The 98th Academy Awards: Where History Was Made and Seats Were Left Unfilled

Not every piece of history is witnessed by its maker. Sean Penn made his at the 98th Academy Awards from a location other than the Dolby Theatre, winning Best Supporting Actor for One Battle After Another and tying the record for most acting Oscars won by a male performer. Presenter Kieran Culkin collected the award on Penn’s behalf and delivered a memorably dry observation about the winner’s absence, drawing laughter and applause from the audience.
Penn joins Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in the record books with three acting Oscar wins each. His previous victories were for Best Actor in Mystic River and Milk. This latest win, in the supporting category for his role in a Paul Thomas Anderson thriller, adds extraordinary depth to a career already recognized among the finest of his era.
One Battle After Another placed Penn as a militaristic officer consumed by the very beliefs meant to guide him — a character of rich complexity that Penn brought to life with remarkable intensity. Director Paul Thomas Anderson claimed his first two Oscars for the film, winning Best Adapted Screenplay and Best Director on the same night. The wins completed a picture of a filmmaker at the very height of his powers, finally receiving formal recognition to match his long-established reputation.
Conan O’Brien’s hosting was enthusiastically received, blending sharp topical jokes about artificial intelligence with sincere celebration of the ceremony’s international composition. He noted that nominees came from 31 countries across six continents — an unprecedented reflection of cinema’s global reach. His performance helped make a historically dense night feel accessible and entertaining.
Michael B. Jordan took home Best Actor for Sinners, defeating Leonardo DiCaprio in one of the more surprising outcomes of the evening. The 2026 Oscars delivered records, upsets, and one legendary missing presence — all the elements needed to make a ceremony truly unforgettable.