Jimmy Kimmel is temporarily handing over the reins of his late-night show to one of the people President Donald Trump hates most.
Kimmel announced during his Thursday monologue that he’ll be going on a two-month summer break, as he does every year. Jimmy Kimmel Live! will continue without him with a string of guest hosts, including returning hosts like Anthony Anderson and Jelly Roll.
Kimmel also announced one guest host who is sure to get Trump’s attention:
“As a special treat for our commander-in-chief, I asked one of his all-time favorites, Rosie O’Donnell, to be here,” Kimmel said.
“And all I ask in return, Mr. President, is that you don’t do anything stupid while I’m gone,” Kimmel joked.
O’Donnell is a talk show host, comedian, and actress who has been critical of Trump long before his 2016 run for president.
When she was a co-host on The View in 2006, O’Donnell called out Trump as “one of those snake-oil salesman” and mocked his treatment of women over the years.
“Left the first wife, had an affair, left the second wife, had an affair. Had kids both times,” O’Donnell said, quipping, “But he’s the moral compass for 20-year-olds in America.”
Trump has since repeatedly trashed O’Donnell for her appearance, even after he was elected president.
In September 2025, Trump posted on Truth Social a severely edited image of O’Donnell, writing, “We are giving serious thought to taking away Rosie O’Donnell’s citizenship. She is not a Great American and is, in my opinion, incapable of being so!”
O’Donnell has never stayed quiet on Trump. In early June she called the president a “psychopath” and argued that he had always been that way.
“If you grew up in New York, you knew he was an a-----e and a liar from day one,“ she told Variety. ”I remember when his planes were repossessed off the runways at LaGuardia. I remember when he was broke. I remember when he would call up places and pretend to be his own publicist."
O’Donnell had also reportedly complained about the Trump administration’s apparent role in getting Jimmy Kimmel Live! briefly pulled from air in September. Kimmel himself referenced the controversy when he announced his upcoming break.
“I will be taking the next two months off,” Kimmel said, adding, “This time voluntarily.”
