You could call it the night’s biggest twist: Sean Penn, who won Best Supporting Actor for One Battle After Another at the 98th Academy Awards, tying the all-time record for male acting wins, chose to spend it elsewhere. When Penn’s name was called at the Dolby Theatre, presenter Kieran Culkin stepped in, collected the Oscar, and delivered a perfectly dry observation about the absent winner. It was a moment both absurd and oddly appropriate for one of Hollywood’s most singular personalities.
Penn’s three Oscars join him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in a category that has remained static at three wins for decades. His previous wins were both for Best Actor — Mystic River and Milk — performances that defined their respective awards seasons. His third, for a supporting role, shows that Penn’s talent is not diminishing with time but simply finding new and demanding outlets.
One Battle After Another gave Penn the character of a rigidly ideological military officer, and he brought ferocity and precision to the role in equal measure. Director Paul Thomas Anderson had his own historic night, winning Best Adapted Screenplay and Best Director — his first Oscars after a career of critically celebrated but previously unrewarded work. Anderson’s wins drew prolonged and genuine applause.
Conan O’Brien was a sharp and warm host, opening with a topical joke about AI rendering human hosts obsolete and speaking thoughtfully about the global diversity of the nominees. Representatives from 31 countries — spanning six continents — made this one of the most internationally inclusive Oscars in recent history. O’Brien handled the ceremony’s heavier moments with the same ease as its lighter ones.
Michael B. Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio in a closely contested race. For Sean Penn, the 2026 Oscars were a night of triumph and indifference — in exactly the proportion his admirers would expect.
