Jimmy Kimmel was amused during his monologue on Wednesday night’s “Jimmy Kimmel Live” by the unexpected ties Sean “Diddy” Combs has to Donald Trump that have come out as part of his trial.

Media FLASHBACK: Kimmel joked with Diddy about running for president, said he’s a 'Boy Scout' compared to Trump Sean 'Diddy' Combs appeared in Manhattan federal court Tuesday where he pleaded ...

Jimmy Kimmel Jokes That Elon Musk And President Trump’s New Feud Is Like “Diddy vs. R. Kelly”: “I’m Not Sure Who To Root For” By Radhamely De Leon Published June 5, 2025, 4:28 p.m. ET ...

Jimmy Kimmel Says Trump Admin Would “Release Diddy” Before They Release The Complete Jeffrey Epstein Files By Radhamely De Leon Published March 6, 2025, 10:23 a.m. ET ...

Kimmel Jokes Elon Musk’s Rift With Trump Is ‘Like Diddy vs. R. Kelly’ | Video “Boy, when he’s off the ketamine, he is a lot less fun,” Kimmel says about the billionaire ...

Jimmy Kimmel joined in on the late-night host riff session tackling Elon Musk and President Trump’s escalating feud, which has seen the tech billionaire leave the administration and allege that ...

Jimmy Kimmel on ‘Dumb Guy’ Elon Musk Going ‘Nuclear’ on Trump With Epstein Accusation: This Ends With ‘One of Them in a Cell With Diddy’ ...

The epic blowout between Donald Trump and Elon Musk has delighted late-night hosts, but no one more than Jimmy Kimmel. On the latest episode of Jimmy Kimmel Live, the host noted, “This is so ...

Jimmy Kimmel on Tuesday night said Dr. Phil McGraw’s fawning interview with Donald Trump last week might not be what it seems. “Maybe he’s secretly screwing with him,” Kimmel said, and pointed to one ...