Jimmy Fallon and Trump didn’t see eye to eye a long time ago. Still, in recent times, the tensions between the two popular figures have drastically increased. Fallon took another swipe at Trump on The Tonight Show, this time drawing laughs by mixing Taylor Swift references with jabs at Trump’s rumored connections to Jeffrey Epstein.
In his August 13 monologue, Fallon joked about Trump’s recent meeting with Russian President Vladimir Putin. “Americans are worried Trump isn’t ready to negotiate peace in Ukraine,” he quipped, “because his mind is basically a giant ‘Blank Space.’”
Then things got more controversial. “Also, he’s distracted by the Epstein scandal,” Fallon said. “He’ll tell Putin it’s been a ‘Cruel Summer’ because everyone thinks ‘I Did Something Bad,’ but I swear everyone on the island was ‘22.’” as per The HuffPost.
The crowd reacted with a mix of laughter and shock. All these latest remarks come after various political events that happened with Trump. First, Fallon was referencing Donald Trump’s claim that he could quickly assess Russian President Vladimir Putin during talks about ending the war in Ukraine. Trump stated he would know “within the first two minutes” whether a peace deal was possible.
A comprehensive CNN review of Trump’s ties to Jeffrey Epstein—backed by records, photos, videos, interviews & messages—shows a long, close relationship until at least the mid-2000s. Epstein & multiple associates called them “best friends,” with Epstein saying Trump was his… pic.twitter.com/45EX2fYjII
— Andrew Kaczynski (@KFILE) August 12, 2025
Second, he mocked the Republican candidate regarding his recent scandal with the Jeffrey Epstein files. The s-x offender who was accused by several underage girls of s-xual abuse, leading to a controversial plea deal in 2008 that let him avoid serious federal charges in exchange for shorter jail time; however, under mysterious circumstances, he was found dead at the Metropolitan Correctional Center in lower Manhattan in August 2019.
Although Trump has not been investigated in the case, his past association with Epstein, which includes old pictures, instances, and texts, suggests that his name appears in some sealed documents, which may have influenced the administration’s decision to withhold additional disclosures.
NEW: A comprehensive CNN review of Trump’s ties to Jeffrey Epstein—backed by records, photos, videos, interviews & messages—shows a long, close relationship until at least the mid-2000s. Epstein and multiple associates called them “best friends,” with Epstein saying Trump was his… pic.twitter.com/eydHERORkO
— Andrew Kaczynski (@KFILE) August 13, 2025
Meanwhile, owing to Jimmy’s excellent comedy timing, he used Taylor Swift references from her songs to highlight the darkness and meaning that goes beyond the surface, just like Swift’s songs, who, by the way, also dislikes Trump due to his rude jabs at the billionaire pop singer. His last dig at Swift in September during his election campaign. Taylor was supporting his opponent, Kamala Harris. To show his reaction, he posted “I HATE TAYLOR SWIFT!” on Truth Social.
This is the context in which Paramount is acquiring the UFC media rights. They just paid $16m to Trump in a frivolous lawsuit and then got their merger approved, though Commissioner Anna Gomez didn’t like it.
The other two FCC Commissioners who approved it are Republicans. pic.twitter.com/1V9HW9vkgS
— Val Dewar (flyweight enjoyer) (@the3els) August 11, 2025
Recently, during an appearance on Sarah Silverman’s podcast, Jimmy Kimmel said that he might consider using his Italian citizenship to leave the U.S., expressing concern over what President Donald Trump might do to him. This remark comes after the POTUS indirectly mocked “Late Show” host Stephen Colbert. That’s not all, he also made rude remarks about popular hosts Jimmy Kimmel and Fallon.
Is #JimmyKimmel about to pull a Rosie O’Donnell and leave the U.S. because of #DonaldTrump? Well, if you were listening to #SarahSilverman‘s recent podcast, you just might think so.
🎥: The Sarah Silverman Podcast pic.twitter.com/gXLJlklrr3
— TMZ (@TMZ) August 11, 2025
“Colbert has no talent,” the president said. “Fallon has no talent. Kimmel has no talent.” In addition, Colbert’s show is confirmed to end after Paramount has paid $16 million and sought to finalize a major merger that required federal regulatory approval, after CBS wants to seal a deal with Skydance, a company that David Ellison, who happens to be the son of a well-known Donald Trump supporter, Larry Ellison, owns.
🚨 Trump secures a $16M cash settlement with Paramount, CBS and 60 Minutes, in addition to $20M in advertising. pic.twitter.com/Ne2LhwWr6X
— johnny maga (@_johnnymaga) July 22, 2025
Hence, everyone’s trying to impress Trump here except Jimmy Fallon. Still, knowing that Trump and Kimmel hold significantly different political views, we never know what fate has in store for his show.
