President Donald Trump’s long-running feud with Rosie O’Donnell is back in the national spotlight after Jimmy Kimmel handed his late-night show to one of the president’s most outspoken celebrity critics.
O’Donnell made her debut as guest host of “Jimmy Kimmel Live!” while Kimmel is away on summer vacation, and the comedian wasted little time addressing the political rivalry that has followed her for roughly two decades.
The decision to put O’Donnell behind Kimmel’s desk was almost guaranteed to attract attention. Trump has repeatedly criticized both entertainers, while Kimmel and O’Donnell have frequently used their public platforms to criticize the president.
Now those political and entertainment worlds have collided once again.
Rosie O’Donnell Targets Trump on Jimmy Kimmel’s Show
O’Donnell opened her appearance by acknowledging Trump’s longstanding criticism of “Jimmy Kimmel Live!”
She warned viewers to “buckle up” after joking that the president already disliked the program when Kimmel himself was hosting it.
The comment set the stage for several references to Trump throughout the evening, although O’Donnell largely avoided using the president’s name directly.
She eventually discussed her decision to move to Ireland following Trump’s victory in the 2024 presidential election.
O’Donnell said concerns about the country’s political direction influenced her decision to leave the United States. While discussing the move, she referred to Trump using a mocking nickname.
Her comments continued a feud that began years before Trump first entered the White House.
O’Donnell Sends Trump a Message
One of the most attention-grabbing moments came when O’Donnell discussed how her child explained the family’s move overseas to classmates.
According to O’Donnell, her child joked that the family had to leave because the president disliked her mother — before adding that O’Donnell probably disliked Trump even more.
O’Donnell then looked directly into the television camera.
“Hi, I know you’re watching,” she said.
It was a brief comment, but one clearly aimed at the president.
The exchange demonstrated why Kimmel’s selection of O’Donnell as a guest host immediately attracted political attention. Few entertainers have maintained such a lengthy and public feud with Trump.
Conservative Critic Responds to O’Donnell
O’Donnell’s appearance quickly drew criticism from conservative media.
Curtis Houck, managing editor of NewsBusters at the Media Research Center, criticized O’Donnell’s continued focus on politics and questioned her portrayal of life under the Trump administration.
Houck argued that O’Donnell remains free to return to American television, criticize the president and continue earning a living despite her warnings about Trump.
His response pointed to a larger disagreement that has surrounded political entertainment for years.
Conservative viewers have frequently complained that late-night television has moved away from broadly appealing comedy and increasingly embraced liberal political commentary.
Kimmel has become one of Trump’s most prominent critics in late-night television, and inviting O’Donnell to temporarily take control of his program is likely to deepen that perception among viewers on the right.
O’Donnell Explains Her Move to Ireland
O’Donnell also spent a significant portion of the program talking about her new life in Ireland.
She praised the reception she has received from local residents and described the country as a source of comfort since leaving the United States.
According to O’Donnell, people have approached her in public to welcome her and tell her that she belongs there.
She described Ireland as both a “refuge” and a “salvation.”
Her decision to move became political news because O’Donnell publicly connected her departure to Trump’s return to power.
Despite relocating overseas, however, she has remained involved in American political and cultural debates — and her temporary return to late-night television has once again placed her directly in the middle of one.
Emotional Moment Changes the Tone
Not everything about O’Donnell’s appearance centered on politics.
The comedian became emotional while paying tribute to actress Hayden Panettiere, who died Sunday at the age of 36.
Panettiere had appeared on “The Rosie O’Donnell Show” during her career, giving the tribute a personal connection for O’Donnell.
The emotional moment provided a sharp contrast to the political jokes and personal stories that dominated other portions of the broadcast.
O’Donnell Takes One More Shot at Trump
Toward the end of her monologue, O’Donnell returned to the president one more time.
After largely avoiding saying Trump’s name throughout the program, she joked that he was probably sitting in the White House upset because she had not given him enough attention.
The remark soon received a response.
Trump took to Truth Social and shared a cartoon portraying O’Donnell repeatedly thinking about him.
“She (?) is obsessed!” Trump wrote.
The president’s response immediately added another chapter to a celebrity feud that has survived for approximately two decades.
It also demonstrated how quickly late-night entertainment can spill over into national political discussion.
Why Jimmy Kimmel’s Decision Matters
O’Donnell previously acknowledged that she was surprised Kimmel offered her the guest-hosting assignment.
The two entertainers have not always been close, and O’Donnell has described their past relationship as adversarial.
Nevertheless, she said she appreciated the opportunity and praised Kimmel for speaking openly about political issues.
O’Donnell also framed political criticism from entertainers as a matter of free expression, arguing that Americans have a constitutional right to speak against their government.
That argument is unlikely to settle the broader debate over late-night television.
Critics contend that programs once built around comedy, celebrity interviews and entertainment have become increasingly partisan. Supporters argue that comedians have every right to use their programs to address political issues.
For conservative Americans who have watched Hollywood become increasingly political, O’Donnell’s appearance could reinforce concerns about liberal politics dominating mainstream entertainment.
Trump and O’Donnell’s Feud Goes Back Decades
The latest exchange is hardly the beginning of the Trump-O’Donnell rivalry.
Their public feud stretches back to the 2000s, long before Trump became president.
Over the years, the two have exchanged harsh criticism through television appearances, interviews, political campaigns and social media.
Trump’s rise in Republican politics only intensified the dispute.
O’Donnell became one of his most vocal celebrity opponents, while Trump repeatedly responded to her criticism.
That history made Kimmel’s choice particularly noteworthy.
By giving O’Donnell control of “Jimmy Kimmel Live!” for several nights, Kimmel placed one of Trump’s most recognizable entertainment-world adversaries behind the desk of a program that Trump has already criticized repeatedly.
Late-Night Television’s Political Divide
The episode also highlights a much larger cultural question.
Should late-night television primarily entertain Americans, or should hosts use their programs to promote political opinions and criticize elected leaders?
For decades, political jokes have been part of American comedy. But critics argue that modern late-night programs have increasingly moved beyond jokes and into partisan advocacy.
That shift has frustrated some viewers, particularly conservatives who believe their political views are regularly treated as punchlines by Hollywood entertainers.
Others maintain that political satire has always been an important part of American culture and that comedians should be free to criticize presidents from either party.
Whatever viewers believe, the Trump-O’Donnell showdown demonstrates that the intersection of politics and entertainment is not disappearing anytime soon.
Trump Gets the Last Word — For Now
Kimmel may be away from his show, but his decision to put O’Donnell behind the desk has generated plenty of attention without him.
O’Donnell used the opportunity to revisit her concerns about Trump, discuss why she left the United States and directly tease the president from national television.
Trump responded in characteristic fashion through social media.
For longtime followers of their rivalry, the exchange probably felt familiar.
But with Trump back in the White House and O’Donnell once again appearing on a major American television program, their decades-old feud has suddenly found a new audience.
And with O’Donnell scheduled to continue guest-hosting this week, the latest Trump-versus-late-night battle may not be over yet.
What do you think? Has late-night television become too political, or should comedians be free to take on the president?