Rosie O'Donnell joke about Trump and aide draws gasps

Rosie O'Donnell, guest hosting "Jimmy Kimmel Live!", delivered a pointed joke about President Donald Trump's relationship with a senior White House aide during her monologue on Wednesday, August 19, 2026. The comment targeted 80-year-old Trump and his 35-year-old executive assistant, Natalie Harp, drawing audible reactions from the studio audience.

In her third night filling in for the show's regular host, O'Donnell began her monologue by saying, "A special hello to those of you watching from home and from the White House." She then added, "But I do have some bad news for President Petty Roosevelt. That's all I'm going to say about you tonight, sweetheart. You got to realize it's time to hang up your wig and let Natalie tuck you in." The remark prompted gasps and applause. "Time to go nighty night," she concluded.

The joke referenced increasing scrutiny of Harp's role and proximity to the president. Recent reports have described Harp as an omnipresent aide who trails Trump around the country. Her relationship with the president has been a subject of public commentary, including from Democratic Senator Jon Ossoff of Georgia, who recently quipped that Trump "wants to build his...