O’Donnell’s first turn behind Kimmel’s desk centered on a direct camera message, Ireland jokes and a public Trump feud that began in 2006.
Rosie O’Donnell made her debut as a guest host on Jimmy Kimmel Live! while Jimmy Kimmel was away, and she used the opening monologue to address Donald Trump directly. According to reports on the broadcast, her message to Trump was blunt but comic: “Hi, I know you’re watching.”
She followed that with a reminder that the president had disliked the show even when Kimmel himself hosted it. The appearance gave O’Donnell a network late-night platform for jokes about Trump, her move to Ireland and a public feud that has continued for years.
A message aimed at an old adversary
O’Donnell did not need to say Trump’s name repeatedly to make the target clear. According to The Daily Beast’s report on her monologue, she opened by speaking toward the camera: “Hi, I know you’re watching.”
She then connected her own long-running conflict with Trump to his history with Kimmel. “The President hated Jimmy Kimmel Live! when it was hosted by Jimmy Kimmel,” O’Donnell told the audience, adding, “Buckle up, people.”
The line worked as both a jab and a framing device. O’Donnell was taking the chair of another entertainer Trump has publicly criticized, and she made that context part of the monologue.
Near the end of the monologue, she reportedly offered another pointed aside: Trump was “in the White House crying because I haven’t mentioned him.” The joke rested on a contrast that ran through the set. Even when Trump was not named, his presence was part of the story O’Donnell was telling.
Ireland became part of the set
The Daily Beast reported that much of O’Donnell’s monologue focused on Ireland, where she has said she relocated following Trump’s 2024 election victory. She described reading Project 2025 and deciding she needed to leave the United States.
Her explanation was delivered in the style of a stand-up bit rather than a policy speech. She joked that Ireland is a place where people are “driven to drink regardless of who’s running their country,” using the move as material while underscoring that the decision carried personal weight.
O’Donnell also recounted how one of her children explained the family’s departure to classmates. The anecdote turned the public conflict into a family-level story, though it was presented with the punchline and exaggeration expected in a late-night monologue.
That balance shaped the appearance’s tone. O’Donnell’s comments were political, but the set was not built as a formal argument about an administration. It was an entertainment performance in which personal upheaval, resentment and absurdity were converted into jokes.
The feud dates back to 2006
O’Donnell and Trump’s public clash dates back to 2006, when she criticized him during a segment on The View, according to People. Trump responded at the time in an interview with the magazine, and the exchange became the start of a dispute that has continued through television appearances, interviews and social-media posts.
Reporting on O’Donnell’s guest-host debut noted that Trump has continued to insult her publicly and has mocked her move to Ireland. In July 2025, he threatened to revoke her U.S. citizenship.
O’Donnell answered that threat in an Instagram post, attacking Trump in personal and political terms. Her response made clear that she did not view his comments as harmless celebrity sparring, and that perspective carried into her Kimmel monologue.
On Kimmel’s stage, the old dispute was not background trivia. It was part of the premise: a comedian who has been publicly criticized by Trump was filling in for another late-night host who has also drawn Trump’s ire.
A surprising turn behind Kimmel’s desk
O’Donnell has said she was surprised to be asked to fill in for Kimmel. In comments reported by Variety, she recalled telling her publicist that she had not even previously appeared as a guest on the show.
She also said she and Kimmel had once been “adversarial,” which made the invitation more notable than a standard summer-host announcement. The booking brought together past friction with a shared place in Trump’s public criticism of entertainers.
Kimmel reportedly previewed O’Donnell’s role at the end of the season by calling it a “special treat for our commander-in-chief.” That framing made the booking openly pointed before O’Donnell reached the monologue.
O’Donnell’s first night then delivered on that setup. She spoke to Trump through the camera, joked about the show he had already criticized and turned her Ireland move into part of the late-night story.
What remains unclear
There is still a limit to what one monologue can establish. It is unclear whether Trump will respond publicly, whether O’Donnell’s guest-hosting run will keep returning to him, or whether the first-night message will remain the defining moment.
What is clear is that O’Donnell did not treat her Kimmel debut as an occasion to soften a dispute that has become central to her public persona. Her first night hosting Jimmy Kimmel Live! made the basic point quickly: she knows Trump may be watching, and she is not interested in avoiding the subject.
Her warning was less a prediction of a specific consequence than a signal of intent. “Buckle up” told viewers that the comedian’s return to late-night television would connect the personal, the political and the punchline.
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