Jimmy Kimmel is going on vacation, and he is leaving Donald Trump a present the president did not ask for.
On Thursday’s “Jimmy Kimmel Live!”, the host told viewers he is taking the next two months off and handing the desk to a rotating cast of guest hosts. The name that drew the gasps was Rosie O’Donnell, the comedian and former “View” co-host who has feuded with Trump for the better part of two decades.
“As a special treat for our commander in chief, I asked one of his all-time favorites, Rosie O’Donnell, to be here to keep the hits coming,” Kimmel said, straight-faced. Then the kicker: And all I ask in return, Mr. President, is that you don’t do anything stupid while I’m gone.
“I will be taking the next two months off, this time voluntarily,” Kimmel told the audience before running through the lineup. He called it a “potent group of hosts,” a mix of stand-ups and actors: Tiffany Haddish, Colman Domingo, Ike Barinholtz, Anthony Anderson and the country-rap star Jelly Roll. The guest run begins the week of July 6 with Haddish, and O’Donnell’s week is slated for August, according to NBC News. Domingo and Barinholtz are first-timers behind the desk; Anderson is the show’s most frequent fill-in, with 24 turns to date.
A feud with a long paper trail
The casting is a joke with history. The bad blood dates to 2006, when O’Donnell criticized Trump on “The View” over his handling of the Miss USA pageant and he fired back in the press. It followed him into politics: at a 2015 Republican primary debate, pressed about his past language toward women, Trump cut in, “Only Rosie O’Donnell.”
It never really cooled. After Trump returned to the White House, O’Donnell moved to Ireland with her youngest child, citing the country’s direction and policies affecting transgender people. Trump floated revoking her U.S. citizenship, a threat legal scholars noted he has no power to carry out against someone born on American soil. She has rarely held back when asked about him in public.
Trump’s own summer has given comedians plenty to work with; he turned 80 last week with his approval rating stuck in the 30s.
For Kimmel, stepping away for the season is routine by now. This is the fifth summer he has done it, a habit he started in 2020 during the pandemic and repeated in 2021, 2022, 2024 and 2025. His 2023 break happened to fall during the writers’ and actors’ strikes that shut late-night down anyway.
The booking also lands at a moment when late-night trades as much on its politics as its punchlines, a long way from the era when network comedy leaned on the craft of sitcom veterans. Kimmel is expected back at his 11:35 p.m. post the day after Labor Day. Until then the chair belongs to other people, and at least one of them was picked specifically to get under the president’s skin.
