Sean Penn Makes Oscar History — and Eminem Wasn’t the Only One Who Stayed Home

Years ago, when Eminem won an Oscar for 8 Mile, the rapper famously watched from home with his daughter, having no idea he had won. Whether Sean Penn had similar domestic circumstances when he skipped the 98th Academy Awards is not known, but the parallel is hard to ignore. Penn won Best Supporting Actor for One Battle After Another while absent from the Dolby Theatre — and in doing so, became only the fourth man in history to win three acting Oscars.
Penn’s three wins tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. His previous victories were for Best Actor in Mystic River in 2004 and Milk in 2009, making the supporting win his third in a career that has been defined by complete commitment to the craft. Presenter Kieran Culkin collected the award on Penn’s behalf with a dry line that drew laughter from the audience.
Penn’s role in One Battle After Another — as a rigid, obsessive military officer — was one of the most discussed performances of the awards season. Director Paul Thomas Anderson, who made the film, had his own landmark night, winning Best Adapted Screenplay and Best Director — his first two Oscars after a celebrated career stretching back to the 1990s. For Anderson, the recognition was both long-awaited and richly deserved.
Host Conan O’Brien brought topical humor and genuine warmth to the proceedings, opening with a joke about being “the last human host” before AI takes over. He also celebrated the unprecedented international representation of the nominees — 31 countries across six continents — framing the ceremony as a global celebration of storytelling. His opening monologue set a tone of cautious optimism.
Michael B. Jordan beat Leonardo DiCaprio for Best Actor in Sinners, completing a night full of surprises. Between Penn’s absent record and Jordan’s upset victory, the 2026 Oscars gave audiences exactly the drama that makes the ceremony worth watching.