Comedian Rosie O’Donnell used her second night guest-hosting “Jimmy Kimmel Live!” on Wednesday, August 19, 2026, to mock President Donald Trump’s recent embarrassing exit from Air Force One—hidden inside a catering cart—while making it abundantly clear she knew he was tuning in.
The 64-year-old entertainer didn’t hold back, addressing the audience before sarcastically thanking the 80-year-old commander-in-chief for boosting her profile. “I’m back in the spotlight, all thanks to President Oompa J. Loompa, who is watching us this evening from inside a catering cart,” she said. She finished by saying, “You know, I couldn’t have done it without you, sweetie. You brought me back, just like you did with fascism and the measles.”
Two Decades of Public Animosity
O’Donnell and Trump have maintained a bitter public rivalry since 2006, when the television personality was a co-host on “The View.” Their animosity has only intensified following his return to office. Trump has repeatedly attacked O’Donnell at rallies and shared demeaning AI-generated videos of her on Truth Social. In July 2025, he posted a doctored image of her and threatened to revoke her citizenship. O’Donnell responded on Instagram, telling him that 18 years on, she still occupied space rent-free in his “collapsing brain.”
That long-running grudge match provided context for her debut hosting stint. During her first monologue, O’Donnell focused entirely on her move to Ireland after Trump won the 2024 election—and never spoke his name. She explained that after reading Project 2025, she decided to leave America for “a place where people are driven to drink regardless of who’s running their country.” O’Donnell recalled how her child told classmates the family was being “forced to move to another country because the president of the United States hates my mother.” She concluded with a dig: “You know, right now he’s in the White House crying because I haven’t mentioned him.”
The Escape That Sparked National Ridicule
O’Donnell’s catering cart joke referenced an incident that became a source of widespread mockery for the administration. Last month, Trump traveled to Turkey for a NATO summit with other world leaders. During his departure, the Secret Service concealed him inside a catering vehicle—the kind used to transport food and supplies onto planes—then transferred him to a different aircraft before his return flight. The operation was carried out due to an alleged Iranian plot to target Air Force One. While the maneuver worked and remained secret for weeks, the story eventually leaked and has been ridiculed ever since.
Her decision to exploit that embarrassment for material on just her second night highlighted exactly why late-night insiders had eagerly awaited her appearance. Late-night host Jimmy Kimmel announced O’Donnell’s summer guest-hosting slot in late June during his season finale, calling it a “special treat for our commander-in-chief”—a remark that left little doubt about his motivation.
An Unexpected Opportunity
The invitation surprised O’Donnell, particularly given her own history with Kimmel, with whom she had previously clashed. She told Variety she was shocked when the offer arrived, noting she had never even been a regular guest on his program. She agreed only after confirming Kimmel genuinely wanted her involvement. In an interview with journalist Kara Swisher, O’Donnell said she intended to respect both Kimmel’s writers and his show’s reputation by taking the job seriously.
The Hollywood Reporter praised her disciplined approach, noting she avoided appearing obsessed with the president during her monologues. Instead of centering grievance, she centered her narrative: two years living quietly in Ireland, away from American media, before this high-profile television return. The paradox—that Trump’s obsessive focus on O’Donnell had gifted her a network stage—was evident to both performer and viewers.
More to Come
O’Donnell still has two nights remaining in her hosting rotation. Her opening night drew attention for its measured tone; her second-night monologue, built around the catering cart visual, demonstrated she would seize fresh ammunition when the news provided it. Whether she will speak Trump’s name before her run ends remains, by deliberate choice, uncertain.
