Sean Penn Makes Oscar History, and Kieran Culkin Takes a Bow for Him

For the second year in a row, Kieran Culkin found himself deeply connected to the Best Supporting Actor award at the Academy Awards — first as winner, then as stand-in for Sean Penn, who won the category in 2026 for his role in One Battle After Another. Culkin accepted the award on Penn’s behalf at the 98th Oscars, delivering a memorable line about Penn’s absence that drew laughs from the crowd. It was one of the night’s defining moments.
Penn’s win was historic: his third Oscar places him alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis as the only male actors to win three acting awards from the Academy. Penn had previously won Best Actor twice — for Mystic River in 2004 and Milk in 2009 — giving him wins across both acting categories in his career. It is a distinction that very few performers can claim.
In One Battle After Another, Penn plays an obsessive military officer whose worldview slowly destroys him — a performance that critics called some of the most focused and powerful of his career. Director Paul Thomas Anderson also had a career-defining evening, winning both Best Adapted Screenplay and Best Director. For Anderson, who has been making acclaimed films for nearly three decades, it was a moment of recognition long in coming.
Conan O’Brien hosted the evening with his trademark wit and an underlying warmth. He opened with a pointed joke about AI replacing human hosts, connecting Hollywood’s immediate anxieties to a broader cultural conversation. His warm acknowledgment of the nominees’ international origins — representing 31 countries — helped establish a tone of global celebration.
Michael B. Jordan won Best Actor for Sinners, edging out Leonardo DiCaprio in what many considered the tightest race of the evening. Penn’s absent but history-making triumph overshadowed even that close contest as the night’s most enduring memory.