Jimmy Kimmel announced on June 18, 2026, that he will step away from “Jimmy Kimmel Live!” for two months this summer — and he is handing the reins to a lineup that includes one figure almost certain to rattle the White House: Rosie O’Donnell, President Donald Trump’s most enduring celebrity adversary.
Kimmel delivered the announcement with a pointed aside about his involuntary absence last year. “I hope you’re paying attention this summer, because I will be taking the next two months off — this time voluntarily,” he told the audience, a clear nod to September 2025, when ABC pulled the program for nearly a week after he criticized some Republicans for their reaction to the death of conservative commentator Charlie Kirk.
A Guest Roster Built to Make Headlines
Kimmel named what he called “a potent group of hosts” who will begin substituting starting the week of July 6. Tiffany Haddish will kick things off during that first week, with Anthony Anderson, Ike Barinholtz, Colman Domingo and Jelly Roll taking turns throughout the summer. O’Donnell will also host, with her week confirmed to begin Monday, August 17 — and it’s sure to generate headlines. Kimmel described booking O’Donnell as a tongue-in-cheek present for the president, saying he had invited one of Trump’s favorite people to keep delivering memorable moments.
He drew laughter and applause from the studio crowd before joking that he hoped Trump wouldn’t make any rash decisions while he was gone — a line that worked both as humor and pointed commentary.
O’Donnell and Trump: Two Decades of Open Warfare
The feud between O’Donnell and Trump stretches back to 2006, when she criticized him during an episode of “The View.” What began as a sharp exchange on daytime television calcified over the years into something more corrosive, flaring with particular intensity after Trump’s re-election in 2024. O’Donnell relocated to Ireland with her youngest child in early 2025, shortly after that victory, stating she made the move to protect her child’s well-being and her own mental health amid the stress of Trump’s political presence and his public threats to revoke her U.S. citizenship.
Those threats were not rhetorical. In July 2025, Trump posted on Truth Social that he was “giving serious consideration to taking away” O’Donnell’s citizenship, calling her “a Threat to Humanity” who should remain in Ireland and closing with “GOD BLESS AMERICA.” That September, he shared a distorted image of her face on the same platform and renewed the citizenship threat in writing, stating the administration was “giving serious thought to taking away Rosie O’Donnell’s Citizenship” and declaring she was “not a Great American.”
O’Donnell responded on Instagram, calling Trump a “criminal con man” and posting a photo of Trump with Jeffrey Epstein, writing that he was “rattled” and that she was “everything you fear.”
The back-and-forth between the two continued to escalate through the fall, with neither side showing any sign of stepping back. The feud was still very much alive at the June 7, 2026 Tony Awards, where O’Donnell made a rare U.S. public appearance — her first major one since relocating to Ireland — and called Trump “a conman,” “a narcissist” and “a psychopath” in a red-carpet interview with Variety.
The Shadow of Last September’s Suspension
Kimmel’s reference to taking time off “voluntarily” carried real weight for anyone who followed the events of September 2025. His Sept. 15, 2025, broadcast, in which he criticized Republican responses to Charlie Kirk’s death, prompted swift condemnation from prominent conservative figures. Federal Communications Commission Chair Brendan Carr threatened regulatory action, and ABC pulled the show from the air. Protests erupted outside Walt Disney Studios in Burbank, California, and at ABC headquarters in New York, with viewers on both sides debating free speech and broadcast responsibility.
Kimmel returned to the air on Sept. 23, 2025, visibly shaken. He told his audience he had never intended to make light of a young man’s death and offered a defense of the very platform that had just silenced him, arguing that the show itself mattered far less than living in a country that permitted it to exist. That return episode drew more than six million total viewers.
Matt Damon Crashes the Farewell in a Trojan Horse
The June 18 send-off would not have been complete without a visit from Kimmel’s long-running on-air nemesis, Matt Damon. The actor — who arrived on the “Jimmy Kimmel Live!” stage inside a literal Trojan horse brought in by a UPS driver — told the audience he had come to promote Christopher Nolan’s “The Odyssey,” set to open July 17. The entrance was in keeping with the film’s ancient Greek subject matter, and the two men traded their usual insults before Damon’s promotional plug brought the bit to a close. The gag served as a fitting send-off: absurd, self-aware and built entirely around the kind of recurring bit that has defined the show’s identity for years.
With guest hosts spanning comedy, drama and music, “Jimmy Kimmel Live!” is set to maintain its nightly presence through the summer. Whether O’Donnell’s eventual appearance draws the presidential response Kimmel almost certainly anticipated when he booked her remains to be seen.