Brooklyn, New York — Matt Damon made a surprise appearance on “Jimmy Kimmel Live!” on September 28, 2026, where he playfully disrupted the show while sporting a Boston Red Sox cap, showcasing the long-standing rivalry between the Red Sox and the New York Yankees.
As Kimmel kicked off the show’s week of broadcasts in Brooklyn, audience members were treated to his monologue, which included commentary on the impending baseball postseason. Just as he mentioned the Red Sox’ fierce competition against the Yankees, Damon, seated in the audience, shouted his support for his beloved team. “Go Sox! Go Sox!” he called out, escalating the energy in the theater.
Kimmel, recognizing the voice, quipped back, “You, the loser in the Red Sox cap, what is your name?” Damon cheekily responded, reminding Kimmel, “You know my name.” The late-night host then humorously dismissed Damon, ordering security to escort him from the venue, branding him a “Masshole,” a term used to poke fun at Massachusetts natives.
In a bid to defend himself, Damon claimed he wasn’t seeking on-air attention and was simply enjoying the show with family. Kimmel, however, pressed him on who he was with, leading Damon to reveal he was joined by Kimmel’s own mother and sister, Joan and Jill. The revelation prompted Kimmel to demand Damon’s immediate removal from the theater, firmly declaring, “Get him out of here right now!”
As security escorted Damon out, he couldn’t resist one last jab, teasing Kimmel, “You can keep me off the show; you can’t keep me out of your mom!” The audience burst into laughter, and Kimmel, once the disruption ended, jokingly advised the crowd to “get tested for HPV,” maintaining the light-hearted tone of the confrontation.
This playful banter is part of a running joke between the two men that has spanned nearly two decades. It began in 2005 when Kimmel, in a tongue-in-cheek apology format, would frequently claim that the show had run out of time to host Damon. Their rivalry reached a memorable moment in 2006 when Damon finally appeared as a guest, but Kimmel chose to cut him off and end the episode, keeping the feud alive.
Kimmel, who debuted “Jimmy Kimmel Live!” in 2003, has stated that the early years of the show were fraught with challenges, with many publicists hesitant to engage. Over time, he has relied on a close-knit circle of celebrity friends, including Damon, to draw viewers.
Though an effort for reconciliation took place in 2023, mediated by Ben Affleck, the peace was short-lived. The feud reignited dramatically during the 2024 Oscars when Kimmel aired a prank involving Damon’s Hollywood Walk of Fame star, re-establishing their playful animosity.
As Damon continues to navigate both his film career and family life, the actor remains an unpredictable and entertaining presence—not just in Hollywood but in the late-night television landscape as well.