Conan O’Brien Hosts a Night Sean Penn Won’t Forget — Even Though He Wasn’t There

The 98th Academy Awards had all the ingredients for a classic ceremony: a sharp host, major upsets, historic wins, and one significant no-show. Conan O’Brien delivered a witty and warm performance as host, Michael B. Jordan won Best Actor for Sinners, Paul Thomas Anderson finally won his first Oscars, and Sean Penn claimed his record-tying third award for Best Supporting Actor in One Battle After Another. The only person missing from the celebration was Penn himself.

Penn’s absence was acknowledged with humor by presenter Kieran Culkin, who picked up the award and quipped that the winner either couldn’t or didn’t want to attend the ceremony at the Dolby Theatre. Penn’s three wins now match those of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only male actors to have ever won three acting Oscars. His earlier victories were for Best Actor in Mystic River and Milk.

Penn’s role in One Battle After Another as a fanatical military officer was universally praised during awards season, with many critics citing it as one of the finest performances of his already distinguished career. Director Paul Thomas Anderson won both Best Adapted Screenplay and Best Director, his first-ever Academy Awards, completing an extraordinary night for a film that dominated the prestige categories.

O’Brien’s hosting drew broad praise. He opened with a joke about AI threatening to replace him, and spoke sincerely about the global nature of cinema, noting that nominees came from 31 countries on six continents. His performance struck a balance between entertainment and genuine emotional engagement with the evening’s significance.

Jordan’s Best Actor win for Sinners over DiCaprio added drama to a night already full of it. The 2026 Oscars will be examined and re-examined for years, not least because of the historical significance of Penn’s three-Oscar milestone — achieved, remarkably, from offstage.