Kevin Connolly, Leonardo DiCaprio and Sean Penn attend Game Four of the Second Round of the NBA Western Conference Playoffs between the Los Angeles Lakers and the Oklahoma City Thunder at Crypto.com Arena on May 11, 2026 in Los Angeles, California.
Kevin Connolly, Leonardo DiCaprio and Sean Penn on May 11, 2026.
Leonardo DiCaprio, Sean Penn and Kevin Connolly sat together courtside at the Los Angeles Lakers' playoff game against the Oklahoma City Thunder in L.A. on Monday, May 11
DiCaprio and Penn recently costarred in One Battle After Another, while Connolly and DiCaprio have been friends since the 1990s
Penn won his third career Oscar in March for his supporting performance in One Battle After Another
Leonardo DiCaprio and Sean Penn are still hanging out, nearly two months after their movie One Battle After Another won Best Picture at the 2026 Oscars.
DiCaprio, 51, and Penn, 65, sat courtside with DiCaprio's longtime friend Kevin Connolly at the Los Angeles Lakers' playoff game against the Oklahoma City Thunder in L.A. on Monday, May 11.
The three actors were chatting throughout the match as LeBron James' Lakers were eliminated from the NBA playoffs' second round by the Thunder in four straight games. They were not the only celebrities on hand for the final game of the Lakers' season: Jessica Alba, Miles Teller, Tinashe and Max Baecker were also spotted sitting courtside.
Penn's appearance at the game appeared to be the first time he had stepped out in public in the U.S. since he won his third career Academy Award on March 15 for his supporting performance as the villain Steven J. Lockjaw in One Battle After Another.
He and DiCaprio portrayed foes in the movie, which won six Oscars in March, including Best Picture and Penn's Best Supporting Actor award.
Kevin Connolly, Leonardo DiCaprio and Sean Penn attend Game Four between the Oklahoma City Thunder and the Los Angeles Lakers in the Second Round of the NBA Western Conference Playoffs at Crypto.com Arena on May 11, 2026 in Los Angeles, California.
Kevin Connolly, Leonardo DiCaprio and Sean Penn attend Game Four between the Oklahoma City Thunder and the Los Angeles Lakers in the Second Round of the NBA Western Conference Playoffs at Crypto.com Arena on May 11, 2026 in Los Angeles, California.
Penn skipped this year's Oscars ceremony and was seen spending time in Ukraine the following day. He left the country to visit its president, Volodymyr Zelenskyy, as Ukraine's defensive war against Russia runs into its fourth year.
The actor was presented with an Oscars statuette made of metal from a train damaged during the war in the days following the awards show.
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Kevin Connolly, Leonardo DiCaprio and Sean Penn attend Game Four of the Second Round of the NBA Western Conference Playoffs between the Los Angeles Lakers and the Oklahoma City Thunder at Crypto.com Arena on May 11, 2026 in Los Angeles, California.
Kevin Connolly, Leonardo DiCaprio and Sean Penn attend Game Four of the Second Round of the NBA Western Conference Playoffs between the Los Angeles Lakers and the Oklahoma City Thunder at Crypto.com Arena on May 11, 2026 in Los Angeles, California.
Connolly, 52, and DiCaprio, meanwhile, go way back: the two men and Tobey Maguire have been friends since the 1990s. Connolly and Maguire, 50, were among the stars who attended DiCaprio's 50th birthday party in L.A. in 2024.
After One Battle After Another, DiCaprio is making his seventh film with longtime collaborator Martin Scorsese, What Happens at Night. DiCaprio costars in the movie with Jennifer Lawrence.