The ongoing rivalry between Matt Damon and Jimmy Kimmel reached a new high for Game 5 of the World Series with a unique twist.

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Damon, rocking a Red Sox hat, wore a red "I'm With Stupid" shirt, with an arrow pointing at his "good friend" to his left: Kimmel.

Meanwhile, Kimmel had a rebuttal of his own, donning a Dodgers-themed blue "I'm With Stupid" shirt, pointing right back at Damon for when they sat together for Sunday night's game.

Caught just outside of the fray? Damon and Kimmel's friend Ben Affleck, showing support for his Red Sox and finding himself in the center of the notorious Damon-Kimmel rivalry once more.

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Fulton DA Fani Willis (center) with Nathan J. Wade (right), the special prosecutor she hired to manage the Trump case and had a romantic relationship with, at a news conference announcing charges against President-elect Donald Trump and others in Atlanta, Aug. 14, 2023. Georgia’s Supreme Court on Tuesday, Sept. 16, 2025, upheld an appeals court's decision to disqualify Willis from the election interference case against Trump and his allies. (Kenny Holston/New York Times)

Credit: NYT