Conan O’Brien Jokes About AI While Sean Penn Makes History Somewhere Offstage

The 98th Academy Awards opened with Conan O’Brien’s jokes about artificial intelligence threatening his job, and it included a Best Supporting Actor win for a man who chose not to attend. Sean Penn won the Oscar for One Battle After Another, directing Paul Thomas Anderson’s third consecutive landmark film, and the award was collected by a visibly amused Kieran Culkin. Penn’s absence may have been unexpected to the casual viewer, but those who know him were less surprised.
Penn now holds three acting Oscars — the same as Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — and no male actor in history has ever won more. His previous wins were for lead actor roles in Mystic River and Milk, and this latest recognition for a supporting performance reflects his continued evolution as a performer. Not many actors can say they have won in both major performance categories.
One Battle After Another has been one of the most discussed films of the season. Penn’s portrayal of an obsessive, militaristic figure provided the film with its emotional engine, and Anderson’s direction kept the story taut and tonally precise. Anderson’s wins for Best Director and Adapted Screenplay were greeted with long, warm applause from an industry that has long admired his work.
O’Brien’s opening monologue covered everything from AI to international filmmaking, landing well with both the audience in the room and viewers at home. He called the ceremony a reason for optimism in difficult times, a framing that felt both genuine and necessary. The nominee pool, drawn from 31 countries, supported his argument.
Best Actor went to Michael B. Jordan for his remarkable performance as twin brothers in Sinners, a film that had also generated significant awards attention. DiCaprio’s defeat in that category was one of the evening’s bigger surprises. Penn’s absent win was the other.