Rosie O'Donnell sings scathing anti‑Trump song on Jimmy Kimmel Live

comedyAug 22, 2026211,271

On her final night guest-hosting Jimmy Kimmel Live on August 22, 2026, Rosie O'Donnell closed the show by performing a scathing song aimed at Donald Trump, mocking him as "Donny Boy" and urging him to resign with lines including "you'll never be Obama, why not resign and make this country great again." The performance was widely shared online and covered in headlines, with The New York Times noting it capped O'Donnell's late-night stint and Substack commentary framing the number as a pointed political roast. Clips and writeups highlighted O'Donnell's direct taunts and comedic barbs, including references to Trump's critics and past fights with the comedian. Commentators and opinion pieces framed the ditty as both a comic send-off and a deliberate political jab at the former president. The segment prompted further coverage and clip circulation across news outlets and social links the same night.

Raymond Green

@wokeisalive.bsky.social

Trump has always hated @Rosie because Rosie O'Donnell always saw right through him. This video is from @TheView in 2006 (over 20 years ago!).

85145d ago

Ross Bezelthaur21

People weren’t ready to hear the truth back then. I think for a lot of people, they just saw the suit and the private jet and thought that people like Rosie were jealous of his success It’s only now people see he had no success whatsoever

Serafina13

Narcissists HATE people who can’t be conned. She saw right through him and he couldn’t stand it.

Barbara Garrett13

I knew in the 80's. The man is trash.

DetroitLionsFan11

You gotta love Rosie for calling him out back then, and doing it again now!!

Lydia Medina8

This is why he hates her she was the only one at that time to call him out

Bernadette DeMesme-Anders7

Trump’s buffoonery was not a secret. He was never the big man he portrayed on The Apprentice.

Quoting this

TrueTeller8

bsky.app/profile/woke... She's very well documented on Trump

Ace Hoffman5

Rosie knows Donald and always has...

angrygrrrl and F*cking B!tch2

OMG! This is perfection. Hellooooo MAGA-merica, New Yorkers have been trying to tell you this for the last 20 years!!!

Mark Ebenhoch aka INGLORIOUS BASTARD2

Rosie needs to run. Just to piss him off enough to force a mitochondrial infarction.

DocBray Is Thinking About Clouds2

"Donald, sit and spin my friend" is a classic lol

Dean Obeidallah

@deanobeidallah.bsky.social

Rosie O’Donnell just caused Trump’s worst nightmare to come to life! Rosie used her guest hosting gig on Jimmy Kimmel's show to comically destroy Trump. She even sang a song about Trump that went viral! We need more of Rosie! My article deanobeidallah.substack.com/p/rosie-odon...

17145d ago

Thom Hartmann

@hartmannreport.com

Saturday Report 8/22/26 — Rosie O’Donnell Delivers One Final FU to Trump and Sings Him Right Out the Door... The Best of the Rest of the News and Opinion… hartmannreport.com/p/saturday-r...

7445d ago

hear-ye--hear-ye.bsky.social1

If you impeach them. They lose they're retirements, security detail & medical benefits. They lose access to congress for future jobs. They lose they're connections to the tax payers funds. They all need to be impeach, so they cannot retire in peace.

Hala Ayala

@halaayala.bsky.social

Rosie O'Donnell just turned Danny Boy into a congressional hearing with a soundtrack. 💀 "Since we all know you'll never be Obama,why not resign and make this country great again?" Baby,when the Irish lullaby starts sounding like a transition memo, it's time to pack it up! 🤣 Keep roasting Rosie! 👏🏽

2945d ago

Our Common Defense

@ourcommondefense.bsky.social

Rosie O’Donnell should always guest host, under the guest name Rosie Oh Donald's in the Epstein Files

2645d ago

Joël.V

@tinyspotbigworld.bsky.social

"Since we all know you'll never be Obama. Why not resign and make this country great again? Yes We all know you'll never be Obama. Come on, resign and make this country great again!” Rosie O’Donnell on the Jimmy Kimmel show. As a Canadian I approve this for America 🇺🇸!

2145d ago

Bad Choices Make Good Stories

@badchoices.us

Rosie O'Donnell mocks Trump on Jimmy Kimmel Live: "Oh Donny boy" 😂

1144d ago

Joe Flynn

@chinajoeflynn.bsky.social

Psalm 55:4 "And say ye unto the Lord 'Rosie O'Donnell is a fat loser who was very mean to our president - extremely nasty woman - and must be punished by thine divine might.'"

1545d ago

Andys Theory 🦋⚡️💎

@andystheory.bsky.social

Rosie O’Donnell sings her song, Donnie Boy on Jimmy Kimmel. Enjoy😂😂 www.facebook.com/share/v/17wn...

945d ago

DrMary

@drshowup.bsky.social

Rosie O’Donnell Ends Late Night Stint With a Ditty to ‘Donny Boy’ www.nytimes.com/2026/08/21/a...

545d ago

Marcy Gall

@marcygall.bsky.social

Good for a laugh on another day of demented don’s madness www.thedailybeast.com/obsessed/ros...

845d ago

Rusty

@rusty-baxter.bsky.social

His reflecting pool is green as Mountain Dew! Thank you Rosie O’Donnell!

1045d ago

Sane Lunatic

@sanelunatic.bsky.social

Truly Freudian. But it's not as funny as it would be if he weren't - as Rosie O'Donnell said this week - Secretary of the Department of Health and Human Sacrifice.

545d ago

Trish 🇨🇦 Sorry! 🍁

@trishly.bsky.social

Beautiful ending to Rosie O'Donnell's time filling in for Jimmy Kimmel youtu.be/59St41a2TRE?...

544d ago

Melvin 🍁the 🍊💩hating cat -💙🦋🐧-my human is not a fan either . 🇨🇦💙🦋

@vespavixen.bsky.social

In this Mango Mussolini vs. Rosie O’Donnell world we live in - I’m proud to be Team Rosie.

845d ago

3 sources

open.substack.comSaturday Report 8/22/26 — Rosie O’Donnell Delivers One Final FU to Trump and Sings Him Right Out the Door...ew.comRosie O’Donnell slams Donald Trump with scathing song on last Jimmy Kimmel show: ‘You’ll never be Obama’hartmannreport.comSaturday Report 8/22/26 — Rosie O’Donnell Delivers One Final FU to Trump and Sings Him Right Out the Door...

Rosie O'Donnell sings scathing anti‑Trump song on Jimmy Kimmel Livecomedy

Rosie O'Donnell sings scathing anti‑Trump song on Jimmy Kimmel Live

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