Jimmy Kimmel returned from his summer hiatus this week and wasted no time going back to the same well he’s been drawing from for years: Donald Trump. In his opening monologue, Kimmel mocked the President as “woke” and accused him of embracing cancel culture. The line made headlines, but the bigger story is Kimmel’s refusal to budge from the partisan content that has steadily driven away his audience.
The “Italy Rumor” Gag
The show opened with Kimmel addressing speculation that he was planning a move to Italy after gaining dual citizenship.
“Just to be clear, I’m not moving to Italy, I never said that,” he told his audience before adding, “I would move into Mar-a-Lago if I could, just to drive him insane.”
Jimmy Kimmel reading tweets from President Trump at The Oscars – YouTube, New York Post
It was a line meant to draw laughs, but it demonstrated what Kimmel’s brand has become: working Trump into nearly every punchline. For years, his ratings strategy has been to lean into politics, even as viewers tune out.
Trump, Colbert, and “Cancel Culture”
Kimmel then pivoted to the sudden cancellation of The Late Show with Stephen Colbert. CBS executives claimed the show was losing $40 million annually, but Kimmel framed it as political maneuvering tied to the network’s parent company seeking regulatory approval. From there, he turned back to Trump, mocking him for celebrating Colbert’s exit.
Stephen Colbert on The Late Show With Stephen Colbert – YouTube, The Late Show With Stephen Colbert
“Oh, you delicate, chubby little teacup,” Kimmel said to the president. “Did we hurt your feelings? You want us to be canceled because we make jokes about you? I thought you were against cancel culture? When did you become so woke?”
The joke drew attention online, but it also highlighted just how dependent his material has become on partisan combat. Rather than broad comedy, Kimmel’s nightly routines have settled into a predictable cycle of Trump digs and progressive applause lines.
Ratings Tell a Different Story
The problem for Kimmel is that viewers aren’t buying it the way they used to. In Q2 of 2025, Jimmy Kimmel Live! averaged just 1.77 million viewers. That puts him well behind Colbert’s now-canceled Late Show at 2.42 million, and only modestly ahead of Jimmy Fallon’s Tonight Show, which averaged 1.19 million.
Jimmy Kimmel performing a Monologue on his ABC show – X, @kylenabecker
Even worse, week-to-week ratings show a steep drop. Kimmel’s show recently fell to under 800,000 viewers in a week, a 26% plunge from the prior week. The same partisan formula that once gave him a temporary ratings boost has now become an anchor dragging him further down.
Colbert to Guest on Kimmel
Perhaps recognizing his slipping influence, Kimmel announced that Stephen Colbert will join him later this month during a week of shows filmed in Brooklyn. On paper, it’s a high-profile booking: two progressive late-night voices sharing a stage. In practice, it comes across as a publicity play, designed to capitalize on the attention surrounding Colbert’s sudden cancellation.
Greg Gutfeld appears on Jimmy Fallon’s The Tonight Show on August 7th, 2025
Meanwhile, Jimmy Fallon over on NBC recently stepped outside the echo chamber by inviting Fox News late night host Greg Gutfeld on his show, which popped The Tonight Show’s biggest rating in years.
CBS chose to cancel The Late Show not because Colbert lacked viewers—he led late-night for years with an admittedly declining audience—but because the economics no longer made sense. Between expensive production, falling ad revenue, and the fragmentation of audiences, even the top performer couldn’t justify the costs.
Late-Night’s Broader Decline
The struggles of Kimmel, Colbert, and Fallon (and Seth Meyers too…I guess…) reflect the decline of late-night television itself. Advertising for the format has fallen by more than half since 2018. Younger viewers are on YouTube, TikTok, and streaming services, where clips are consumed in bite-sized segments rather than full episodes.
David Letterman sits for an interview with Stephen Colbert – The Late Show With Stephen Colbert
Kimmel’s YouTube channel could rack up billions of views, but those online hits don’t translate into the kind of nightly audience network executives want. The genre as a whole has shrunk into a niche.
Conclusion: Clinging to Partisanship
Kimmel and his “Trump is woke” punchline made for an easy headline, but it did little to change the perception that he’s stuck in a rut. His ratings are sliding, his appeal is narrowing, and his insistence on partisan monologues has left him with an audience that’s loyal but shrinking.
Jimmy Kimmel speaks to Arnold Schwarzenegger on Jimmy Kimmel Live – YouTube, Jimmy Kimmel Live
Bringing Colbert on as a guest may buy him some buzz, but it won’t fix the deeper issue: late-night comedy no longer dominates American culture. For Kimmel, the more he leans on Trump for material, the more he risks proving that his show has little else to offer.
How do you feel about Kimmel calling Trump “woke?” Sound off in the comment section and let us know!
At least he acknowledges that woke people actively seek to cancel others. Still a disingenuous prick though.
Never forget: woke means saturated with left wing propaganda.
Kimmel, himself, is a fascist. Yes, fascists ARE left wing. (total govt).