Rosie O’Donnell Roasts Trump on Kimmel, Reigniting Old Feud
Rosie O’Donnell’s return to late-night television has brought a decades-old feud with Donald Trump roaring back into the spotlight. Taking the guest host reins on “Jimmy Kimmel Live!” this week, O’Donnell didn’t hold back, launching a series of pointed jabs at the former president during her opening monologue on Monday night. Kimmel is currently on his summer break, and O’Donnell, a veteran comedian and former talk show host, is filling in.
A Familiar Target
O’Donnell kicked off her hosting gig by acknowledging Trump’s well-known dislike for “Jimmy Kimmel Live!,” quipping to the audience, “The President hated Jimmy Kimmel Live! when it was hosted by Jimmy Kimmel. Buckle up, people.” This set the stage for a monologue that frequently circled back to her long-standing public animosity towards Trump.
The comedian, who made a significant life change by relocating to Ireland in January 2025, attributed her move partly to the political climate following Trump’s 2024 election victory. During her monologue, she referred to the former president with the colorful moniker “Mango Mussolini.” She explained her decision to move, citing concerns about the future outlined in initiatives like Project 2025. “I read that Project 2025 and said, ‘Got to get myself out of here, you know,’” O’Donnell shared, adding with a touch of dark humor about her new home, “and I decided to go to Ireland, a place where people are driven to drink regardless of who’s running their country.”
O’Donnell recounted a poignant moment when her child informed classmates about their impending move abroad. According to O’Donnell, her child explained, “‘I’m very sorry. I won’t be able to graduate sixth grade with you. I’m being forced to move to another country because the president of the United States hates my mother. But in all fairness, I believe my mother hates him more.’”
In a direct address to the camera, seemingly aimed at Trump himself, O’Donnell smiled and said, “Hi, I know you’re watching.” This personal dig underscored the deep personal nature of their protracted public dispute.
Reactions and Reflections
O’Donnell’s political commentary and jabs at Trump did not go unnoticed. Curtis Houck, managing editor for NewsBusters at the Media Research Center, offered a critical perspective. “Rosie O’Donnell is painfully unfunny and the personification of letting politics run your life, with whoever is in power determining your happiness,” Houck stated. He further commented on O’Donnell’s media appearances leading up to her hosting gig, suggesting, “She’s still gainfully employed doing whatever it is she does to make money. It’s as if her shtick about Trump being an incapacitated-yet-menacing authoritarian is all an act to secure the eyeballs of the deranged left.”
During her time on the show, O’Donnell also spoke about her new life in Ireland, contrasting the welcoming nature of its people with her previous experiences in New York City. “[The people in Ireland] would stop me in the street. They would say to me, ‘Welcome, Rosie. You’re home. We love having you here,’” she recalled, describing the country as “my refuge and my salvation.”
The comedian also took a moment to pay a heartfelt tribute to Hayden Panettiere, a guest from her former show who passed away the previous day. O’Donnell appeared visibly emotional, stating tearfully, “I’m just heartbroken over the passing of Hayden Panettiere last night.”
A Lingering Jab
As her monologue concluded, O’Donnell delivered what seemed to be a final, subtle jab at the president, despite having largely avoided mentioning him by name throughout the rest of the show. With a knowing smile, she added, “You know, right now he’s in the White House crying because I haven’t mentioned him.”
The sentiment appeared to be mutual, as Trump responded via a post on Truth Social. He shared a cartoon depicting O’Donnell preoccupied with thoughts of him, accompanied by the caption, “She (?) is obsessed!”
An Unexpected Opportunity
O’Donnell had previously expressed surprise at receiving the guest-hosting offer from Kimmel, acknowledging their past “adversarial” relationship. In an interview with Variety, she conveyed her gratitude for the opportunity, stating, “I support [Kimmel] in what he’s doing with the First Amendment, and our ability as entertainers and citizens to speak out against our government that’s enshrined in the Founding Fathers’ writings about our government, so I think he’s fantastic.” She also drew a parallel to Stephen Colbert’s situation, wishing he had received similar support.
The dynamic between O’Donnell and Trump, a feud that has simmered for over two decades, continues to be a notable feature of the public discourse, with O’Donnell’s return to late-night television providing a fresh, albeit familiar, platform for their ongoing animosity.
