Comedian Rosie O’Donnell used her Aug. 18, 2026, appearance as guest host of “Jimmy Kimmel Live!” to ridicule President Donald Trump over his Secret Service-orchestrated exit from Air Force One hidden inside a catering vehicle — an incident that has haunted the administration since the story broke.
The 64-year-old entertainer opened her second evening in the host’s chair by addressing the 80-year-old commander in chief directly, thanking him with biting sarcasm for her return to television prominence. “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 to the studio audience. “You know, I couldn’t have done it without you, sweetie. You brought me back, just like you did with fascism and the measles.”
Ireland Exit and the First Night’s Restraint
O’Donnell’s debut monologue the previous night had taken a different approach, centering on her decision to move to Ireland following Trump’s 2024 election win rather than attacking the president by name. She described reading Project 2025 and determining she had to flee the country, eventually settling in a nation she characterized as “a place where people are driven to drink regardless of who’s running their country.” She recalled her child telling schoolmates the family was being “forced to move to another country because the president of the United States hates my mother.” The segment concluded with O’Donnell noting, “You know, right now he’s in the White House crying because I haven’t mentioned him.”
The Hollywood Reporter praised that first-night restraint as a refreshing departure from what could have been a grievance-fueled performance, highlighting how O’Donnell focused instead on her two years living outside the American media spotlight before this network television comeback.
The NATO Summit Escape That Became National Mockery
The catering cart joke resonated because the actual events had already humiliated the White House. In July, Trump attended a NATO summit in Ankara, Turkey, with fellow world leaders, and upon departure on July 8, the Secret Service concealed him inside a catering vehicle — the kind normally used for loading aircraft with food and supplies — before transferring him to a separate plane for his journey home. Officials cited an alleged Iranian plot targeting Air Force One. The administration kept the operation under wraps for weeks, but once the details emerged, the episode became fodder for widespread ridicule.
Late-night host Jimmy Kimmel announced in late June, during his season finale, that O’Donnell would be part of his summer guest-host lineup, describing the choice as a “special treat for our commander in chief” — a remark that made his intent unmistakable.
Nearly 20 Years of Public Hostility
The enmity between the television personality and the president dates to 2006, when O’Donnell was a co-host on “The View.” That initial clash evolved into one of the longest-running feuds in celebrity-political culture. Trump has repeatedly attacked O’Donnell at rallies and on his Truth Social platform, posting AI-manipulated videos mocking her. In July 2025, he posted a heavily doctored photograph and threatened to revoke her citizenship. O’Donnell responded on Instagram, telling him that after 18 years, she still occupied what she called his “collapsing brain” without paying rent.
An Unexpected Booking
The invitation itself came as a surprise, given that O’Donnell and Kimmel had themselves clashed earlier in their careers. O’Donnell told Variety the offer caught her off guard, noting that she had never even been a regular guest on the program. She said she accepted only after confirming Kimmel truly wanted her in the role. In an interview with journalist Kara Swisher, she explained that she planned to respect Kimmel’s writers and his show’s legacy by taking the assignment seriously.
The irony of Trump’s obsessive attention ultimately delivering O’Donnell a prime-time platform was evident to both her and viewers throughout her appearances.
O’Donnell’s opening-night monologue drew praise for its measured tone; her second night demonstrated a readiness to attack when handed timely material. In her remaining nights as host, she became notably more feisty, with the heavy applause of the studio audience.
