Donald Trump hates many, many things—as we hear daily from the whiner-in-chief. But the one thing Trump hates the most is what happened to him this week. And worse for him, it was done by a person he truly despises.
I’m talking about Rosie O’Donnell and her brutal comedic take down of Trump nightly as she guest hosted on Jimmy Kimmel’s late night TV show. O’Donnell hilariously mocked Trump from his whig to his horrible poll numbers—even singing a song parody about him that went viral. And the worst part for Trump is that it made headlines nationwide including on Fox News.
We have never seen an American president hate being mocked more than Trump. He is the only President never to attend a White House Correspondents’ Dinner when a comedian was the performer out of fear of being laughed at. Like all aspiring tyrants, Trump doesn’t want you laughing at him--he wants you fearing him.
But keep in mind Trump has long lashed out comedians for causing people to laugh at him. In fact, his feud with Rosie began back in 2006 when she mocked his combover, his cheating on his wife and more while a co-host on The View. That led to Trump for years calling her names such as “disgusting,” “nasty” and “a slob.” He even threatened to sue her.
And during the 2016 presidential debates, Trump on numerous occasions used that platform to go after O’Donnell. For example, in the presidential debate in September 2016 against Hillary Clinton, Trump stated: “Rosie O’Donnell, I said very tough things to her and I think everyone would agree that she deserves it and nobody feels sorry for her.”
That is why Rosie using the guest hosting gig on Kimmel—the very show Trump wanted cancelled—to comically filet Trump grabbed so much attention.
Rosie began her run on Monday with some mild jabs at Trump where she called him, “President Oompa J. Loompa.” She later joked that Trump’s attacks on her had made her “re-famous.” The award-winning comedian continued with this zinger: “Couldn’t have done it without you, sweetie. You brought me back, just like you did with fascism and the measles.”
But O’Donnell—who has been living in Ireland since Trump took office again in 2025—was just getting warmed up. On Wednesday, she joked, “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.” She then added, “That’s all I’m going to say about you tonight, sweetheart. Time to go nighty night.”
She then delivered a barb tied to the news of Trump spending so much time with his 35-year-old aide Natalie Harp with the line, “You got to realize it’s time to hang up your wig and let Natalie tuck you in.”
Boom! And come Thursday—her final night guest hosting—Rosie came out with her comedic guns blazing as she repeatedly targeted Trump all building to a song parody that has gone viral. She first thanked “everyone who’s been watching this week, especially the hungry, hungry hypocrite in the White House.” Adding this barb, “it’s kind of weird to think he spent more nights with me this week than Melania.”
Rosie then turned to Trump’s efforts to silence dissent. She stated--to huge applause—that everyone has “the right to free speech in this country, whether Orange Voldemort likes it or not.”
Then came the song. To the tune of the Irish classic “Danny Boy,” Rosie sang a parody that utterly destroyed Trump by hitting on real issues that drive him crazy. Some of the best lyrics of her song titled “Donny Boy,” included, “Poor Donny boy, your polls, your polls are falling,” she sang. “Your reflecting pool is green as Mountain Dew. Your wig’s a mess, your ballroom is appalling, and with Iran you’ve bit off more than you can chew. Measles are back, inflation is a-swelling; you post all night, you’re sleeping while you work. And what’s with all this useless crap you’re selling?”
Rosie then delivered these even more crushing lyrics: “Hey, sweetie pie, you’re driving us all berserk. But there’s a way to end this drama. It’s time to use that stable-genius brain. Since we all know you’ll never be Obama.”
That line alone got a huge applause. But this lyrical line was the showstopper: “Why not resign, and make this country great again?”
Down goes Trump! The crowd roared with laughter and cheers as Rosie repeated those last lines. You can watch the hilarious song parody below:
Any other President would have ignored Rosie’s appearance. That is any President other than “Oompa J. Loompa.” Trump was so angered by Rosie’s headline grabbing jokes at his expense, the White House issued a statement slamming the comedian, “Rosie O’Donnell is a nasty woman and a total slob whose brain has been completely destroyed by Trump Derangement Syndrome.” Ahh, all the class and decency we’ve come to expect from Donald Trump summed up in one line!
All of this is why Rosie brought Trump’s worst nightmare to life as the nation is laughing at him. Worse for Trump is that the ratings were great and Rosie’s monologues each night were racking up in the area of three million views each on YouTube.
The only thing that could make this better for us--and worse for Trump--is if Rosie hosted her own nightly show. Here’s hoping we see that!
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