Jimmy Kimmel’s fiery September 2 comeback on Jimmy Kimmel Live! turned weeks of Trump’s taunts into a blistering 10-minute takedown that mocked the president’s health, exposed his cancel-culture hypocrisy, and left the audience roaring while Trump fumed online — a clash that reignited late-night’s cultural firepower and left Washington buzzing.

Jimmy Kimmel returned to Jimmy Kimmel Live! on September 2, 2025, after his summer break, and instead of easing back into late-night comedy with lighthearted banter, he delivered one of the sharpest and most blistering monologues of his career.

For more than ten minutes, Kimmel devoted his opening segment to President Donald Trump, who for weeks had been lashing out at late-night comedy and personally targeting Kimmel in speeches and social media posts.

What followed wasn’t just a series of jokes — it was a televised showdown that lit up the internet, stirred political chatter in Washington, and had Trump’s team scrambling to respond.

The feud between Kimmel and Trump isn’t new.

The former president has repeatedly blasted late-night hosts as “talentless” and “unfunny,” while celebrating the cancellation of The Late Show with Stephen Colbert earlier this year.

In a rally held in Arizona in August, Trump even suggested that Jimmy Kimmel Live! would be the next show “sent packing.”

Kimmel, who had been quiet during his summer break, returned with a vengeance, showing no hesitation in turning Trump’s attacks back on him.

“Donald Trump has spent his summer vacation worrying about me,” Kimmel told his audience with a sly grin.

“Meanwhile, I spent mine on a beach, which I guess is one more thing he’s jealous about.” From there, the gloves were off.

He addressed head-on the viral rumors about Trump’s health that had been spreading online in recent weeks, poking fun at the images that sparked speculation.

“You’ve seen the photos,” Kimmel said, smirking.

“Big fat elephant ankles, swollen like two Macy’s Thanksgiving Day balloons.

And he wants to talk about me? Please.”

The audience erupted in laughter, with applause breaks stretching long enough for Kimmel to pause before delivering his next punchline.

But it wasn’t just physical jabs.

Kimmel skewered Trump on his well-worn rhetoric about cancel culture.

“Oh, you delicate, chubby little teacup,” he fired back, shaking his head as the audience roared.

“I thought you were against cancel culture? Weren’t you just bragging about canceling Colbert? Which is it, Don? Are you the victim, or are you the canceler-in-chief?” The biting line quickly went viral online, with clips of the moment spreading across X (formerly Twitter), TikTok, and Instagram.

Within hours, “#ChubbyTeacup” began trending worldwide.

The takedown continued as Kimmel mocked Trump’s constant fixation on ratings, noting that while Trump celebrated Colbert’s cancellation, Kimmel’s own program remains on air.

“Donald Trump measures everything by ratings,” Kimmel quipped.

“So let’s measure him.

How many times has he been arrested? How many indictments? How many trials? That’s not exactly a Nielsen win, Don.”

The crowd, clearly energized, broke into chants of “Jimmy! Jimmy!”

Insiders say the monologue wasn’t off-the-cuff.

Writers for Jimmy Kimmel Live! confirmed that Kimmel spent days shaping the opening, determined to strike back after weeks of insults.

According to one source close to the production, “Jimmy didn’t want to just tell jokes — he wanted to plant a flag.

This was about showing Trump that he’s not intimidated and won’t play along with his games.”

Trump, who was in Florida preparing for a campaign event, reportedly watched parts of the monologue and was “furious,” according to advisers.

Within hours of the broadcast, Trump posted a series of Truth Social messages, calling Kimmel “a sad, failing clown” and insisting that “no one watches his terrible show.”

Yet social media metrics told a different story: clips from the episode amassed more than 25 million views in under 24 hours across platforms, a staggering number for late-night television in today’s fragmented media environment.

Reaction from the political world was swift.

Supporters of the president dismissed Kimmel’s rant as “another Hollywood attack on real America,” while Democrats seized on the moment to highlight Trump’s thin skin.

Representative Alexandria Ocasio-Cortez posted, “This is why Trump hates comedians — you can’t sue a punchline.”

Meanwhile, conservative commentator Ben Shapiro criticized Kimmel as “proof late-night comedy has become left-wing activism.”

Yet beyond politics, the monologue reignited discussion about the state of late-night TV itself.

With Colbert’s departure and shifting viewing habits, many wondered if late-night comedy could still land a cultural punch.

Kimmel’s fiery return seemed to prove that, under the right circumstances, it could.

“This was the first late-night segment in years that felt like an event,” media analyst Tom Nichols remarked.

“It wasn’t just comedy, it was a moment of national conversation.”

As the applause faded and the monologue came to a close, Kimmel left his audience with one final jab: “So to recap, Don — you tried to cancel me, you failed, and now you’re trending for your ankles.

Welcome back to show business.” The audience gave him a standing ovation.

Whether this marks a new chapter in the ongoing feud between Jimmy Kimmel and Donald Trump or simply another entry in their long-running war of words, one thing is certain: late-night is paying attention again.

And in an era where politics and entertainment collide more than ever, Kimmel’s fiery comeback may go down as one of the defining television moments of 2025.