Posted August 24, 2026 | by KimS | in DemDaily, Donald Trump, Entertainment, Humor Round Up

DemDaily: A Little Political Humor! Our Monthly Roundup

August 24, 2026

To kick the week off and remind us to laugh!

With love from Rosie
Rosie O’Donnell kicked off hosting four nights of Jimmy Kimmel, with a greeting for President Trump: “Hi, I know you’re watching!”

“They said you can’t come home again, but here I am. And if you thought the president hated ‘Jimmy Kimmel Live’ when it was hosted by Jimmy Kimmel, buckle up, people. Buckle up!”

“You know, I’ve been living in Ireland for the past two years because of Mango Mussolini. I read that Project 2025 and said, got to get myself out of here, you know? And I decided to go to Ireland, a place where people are driven to drink regardless of who’s running their country.”

“And if you’re wondering why I’m here, it all started like a heist movie. [imitating a gangster] I was out of this talk show game. Living abroad. Then I got a secret message from Jimmy asking if I was interested in one last score. So I dusted off my Koosh balls and here I am.”

“I haven’t sat behind a desk on TV in almost 30 years, and a lot has changed since the ’90s. Well, back then, there was a war in the Middle East, climate change was ravaging our planet. We had a president who was embroiled in scandals. But today, everything is so chill.” - Rosie O’Donnell

Together Again
After posting a photo with North Korean leader Kim Jong-un last week, President trump said he expected to meet with Kim later this year. “Man, you know you’re depressed when you’re texting an old hookup from seven years ago.” – Jimmy Fallon

“Trump and Kim can meet in November. It all really depends on how their couples Halloween costume goes, so. [imitating Trump] ‘I’m chips; he’s guacamole.’” – Jimmy Fallon

“Here’s a photo from the last time Trump met with Kim Jong-un. And, yeah, I think it’s cute how their bellies bump like two soon-to-be moms at Lamaze class.” – Jimmy Fallon

On the new US Territory
“We also learned today that the United States could be acquiring some new land soon,” said Rosie O’Donnell. “Velveeto Corleone was up bright and early at 7am this morning to post an image of a map listing the Strait of Hormuz as a US territory, which makes literally no sense. I’ll put it this way: If the US is in charge of the strait, then I’m also straight — and let’s face it, I’m not.”

“Well, guys, according to a new poll, President Trump’s approval rating has fallen to 33%, the lowest level of his presidency. Yeah, I mean, most people like to drop a few for the summer, but this is pretty bad.” – Jimmy Fallon

“The poll also found that a large majority of Americans are concerned about an endless war with Iran. This is America -- the only things we want to be endless are shrimp at Red Lobster and seasons of ‘Grey’s Anatomy.’” - Jimmy Fallon

On Trump’s WH Correspondents' Dinner Debut
“And let’s just say Iran’s not the only thing he bombed,” said Seth Meyers. “Oh, my God. That room was so quiet. Is the audience sitting behind four-inch glass? Until they took a shot of the crowd, I just assumed everyone had left to go take a closer look at the ballroom.”

“You can both hear a pin drop and see people who look like they just sat on a pin.” - Seth Meyers

“During the same speech, President Trump told CNN reporter Kaitlan Collins to ‘smile more.’ OK, did you ever think she just doesn’t smile around you? That’s like saying ‘My wife never orgasms.’ Maybe she isn’t the problem.” - Seth Meyers

“People ask me all the time if I think Trump is good for comedy. I’ll say this: He’s better for it than he is at it.” - Seth Meyers

Deal or No Deal Iran
Trump held a cabinet meeting at Camp David to discuss the war in Iran. “I’m not saying that they’re out of ideas, but the best option they came up with was pinning the war on Dr. Fauci.” - Jimmy Fallon

“I read that President Trump was furious about the Iran war, and he’s been shouting curse words at his top national security officials. Yeah, his staff was like, ‘Is now a bad time to tell you that there’s algae in the pool again?’” - Jimmy Fallon

“Yep, the last time Trump was this angry was when McDonald’s added salads to the menu.” - Jimmy Fallon

“But the White House downplayed the report. They said the president just gets cranky when he misses his all-day naps.” - Jimmy Fallon

“Hey, you know how Trump’s been bragging about his cease-fire with Iran every day for weeks? Well, today he said it’s already over. Mm-hmm. Can you say something is over when it never really got started? That’s like me saying my relationship is over with Michael B. Jordan.” - Tiffany Haddish

“‘What do you mean, ‘Brought back into the war?’ We’re the ones doing the war. It’s like a tornado being, like, ‘Wah, why is it so windy in here? What’s happening?’” - Ronny Chieng

On Operation Pig in a Blanket
Trump left the NATO summit in Turkey on his old Air Force One instead of a new Qatari-donated Boeing 747-8 amid security concerns. Late night revealed more details about Trump's covert exit -- in a catering container – what Anthony Anderson called “Operation Pig in a Blanket.”

“Meanwhile, it just came out that when Trump left Air Force One, he took a few staffers with him but left Marco Rubio on board. To be fair, Trump forgot that he put him in the overhead bin.” - Jimmy Fallon

“Did they bring both Air Force Ones?” wondered Ronny Chieng. “Is that why there’s no gas in the world anymore? Because the president flies with an extra emotional support plane?”

