One of television’s longest-running fake feuds, Matt Damon finally took control of Jimmy Kimmel Live!, turning the tables on the host who has joked about bumping him from the show for years. The takeover, which involved a star-studded lineup of celebrities, included an interview with actor Gary Oldman, marking a memorable chapter in the comedic rivalry.
The Takeover Plot
Matt Damon’s hosting stint was an act of long-planned revenge. He kicked off the show by welcoming viewers to “Jimmy Kimmel Sucks,” joking about the novelty of having a host with “actual talent.” He explained his motivation, stating he had been bumped from the show “1,205 times” over a decade.
Damon replaced Kimmel’s entire team with his own A-list crew. Sidekick Guillermo was swapped for Andy Garcia, who humorously adopted Guillermo’s accent, and bandleader Cleto Escobedo III was replaced by singer Sheryl Crow. The monologue was even handed over to the late Robin Williams, in a previously recorded segment.
The plan hit a snag when Damon’s longtime friend, Ben Affleck, sabotaged the revenge by holding up cue cards that praised Kimmel as “funny, smart, good to his family and an excellent lover.” Affleck apologized to Damon, saying, “Forget it, Matt. I couldn’t do it to Jimmy!”
The Origin of the Feud
During the show, Damon explained the fictional feud’s roots. “Jimmy always wanted to be an actor,” Damon said, “and, unfortunately for him, I beat him out for every role he ever truly wanted.” The segment included fake audition tapes showing Kimmel trying out for roles in Damon’s films like Good Will Hunting, The Bourne Ultimatum, and We Bought a Zoo.
Celebrity testimonials poured in to support Damon’s hosting debut. Oprah Winfrey offered her endorsement, saying, “You have a gift, my friend. Not everybody can host a show. I know that is true. Great job.” Other well-wishers included Jennifer Lopez, Robert De Niro, and Don Cheadle.
Gary Oldman’s Serious Moment
Amid the comedy, the episode featured an interview with acclaimed actor Gary Oldman. While the specific details of their conversation during Damon’s hosted episode are not fully detailed, Oldman is no stranger to serious moments on Kimmel’s show.
In a 2014 appearance, Oldman used the platform to issue a broad apology for comments he made in a Playboy interview that were widely criticized. He told Kimmel’s audience:
“I said some things that were poorly considered. And once I had seen it in print, I could see that it was offensive, insensitive, pernicious and ill-informed. I don’t condone or excuse the words I used in any context. I just basically shouldn’t have used them in any context. But I did, and I have deeply injured and wounded a great many people.”
He called himself “an a-hole” who “should know better.” Kimmel lightened the mood by joking, “you are a great actor, so we can never trust anything you say,” to which Oldman replied, “Oh no, trust me.”
A-List Guests and the Final Jab
Damon’s guest list was a clear attempt to outdo Kimmel. Nicole Kidman declared she would never do Kimmel’s show because he “f–king sucks.” Other guests included Gary Oldman, Amy Adams, and Reese Witherspoon, who was supposedly brought in from the street after a trip to BevMo.
The final guest was Sarah Silverman, who Kimmel has long joked is Damon’s “f–king buddy.” When Damon, gesturing to the tied-up Kimmel, asked if she had anything to say to her ex-boyfriend, Silverman looked at him and simply said, “No, I’m good.”
The ongoing feud between Damon and Kimmel continues to be a source of entertainment, with Damon most recently crashing Kimmel’s show in Brooklyn in October 2025 disguised as a giant green mascot named Frankie Focus, proving their comic battle is far from over.
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