Rosie O’Donnell used her third stint as guest host on Jimmy Kimmel Live to take another swipe at Donald Trump, this time weaving in chatter surrounding his executive assistant, Natalie Harp.
O’Donnell, 64, opened Wednesday’s monologue by offering “a special hello to those of you watching from home.”
“And from the White House.”
“But I do have some bad news for President Petty Roosevelt: That’s all I’m going to say about you tonight, sweetheart,” she said, looking straight into the camera.
That promise, however, did not last long.
Moments later, O’Donnell delivered another joke aimed at the President, referencing recent reports that described the 35-year-old Harp’s intense loyalty to Trump as an “unhealthy obsession,” as well as renewed speculation over whether he has begun wearing a wig.
“You got to realize it’s time to hang up your wig and let Natalie tuck you in,” O’Donnell said, taking a final dig at Trump, 80.
“Time to go nighty night.”

‘You got to realize it’s time to hang up your wig and let Natalie tuck you in,’ Rosie O’Donnell told Donald Trump during her third Jimmy Kimmel Live monologue on Wednesday, leaning into recent rumors about his assistant

Natalie Harp (pictured right) once rode in the trunk of an SUV to go to court with Trump. The 35-year-old has been in the news since Georgia Senator Jon Ossoff brought her up in a Sunday speech bashing the President, leading to renewed speculation about their closeness
Harp has been a subject of many discussions since the start of the week, after Georgia Senator Jon Ossoff mentioned her in a speech.
Ossoff, while criticizing Trump, said the President simply ‘wants to build his ballroom and travel with Natalie on their apparently defenseless flying palace gifted by the Emir of Qatar’ on Sunday.
The mention already came amid growing questions about Trump’s closeness with the staffer, who has been dubbed the ‘human printer’ for a tendency to tail the President with a portable printer so he can read documents as hard copies, The New York Times noted in a profile on Tuesday.
The same day, CNN’s Erin Burnett had Harp’s estranged brother Preston Harp on her show ‘OutFront.’
He said his sister may have an ‘unhealthy obsession’ with the President after CNN reported she jumped into an SUV trunk just to accompany Trump to a New York federal court building in 2023.
As for the ‘wig’ remark, the President sported a new, fuller hairstyle in Las Vegas earlier this month, spawning an avalanche of memes suggesting it was a hairpiece.
White House Press Secretary Karoline Leavitt batted back the social media speculation, telling the Wall Street Journal: ‘Lighting is everything.’

O’Donnell’s made a remark about Trump’s ‘wig’, after he sported a new, fuller hairstyle in Las Vegas on August 5. Many on social media suggested it was a hairpiece. The President’s hairstyle has since returned to normal
The President’s hairstyle returned to normal after the appearance on August 5.
O’Donnell, meanwhile, relocated to Ireland last year with her 11-year-old non-binary child after Trump was reelected.
She told what would usually be Kimmel’s LA audience on Monday that ‘Jimmy ask[ed] if [she] was interested’ in guest-hosting.
‘So I dusted off my Koosh balls and here I am.’
Kimmel and Trump have been at odds for nearly a year since the latter called for the late night host’s show to be canceled over a crack Kimmel made about conservatives wanting to distance themselves from the suspected assassin of Charlie Kirk.
White House spokesperson Davis Ingle told Our News Outlet on Tuesday after O’Donnell touted the fact she was ‘back in the spotlight all thanks to President Oompa J. Loompa’: ‘Rosie O’Donnell is a nasty woman and a total slob whose brain has been completely destroyed by Trump Derangement Syndrome.’