“And, of course, we had to abandon the Qatari plane for security concerns. Of course that happened. This is why when it comes to the most important plane in the world, you don’t go certified pre-owned.” - Ronny Chieng

“Yeah, he hid in the back of a catering truck. Yeah, today, everyone was like, ‘Well, at least he has one exit plan.’” - Jimmy Fallon

“The whole thing seemed incredibly stressful, but, thankfully, Trump was asleep for most of it, so it’s OK.” - Jimmy Fallon

“Yeah, when Trump got out, officials were, like, ‘Wait, this catering truck was full when we put him in here.’” - Jimmy Fallon

“Trump went into a different plane, but he left his staffers and the press to fly on Air Force One. Yeah, everyone knew Trump was off the plane because it wasn’t flying at its normal 45-degree angle.” - Jimmy Fallon

“That’s the same way he used to get onto Epstein’s plane.” - Anthony Anderson

“Now, I’m no security expert, but if I was trying to find Donald Trump, a catering truck is the first place I’d look. Next time, hide his [expletive] in a bookmobile.” - Anthony Anderson

“Of course, all the people who were left on the plane are furious. Trump hasn’t felt heat like this since he locked himself in his tanning bed.” - Jimmy Fallon

On Wigging Out and Women in Waiting
Anthony Anderson, hosting Kimmel, addressed the “controversy” -- the seemingly fuller appearance of President Trump’s hair. “I’ve seen better weaves on ‘Real Housewives of Atlanta.’”

“Now, when asked about the hair, White House press secretary Karoline Leavitt said, ‘Lighting is everything.’ And she’s right. For instance, when you shine a light on the Epstein files, her boss’s name magically disappears.”

Trump announced that Leavitt is resigning as White House press secretary. “She said she wants to spend more time lying to her family,” said Anthony Anderson. “Leavitt has a toddler and a baby and a husband who’s 32 years older than her. So between that and working for Trump, it was just too many diapers to change.”

“We don’t know who the new press secretary will be or which beauty pageant she is the runner-up in. But if you’re interested in the job, send your résumé, head shot and cup size to 1600 Pennsylvania Avenue, Washington, Double-D.C.” - Anthony Anderson

“You’ve got to realize it’s time to hang up your wig and let Natalie tuck you in. Time to go nighty-night.” - Rosie O’Donnell, referring to Trump’s aide, Natalie Harp

On “Pinky Herman”
President Trump gave a speech at a Georgia high school where he likened the state’s Democratic senator, Jon Ossoff, to “Pinky Herman,” an apparent reference to the iconic man-child character “Pee-wee Herman.”

“‘Pinky Herman’ sounds like the guy who ripped him off on the reflecting pool.” - Jimmy Fallon

“You got to give Trump credit: He misspeaks in ways nobody ever thought possible.” - Jimmy Fallon

“Who the [expletive] is Pinky Herman? Is that some mobster from Queens who took you under his wing?” - Seth Meyers

On Mitch McConnell, M.I.A.
Speculation has surrounded the absence of 84-year-old Senator Mitch McConnell from public view since he was hospitalized with undisclosed health issues months ago.

“But apparently, people don’t like a majority senator disappearing with no explanation,” Ronny Chieng said, referring to calls for a “proof of life” video.

When, after weeks of silence, he provided a photo from a rehab center, Ronny Chieng said, “I think it’s pretty clear why he was admitted. He’s an incredibly old man. He’s half the age of America, all right? Look at him, he was probably diagnosed with, I don’t know, being extremely 84.”-

Jon Stewart called the image of the Senator seated next to his wife “totally believable evidence that Mitch McConnell is not only alive, but the happiest boy in the hospital. That’s the smile of a Make-a-Wish kid whose wish was that everyone else in the hospital lost their health insurance due to his [expletive] policies.”

“First of all, thank God he’s still hot as hell.” - Ike Barinholtz

“Yeah, nothing says perfect health like having someone hold you up when you’re already sitting. Looks like a husband-and-wife ventriloquist act.” - Jimmy Fallon

“In all seriousness, though, I do want to extend well wishes to Senator McConnell. I hope you get the quality health care you’ve fought so hard to deny everyone else.” - Ike Barinholtz

Not-So Party People
Trump celebrated America's 250th birthday along with a scattered crowd on the National Mall. Tiffany Haddish questioned the crowd size at the event, joking that “there was more people at my bat mitzvah.”

“I am going to be real honest with you -- there was more people at my D.U.I. trial.”

“Trump was forced to delay his Fourth of July speech due to the hot and stormy weather. In fact, some MAGA fans had to seek shelter in the African-American history museum. You’re welcome, again.”

“It was so hot outside, a bunch of white grandpas had to learn about Frederick Douglass. Found out that was they cousin.” - Tiffany Haddish

Goodnight Donny Boy
Rosie O’Donnell signed off from guest-hosting by thanking “everyone who’s been watching this week, especially the hungry, hungry hypocrite in the White House.”

“It’s kind of weird to think he spent more nights with me this week than Melania.”

“Most of all, I’d like to thank Jimmy Kimmel for inviting me to do this and for reminding everyone that we have the right to free speech in this country, whether Orange Voldemort likes it or not.”

O’Donnell also performed a new version of a traditional Irish ditty to close out her final monologue dedicated to a “very special boy.”

“[to the tune of ‘Danny Boy’] Poor Donny boy your polls, your polls are falling. 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? 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, why not resign, and make this country great again?” - Rosie O’Donnell

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