message. The official listing also names other episode material.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Why Trump and O’Donnell have feuded publicly
The Washington Post traces the public dispute to O’Donnell’s 2006 appearance on The View, when she criticized Trump over his response to a Miss USA controversy and his business dealings. The paper reports that Trump continued mocking her over the years and more recently called for her citizenship to be revoked.
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O’Donnell has offered her own retrospective explanation. In a 2025 interview quoted by TV Insider, she said Trump had “had it out” for her for 20 years after she “told the truth about him on a program called The View.” That is O’Donnell’s characterization of the dispute, rather than an independently established start date.
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The difference between Kimmel’s joke and O’Donnell’s response
| Moment | Speaker and timing | What it was |
|---|---|---|
| Guest-host announcement | Jimmy Kimmel, June 18, 2026 | A brief joke about booking O’Donnell as a “special treat” for Trump during Kimmel’s summer break. |
| First guest-host monologue | Rosie O’Donnell, August 17, 2026 | A monologue focused mainly on Ireland and her move, with a few remarks directed at Trump. |
| Second guest-host monologue | Rosie O’Donnell, August 18, 2026 | A more pointed set of jokes, including sarcastic thanks to Trump for her return to network television. |
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