Rosie O’Donnell has returned to the late-night airwaves, stepping into the guest host chair for Jimmy Kimmel Live! throughout this week. During her initial monologues, the comedian directed pointed commentary at President Donald Trump, a figure she has clashed with publicly for two decades.
This week marks O’Donnell’s first return to a television desk in nearly thirty years. During the broadcast, she opted to reference the president using monikers such as Oompa J. Loompa and Velvito Corleone rather than his formal name. The White House responded to these segments through spokesperson Davis Ingle, who labeled O’Donnell a nasty woman and suggested she suffers from Trump Derangement Syndrome.
The history between the two individuals traces back to 2006 during O’Donnell’s tenure on The View, when she openly questioned Trump’s business practices regarding the Miss USA pageant. The tension persisted for years, eventually prompting O’Donnell to relocate to Ireland in 2025 as the political environment in the United States intensified. According to O’Donnell, living abroad has provided her with a sense of personal recovery from the constant cycle of news cycles involving the White House.
Despite her distance, the feud remains active. In July, the president circulated an AI-generated video that depicted himself as a doctor treating O’Donnell and other celebrities for what he characterizes as an irrational fixation on his administration. O’Donnell subsequently characterized the president as a highly negative influence on the country during a recent media interview.
This guest hosting stint highlights the persistent friction between high-profile cultural figures and the current administration. While Kimmel remains on a summer break, O’Donnell’s presence on the program ensures the ongoing rivalry continues to find space in the mainstream media landscape.