Jimmy Kimmel Complains About Free Speech, Then Takes Cheap Shots At Trump, CBS At Oscars

Jimmy Kimmel dragged his tired anti-Trump schtick to the Oscars, swiping at CBS, Trump and Melania onstage.

Only in the freest nation on the planet can someone take the stage during an awards show and bitch about a lack of free speech.

And only ABC could decide it was a good idea to bring Jimmy Kimmel out during the Oscars to take his usual shots at CBS and President Donald Trump, turning Hollywood’s biggest night into another one of his cheap political monologs.

The only difference this time? He did it on a Sunday instead of during his standard Monday-through-Friday anti-Trump routine. Somehow, the 58-year-old even made it through the bit without crying.

Kimmel took direct aim at CBS and the White House during his brief Oscars appearance Sunday night, tossing in a jab at Melania Trump for good measure while presenting Best Documentary Feature.

He opened with a crack about not hosting before sliding into references to "HIM" — Donald Trump — with all the grace and timing of a guy working through the same tired act for the thousandth time.

Even then, the audience clapped as if Kimmel had earned it.

"As you know, there are some countries whose leaders don’t support free speech. I’m not at liberty to say which. Let’s just leave it at North Korea and CBS."

Kimmel also took his dig at Melania Trump.

"There are also documentaries where you walk around the White House trying on shoes," he said.

Kimmel added, "Oh man, is he going to be mad his wife isn’t going to be mad about this," mocking the Melania documentary, which was released in January 2026, past the eligibility deadline for Oscars nominations, which rendered the joke useless.

ABC’s choice looked even more tasteless in light of Kimmel’s recent history. He is not far removed from the controversy that put his own show in the crosshairs after Charlie Kirk’s assassination, when his comments sparked enough backlash for ABC to suspend Jimmy Kimmel Live! indefinitely. Nexstar then went a step further, announcing that its ABC affiliates would preempt the show "for the foreseeable future," saying Kimmel’s remarks were offensive and insensitive. His judgment was already under scrutiny. Even so, ABC still decided Oscar night was the perfect time to hand him a microphone for another round of smug political theater.

"Mr. Nobody Against Putin" won the award Kimmel presented, with the documentary’s subject making a plea to "stop all wars."

Another night of Hollywood lauding itself as the bravest people on earth. It’s stranger than fiction.

Send us your thoughts: alejandro.avila@outkick.com / Follow along on X: @alejandroaveela

Written by

Alejandro Avila is a longtime writer at OutKick, living in Southern California. 

AA's thoughts on cinema, food, and SPORTS changed the lives of folks around the globe, baptizing them in the name of OutKick. Speaking sweet truth. 

All Glory to God (follow @alejandroaveela on X)