Wednesday, August 19, 2026

Rosie O’Donnell Second Night of Kimmel: Calls Trump “President Oompa J Loompa,” Thanks Him for Bringing Her Back “Like Fascism and the Measles”

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Rosie O’Donnell’s second night guest hosting Jimmy Kimmel was a winner again.

Of course, she got a few zings at Donald Trump out of the way at the start of her monologue.

She said, “All of a sudden I’m re-famous, back in the spotlight all thanks to President Oompa J Loompa, who is watching us this evening from inside a catering cart. I couldn’t have done it without you, sweetie, it brought me back just like you did with fascism and then the measles.”

That bit got huge laughs from the rap studio audience.

Rosie’s main guest was Jean Smart, on her Emmy tour for “Hacks.” Smart, who’s been out campaigning day and night during this Emmy voting week, seemed a little tired but was endearing as ever. They discussed Smart’s five years playing fictional comic Deborah Vance. Smart said she’d been a big fan of Joan Rivers, but really loved Phyllis Diller.

A part of their multi-segment conversation was surprising, however. O’Donnell and Smart really put down the Met Gala, ensuring that both of them will be on Anna Wintour’s blacklist forever. Rosie said, during a discussion of dressing up for events, “I think what they should do for prisoners is send them to the Met Ball.” Smart concurred that she’d heard it was “torture.” It was very funny for the audience but it won’t be for Wintour if someone tells her about it.

O’Donnell, in her monologue, used some more of the material from her winning off Broadway show, “Common Knowledge,” talking about her 13 year old autistic child, Clay. And Rosie also featured a three year old girl named Leona she found on YouTube, who was shockingly beguiling singing “Let it Go” from “Frozen,” and showing off what may be perfect pitch.

What came across for the second night was that O’Donnell is a total star and professional. Even if she’s returning to Ireland for now, it’s pretty clear that Rosie could start a daytime talk show if she wants one once Trump is safely out of office. This Kimmel run is the best audition idea I’ve ever seen.

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Roger Friedman
Roger Friedman
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009, where he covered Michael Jackson, and previously wrote the "Intelligencer" column at New York magazine in the mid-1990s, where he covered the O.J. Simpson trial. He also edited Fame magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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